This list of things to do in East Sussex is sponsored by Classic Cottages.
When planning a weekend break in the UK, East Sussex might not be the first destination that springs to mind.
With the likes of Norfolk, the New Forest and the Cotswolds dominating the short break headlines, East Sussex is often overlooked – and unjustly so.
A warren of magical villages filled with ancient timbered homes, historic pubs and cobbled streets, East Sussex is easily one of the most beautiful parts of England. Add to this its proximity to the coast – lying just a stone’s throw from the golden dunes of Camber Sands and the eerily beautiful Dungeness – and East Sussex becomes the entire package.
With plenty of things to do in East Sussex, including trips to beautiful Rye, adventures in Winnie-the-Pooh’s very own Ashdown Forest and the chance to enjoy fish & chips in Hastings Old Town, a trip here is a fantastically wholesome one.
Below is our list of top things to do in East Sussex – including where to stay.
Luxury Cottages in East Sussex
Before we begin this list of the best things to do in East Sussex, a quick note on where to stay.
One of the reasons we visited East Sussex was to stay in a luxury cottage, booked through the fantastic Classic Cottages. Originally set up in 1977 by Tony and Clare, today Classic Cottages offer over 1,300 holiday cottages across the UK.
Importantly, these homes are not only incredibly family-friendly, but beautiful, too.
Having stayed with a number of UK holiday cottage companies over the years, we were incredibly impressed by the quality of the homes offered by Classic Cottages. Furthermore, we noticed that they were all incredibly reasonably priced (something not always guaranteed by their competitors).
As our weekend break to East Sussex would be our first time travelling as a six – our partners and toddlers joining us – we were keen to book somewhere suitably spacious. We were hoping to find somewhere that would offer both plenty of room for the kids to run around in, alongside enough bedrooms to ensure we weren’t all waking each other up during the night.
We were also after a big shared living space – one where we could cook, entertain the toddlers and relax with a glass of wine after bed and bath.
After much browsing of Classic Cottages’ properties in East Sussex, we came across the very handsome Castlemans Coach House.
Located in Sedlescombe, a short drive from Battle (the heart of 1066 country), Castlemans Coach House is the ideal luxury cottage for large groups – sleeping up to 8 (plus two cots for little ones). Once three buildings now beautifully combined, the Coach House provides plenty of space for large families, including a pretty garden and a generous outdoor entertaining area.
When we visited, we were blown away by just how characterful and high-end the house felt. Filled with ancient exposed beams, a roaring fire and a gleaming Aga, the Coach House seemed more like a luxury retreat, rather than a holiday cottage.
We had everything we needed for a (more than) comfortable stay, including: two Smart TVs, two living areas (one where the toddlers could play, another where the adults could relax) and – the most impressive feature – a ‘wing’ each.
This was particularly handy as we wanted to ensure Henry and Olive didn’t wake each other up at night – and so the fact that they were at opposite ends of the house was ideal. Next to their rooms, we both had a beautiful bedroom each, alongside our own bathrooms. This provided each family with a bit of privacy, if needed (or when we were hiding from our children).
Outside was a very inviting looking seating area, complete with BBQ and a place to enjoy some al fresco dining. As we were visiting in the depths of January, we didn’t quite make the most of this outdoor space – but can imagine that it would be idyllic come the long summer months.
Overall, the accommodation provided by Classic Cottages surpassed our expectations – and then some. As someone who has previously paid through the nose for other luxury cottages, all of which were of a similar standard to this wonderful Coach House, I will absolutely be using this company again (in fact, we are planning another short break as I type).
Things to do in East Sussex
So, perhaps like us, you’ve found the perfect place to stay (in our case, a luxury holiday cottage in East Sussex) and now you’re wondering what there is to do in this ancient county.
Thankfully, this small – yet historic – part of England packs a punch when it comes to sites and attractions. Whether that’s an amble to the local village pub, or a dystopian adventure across England’s only ‘desert’ – Dungeness, there’s something here to suit every type of traveller.
Below is our list of the best things to do in East Sussex.
1. Get to Know 1066 Country
Firstly, a brief introduction to East Sussex and its title – ‘1066 Country’.
In short, this part of the country derives its name from the fact that the famous Battle of Hastings, fought in 1066, took place here – in the (now aptly named) Battle.
The spot where a Norman-French army killed and defeated the Anglo-Saxon King, Harold – therefore signalling the start of the Norman Conquest of England – today Battle is a beautifully quaint (and decidedly peaceful) town.
However, the history of 1066 Country isn’t just limited to this infamous battle, but is a tapestry of other events and invasions, linked to towns and villages across East Sussex.
Thanks to its southerly position, this was where the Saxons and Romans first arrived. It’s where William of Normandy (William the Conqueror) also set afoot English shores, and where smugglers and thieves trafficked their goods and victims (weaving their way through the dark and dank Romney Marshes).
A county filled with crumbling castles, ancient battlefields and haunted inns, it’s thanks to this rich history that there are just so many things to do in East Sussex.
2. Visit Historical & Charming Rye
Easily one of the best things to do in East Sussex is to pay a visit to romantic Rye.
Sitting high above the myth-laden Romney Marshes, Rye is a small town filled with cobbled streets, leaning timbered buildings and ghost stories aplenty.
Once perched on the coast (before it was separated from the sea by marshland), Rye was the first call for invaders crossing the English Channel. Regularly defending its country against invasions from the French (and even the Spanish), Rye was soon given the esteemed status of a Cinque Port; providing it with certain royal privileges.
A place filled with shadowy winding lanes and one surrounded by dark marshland, Rye was also a popular hangout with smugglers and thieves, whose ghosts are said to still frequent some of the town’s oldest inns.
Today, and now some two miles from the sea, Rye is thankfully free of invading Frenchmen and thieves, and is instead a well-heeled and beautiful place to visit.
For most visiting Rye, their first stop is the historic – and incredibly photogenic – Mermaid Street. One of the most photographed streets in Britain, this cobbled hill, lined with medieval buildings and the famous Mermaid Inn, is hard to resist – especially in the summer months when the old houses are awash with wisteria.
Away from here, Rye’s high street is filled with eclectic independent stores and restaurants, including the fantastic Rae lifestyle store, the hipster-inspired Soap & Salvation and the beautifully styled Merchant & Mills (haberdashery store). Be sure to also pop by Knoops for some delicious hot chocolate and Whitehouse Rye, for a slap-up brunch.
During our own visit to Rye, we visited their small, but perfectly formed, cinema – Kino. Showing the latest releases, alongside classics and arthouse films, the Kino Rye is a fantastic place to come for a date, or with friends.
For those of you who love antiques, then be sure to head down the hill towards the river, where you’ll discover old warehouses filled with vintage stalls and antiques. Our favourite spots include Strand Quay Interiors and The Old Grain Store (complete with cafe).
Lastly, for the cosiest dinner in town – in the most welcoming and eclectic of pubs – then please head to The Globe Inn, Rye. This is perhaps one of my favourite pubs in the UK and it seems to get even homelier with each visit; with even more trinkets and memorabilia filling its nooks and crannies.
3. Visit Seaside Hastings
Just a few miles from Rye, lies its louder and bigger neighbour – Hastings.
A quick note, Hastings is divided into two distinct parts – the modern (and larger) part and Hastings Old Town, where I’d recommend you spend most of your time. This can be found just behind the seafront, tucked between two chalk cliffs (Hastings main town is a 15 minute walk away).
A muddle of clapboard houses, leaning medieval buildings and artsy stores – linked by ‘twittens’ (narrow alleyways to you and I) – the winding streets of Hastings Old Town are incredibly fun to explore – especially on a sunny day. As seagulls caw overhead, climb the town’s cobbled streets, stopping for coffee and cake along the way.
One of our favourite spots is Hanushka Coffee House, where we stopped for a quick coffee (and babycino for the toddlers). For book lovers, this is a great place for a quick browse of the latest releases. Alongside this sunny coffee spot, I also adore the many vintage and antique stores peppered throughout Hastings Old Town, including the bric-a-brac shops on Court Street, Butler’s Emporium and AG Hendy, which claims the title of Hasting’s ‘quirkiest shop’.
Outside of Hastings Old Town, one of the best things to do in East Sussex is definitely a visit to Hastings seafront and beach.
Its shingle beach – known locally as the Stade (an old Saxon word for ‘landing place) – is a busy area, filled with working fishing boats, Hastings’ famous Net Huts (where you can grab some great fresh seafood) and the unexpectedly interesting Hastings Fishermen’s Museum.
For those travelling with little people, the beach is a fantastic place to set up camp for the afternoon – thanks to the nearby park, fairground attractions and candy floss stalls. Hastings Pier, open during high season, is also a great place to take the kids.
On a clear day, it’s also well worth taking the East Hill Cliff Funicular on Rock-a-Nore Road. Said to be the UK’s steepest funicular railway, this lift provides quick access to Hastings Country Park. From here, you’ll be afforded spectacular views across Hastings Old Town and the coastline – all of which looks beautiful on a sunny day.
Lastly, a trip to Hastings would not be complete without fish and chips on the beach. Head to Maggie’s for the best fish supper in town.
4. Visit Camber Sands
One of the top things to do in East Sussex is definitely a trip to beautiful Camber Sands.
In stark contrast to the beach you’ll find at Hastings, Camber Sands is a vast expanse of rolling dunes and golden beach – filled with dog walkers, kite surfers and families building sand castles.
Although very busy come the summer months, the beach was almost empty when we visited one cold January afternoon. There are plenty of public car parks behind the dune system to park in, all of which you’ll need to pay to use (most close at 8pm).
For those hoping to cycle the length of the beach, you can hire e-bikes via Rye Bay E-bikes.
5. Visit the Home of Winnie-the-Pooh, Ashdown Forest
If you’re wondering if East Sussex is worth visiting, let this be your answer.
Nestled in the green depths of East Sussex lies Ashdown Forest – the real life 100 Acre Wood. Found in Hartfield, on the edge of the county, this beautiful forest is what inspired A.A.Milne to create Pooh’s magical home (he had a second home in Hartfield and visited regularly).
Alongside welcoming visitors hoping to explore the wider woodland, Ashdown Forest is very much geared towards Winnie-the-Pooh fans and includes a number of fantastic sites and attractions.
Definitely one of the top things to do in East Sussex is to visit Pooh Sticks Bridge, found inside Ashdown Forest. Built in 1907 and originally called Posingford Bridge, this is where historians think Milne and his son, Christopher, first played the game.
After years of wear thanks to its visitors, Disney paid £30,000 to replace the bridge – ensuring this site could be visited by Pooh fans for years to come. If you have little ones, this is a lovely place to walk to for a game – recreating Pooh and Christopher Robin’s favourite pastime.
Another (longer) activity is to take the Pooh Walk, that takes you through the real life 100 Acre Wood. This takes you to some of the main sites of Pooh’s adventures, including the Enchanted Place, the Sandy Pit, the North Pole and Eeyore’s Sad and Gloomy place (a long and short version of the walk are both available).
To start the walk, head to Gills Lap Car Park.
Lastly, no trip to Ashdown Forest would be complete without a ride on the famous Bluebell Railway. Comprising of one of the finest collections of vintage steam locomotives and carriages in the country, visitors to the railway are afforded the rare opportunity to climb aboard an old steam train and chug through East Sussex’s prettiest countryside.
The train’s timetable can be found here.
6. Afternoon Tea at Pooh Corner
While visiting Ashdown Forest, be sure to pop by the village of Hartfield itself – where Milne spent his holidays.
Not only a beautiful little place to stroll around, the village is also home to the wonderful Pooh Corner: a Winnie-the-Pooh themed tearoom.
Housed within a picturesque old building, built in 1703, Pooh Corner has been part of Hartfield since it was founded by Mike Ridley and his wife, June, in 1978. Nestled within the forested hills of East Sussex, the cafe not only offers Winnie-the-Pooh themed food and afternoon tea, but includes a lovely souvenir shop and small museum; dedicated to Pooh memorabilia from across the globe.
Pop by for a cup of tea in Piglet’s tea room and treat yourself to some Pooh-shaped toast (I can also recommend their afternoon tea and mouth-watering scones).
As parents to Winnie-the-Pooh enthusiasts, we may be slightly bias, but a trip here was definitely one of our favourite things to do in East Sussex.
7. Visit Eery Dungeness
Away from the cosy cottages of Hartfield lies Dungeness – perhaps one of the strangest places to visit in the UK.
Said to be the only ‘desert’ in England – lying on the rocky shores of England’s south coast – Dungeness is an isolated and desolate place, yet one also filled with creative and architectural triumphs.
Found on Kent’s southernmost tip, this tiny fishing town – one littered with with tin roof shacks, a nuclear power station and a (somewhat out of place) narrow gauge railway – is an intriguing place to visit.
Visit for a walk across Dungeness’ vast shingle beach – heading towards the looming lighthouse you’ll spy ahead. A Grade II listed building, this weather-beaten beacon offers visitors incredible views across Dungeness and the nearby Romney Marshes (it’ll cost you £5 to enter, with a child’s ticket setting you back just £3).
Along the way, you’ll find a few places to eat and drink – including the fantastic Snack Shack, selling super fresh seafood. Think lobster and crab rolls, smoked cod chowder and fisherman’s rolls (containing the catch of the day). Alternatively, grab a quick beer at the small railway station nearby, where you can enjoy the finest ales from Romney Marsh Brewery.
For those culture vultures amongst you, it’s also definitely worth visiting Prospect Cottage – the former home of film director, Derek Jarman. His garden – a maze of flint circles, drift wood and explosions of red poppies – is beautiful and the house itself is unexpectedly photogenic.
Lastly, and one thing we’d highly recommend is taking the RH&DR railway – from Dungeness to Dymchurch or Hythe. Known as ‘Kent’s Mainline in Miniature’, this little railway and steam train is just a third of the size of a standard locomotive – making it especially popular with families and children.
Taking you along the coast and, at times, seemingly through people’s back gardens, our own journey on the RH&DR railway was a truly lovely one and the toddlers absolutely loved it.
8. Lunch in Pretty Winchelsea
Visiting pretty Winchelsea has always been one of my top things to do in East Sussex.
One of the smallest towns in England, Winchelsea was once a central trading hub – until ‘Old’ Winchelsea was devastated by a storm in 1287 and ‘New’ Winchelsea was rebuilt upon a nearby hill.
New Winchelsea played an important role during the wine trade (from the 1300s onwards) and as such, a maze of wine cellars (or ‘undercrofts’) still run beneath the town’s many homes. Excitingly, you can actually tour these during your visit.
To really embrace Winchelsea’s past, head to Charles Palmer Vineyards for a tour and wine tasting session. They also put on a wonderful looking ‘Shanty Sunday’ during the summer months, offering fresh seafood and plenty of wine – as live music plays.
For lunch in Winchelsea, head to the lovely New Inn, before walking down the steep hill to Winchelsea Beach (a 30 minute walk).
389 comments
Your blog post inspired me to search on Classic Cottages for our next family getaway. We’re looking to book Castlemans Coach House for my mother in-laws birthday celebration in July ☺️
I would love to stay at The Whistler in Somerset.
Such dreamy looking destinations 😍
I would love to stay in the St Annes house nr Looe, those views! 💚
Challens Yarde looks like the most dreamy place to stay 😍
Would love you to recommend one for us four! We all need a break ❤️
They all resonate idyllic splendour. The locations are fantastically placed, Geographically. My choice @classic_cottages I was to win would be The North Bay Cottage at Bridlington, East Yorkshire. Love the coastline their.
Chapel Cottage would be so nice!!
The workshop near Malton!!
The cottages all look completely amazing. Staying in Apsley Cottage would be a dream come true!
Oo it would have to be Moss Farmhouse, Bodmin
This stay looks great might have to pay a vist there also
I’d love to stay at Sunnyside Isle of Wight
Great guides! Would love to take my husband to visit the Dannett House in Cornwall , it looks amazing , perfect start to retirement xx
Castlemans Coach House for me! 😍
Dannett House in Cornwall looks dreamy. I’d love to stay there
St Catherine’s House, Tenby, for me please
Moonstone would be amazing for a reunion!
The pigeon house would be a perfect getaway for me and my fiancé x
I would love to stay in the granary! Close to Bolney vineyard for me and bluebell railway for my daughter! 🙂 they all look amazing though!
I would love to stay in number 5 cottage in Ambleside, Lake District. I got engaged in Ambleside in 2015 and would love to go back with our two children 💗
Love the look of the Acorn Barn in Sussex from Classic Cottages amazing list!
I’ve honestly been swooning over that coach house you stayed in! Any of their cottages would be amazing!
Carzantic Chapel Barn in Launceston looks lovely 😍
I’ve been swooning over that coach house you stayed in! Any of their cottages would be amazing to stay in!
I would love to stay in the castlemans coach house after reading your blog, it looks beautiful and a perfect itinerary for us with a toddler in tow!
I would love to stay in the Jessie cottage in Sussex.
Lovely blog post, ladies- I’ve had a look at Classic Cottages and it’s Tredis House Barn for me! Gorgeous 💕
This is amazing all beautiful
Catlemans coach House
I would love to stay in the park farm cottage in the Cotswolds. I had a baby just before Christmas and my parents have been amazing in helping out, so I’d love to treat them to a little weekend away with the dogs
We are new to the UK, having come here from Goa and these cottages have such a nice, warm and homely feel to them. The Cornwall one looks particularly lovely
Would love to stay in a cottage with a sea view in Cornwall – spender Cottage in Mousehole looks amazing!
We would love to stay in old walls in Weymouth. We spent our honeymoon in Dorset last year with our four year old and had an amazing time, some of the best memories we’ve ever made. This year we’ll have a new addition so would love to recreate some of the magic!
Castlemans coach house!!
I’d love to stay at yhd Widgery in Devon ♥️
We’d love to stay at Orchard Dene in Croyde as this is our happy place!
Turner Hall- Dartmoor
I would love to stay in Yachtsman’s Cottage, my husband is from that area originally and we keep saying we will have a break down there.
Acorn Barn a little bit of luxury in a beautiful setting
LOVE Number 5 in Ambleside – Fingers Crossed here! x
Honey Badger Retreat would be so dreamy! Perfect place to rest & relax especially with the hot tub! Cornwall is my favourite place. As a nurse & with the cost of living we have had to miss our annual trip to Cornwall this year. My insta is katieloveskittycats to check I’m following ❤️
Wow so many beautiful places it’s hard to choose! But I’d go for the super unique California Dreaming Airstream so I could finally visit Durdle Door and explore the Jurassic Coast – would definitely take a dip in the wood fired hot tub too 😍
just so many lovely places to choose but Lady’s Well Shepherds hut near Weston Super Mare looks lovely
Moonstone in Cotswold looks magical!
After reading this article, anywhere in Easy Sussex. Looks beautiful
I so wanna go now!
The Fold near St David’s looks stunning 😍
The Willow near Westward Ho 😍 and dog friendly too, even better!
The Old Manor House, Charmouth, Lyme Regis 😊
So many really cute cottages on here. I’m in love with little Yeo in Devon and the old barn in East Sussex!
So many cute cottages. I’m in love with little Yeo in Devon and the old barn in east sussex
The Old Barn near Battle looks lovely, though I would probably use the voucher for somewhere in Yorkshire, maybe The Workshop in Malton
I love Cornwall and would love to stay at Spender Cottage in Mousehole x
Moonstone in Cheltenham would be ideal for a family get together – and an ideal location as it’s half way between London and the Midlands!
Woodville Cottage, Lyme Regis
Would love to stay at Little Seahill, Dorset
Piggy in the middle moreton in the marsh 🐖💖
Castleman’s coach house looks idyllic- open fire, Aga & wine fridge – what more could you wish for for a family break
I’d love to stay at Danny cottage, it look’s amazing
Stargazers retreat on the beautiful Isle of Wight
Love the look of Kinsale on the Lizard peninsula
Hi Paul! Congratulations – you were randomly selected as our winner! We have sent you an email, so we can put you in touch with Classic Cottages, who will be able to send you the £500 voucher. We hope you have a lovely holiday! Claire & Laura
Piggy in the middle!
I’d like to stay at Shore House on the Isle of Wight
Has to be the Jessie shepherds hut, so cute!
Seaward looks so beautiful and perfect for us to have a big, and long awaited, family get together
I would love to stay at Sawmill Cottage, it looks beautiful 😍
love the description of this one Southleigh House
The Wren’s Nest 😍 Gorgeous!
Hard to choose but Peveril, Morfa Nefyn in the top 5 😃
I’d love to stay at Castlemans Coach House!
The Piggery!
My mum turned 70 this month and I would love to take her to the lakes (which she loves) to say thank you for helping me out so much with childcare over the past 7 years for my two children! Although all of the places look amazing!
Number 5 in Ambleside looks gorgeous and a fab location too x
I mean, how could you possibly choose! But for me, anywhere with sea views in Cornwall instantly draws me in 🙂 Roughtor Barn looks glorious and I’d lovely to spend some family time there xxx
The thatched cottage Poorton House in Dorset looks absolutely stunning!
They all look fantastic, would love to stay at Castlemans Coach House and bring some friends!
The little London mews in Chichester would be great, right next to my favourite beach
I’d like to stay in the
The potting shed in Stamford
Towyn Cottage in Wales looks amazing
Me and my boyfriend stayed in a classic cottages shepards hut in Devon for my birthday and it was beautiful. Would love to do another stay like that again, yealm safari in Totnes looks fun
Piggy in the middle looks 👌
I would love to stay at The Whistler in Somerset.
All of the places look great and seems like you all had a fab time! Greycott, Westward or Bower Cottage would be ideal for an extended family break (with 2 under 2!) for my Mums 60th. Appreciate the curated selection of cottages. X
I would love to stay at Park Farm cottage
Yes 🙌🏻 All looking fab! But Cornwall one has me!
Piggy in the Middle in Moreton-in-Marsh.
Def the coach house!
I would love to stay at Bower Cottage
There’s so many gorgeous ones but I’d probably go for Lambs Lawn, would be perfect to go with the whole fam.. that climbing frame would tire the kids out early enough for a bev in the hot tub 🥂😁
Lake District for me!
A fab blog post and photos are beautiful! X
It has to be the Tawny Owl treehouse! There’s absolutely nothing better than an outdoor bath!
Acorns, Corfe Castle looks like the cottage for me!
Would love to stay at Castlemans Coach House! 😊
Isle of Wight for a first time visit!
Would love to stay at Castlemans Coach House! 😊
Eeyores cottage dartmouth, so cute and love winny the pooh! They all look wonderful though.
Eeyores house in dartmouth!
Moss Farmhouse! ❤️❤️❤️
Elm cottage looks idyllic 🥰
Great guides! Would love to take my husband to visit the Garden Cottage in Yorkshire 💕
Garden Lodge Wadebridge
Would love to stay in Peveril in Wales! Close to a pub and a beach, what more could you want!
I’ve not been to Devon for years so Coastguard Cottages in Ilfracombe on Classic Cottages looks perfect to me!
Ilfracombe would be a dream. I’ve been wanting to get back there for ages
Park Farm Cottage would be perfect for us
These cottages are gorgeous! Pooks Hill cottage in Devon appeals to me – I’m a sucker for a thatched roof, and it reminds me of a book I studied at uni (Puck of Pooks Hill)
They all look beautiful but I’m drawn to Pooks Hill cottage in Devon. I’m a sucker for a thatched roof and it reminds me of a book I studied (Puck of Pooks Hill)
I would enjoy my stay at the lovely looking Bower Cottage
Orchard Cottage looks fab.
The Twins blog post on Castlemans cottage sold it for me. Our toddler and baby would love it too.
St Catherine’s house, Wales. Amazing views.
I would love to stay in the Jessie Shepherd’s Hut near Battle (not just because of my name 🤪)- I’ve been wanting to explore this area for a while and feel even more inspired now after reading this!
O wow thesecall look amazing but the Castlemans Coach House would be amazing for my family x
The Wren’s Nest
Peveril in Gwynedd looks gorgeous 😍
The Old Stables near Chichester is calling my name!
I would love to stay in Pound Farm Cottage in beautiful Dorset… It looks like my dream home!
Lovely blog. I’m inspired and can’t wait to copy your itinerary on my trip to Norfolk in May! But for Classic cottages, Tikkidew cottage in Cornwall has been on my wish list for a while! 🥰
Bona-Vista in Cadgwith looks a proper job as they say in Cornwall!
I would love to stay at Daybreak Cottage near Port Isaac. I’ve only been to Cornwall once and the weather was stormy so I didn’t get to appreciate it in all its sunny warm beauty and would love to try it again!
I would love to stay at Daybreak Cottage, Port Isaac. I’ve only been to Cornwall once and it was stormy so i didn’t get to fully appreciate it in the sun and would love to go back and try again!
Great blog post, an area I’ve not visited in depth. I’d love to stay at The Pigeon! 🐦🙏
Layer de la Haye
St Catherine’s house in Tenby would be amazing for a family break for my brothers 40th this year! We need toddler and dog friendly!
The Week cottage looks fantastic! Would love to take my partner and dog and take lots of Amazing pics which we could share on Instagram!
Oceanix, Ventnor would be my choice.
So many lovely cottages but I’m drawn to the Lighthouse Keep in Dale, such amazing views.
I’d stay at the Gardeners Cottage in Dorset, it looks amazing!
Castlemans Coach House in Sussex – it looks beautiful for a staycation! X
Hard choice but Castlemans means we could take everyone!
Number 4 Coastguard Cottages near Ilfracombe
Gardeners Cottage in Dorset
Number 5 in the Lake District Ambleside my fave place!!
Beach House near Pembroke looks fantastic !
So many gorgeous cottages. If I had to pick perhaps Willows Rest, I love how baby friendly it looks yet tranquil and relaxing!
So many beautiful places to stay. I would absolutely love to take my little boy on his first holiday to the seaside and so If I could choose it would have to be somewhere with a sea view so we can spend our days watching the sea, the boats and the wildlife. Somewhere perhaps like Ocean view in Looe, Cornwall. I can dream 🥹💛🙏🏻
The Dairy,Settle.I have been trying to get up there for years,even losing a booking due to work and covid..Dark skys,trains,that landscape!,. A photographers dream..
Ocean view in Looe Cornwall is gorgeous. I grew up there and would love to go back
I’d love to stay in at Number 4 Coastguard’s Cottage – it looks absolutely beautiful and we love visiting North Devon.
Harbour Light in Boscastle
Cattleman’s Coach House – you sold it to me! ❤️
Castleman’s Coach House is stunning!
Orchard Cottage – although I feel I will want to totally redecorate my house when I get back 🙈
The Cobbles – Wadebridge
Beudy Gwyn (The White Cowshed) – it looks amazing, will hold our 3 dogs, surrounded by nature, close to the sea – lush!
Really enjoyed your blog and want to go to East Sussex now! I’d have to say the Coach house after reading it, it looks GORGEOUS. But to be honest, a lot of them do – including Looe with that sea view 😍
Buttercup in Cornwall. I’m sad that i’m not there right now.
North Cornwall to gain access to surfing so any family house in Bude
Would love to stay in North Cornwall as my in laws live near there and we go down there a lot. Would be lovely to have our own space to invite them round!!
Sea Blue House-Tenby
Moss farmhouse looks gorgeous!
Treboast Skyber
The park farm cottage in the Cotswolds 🤩
So many to choose from but Rectory Cottage in the Cotswolds would be dreamy.
Had a long weekend with two friends last year, it’s a good central point and would love to treat them to a getaway again!
No 5 Ambleside does it for me: wow!
The Castlemans Coach House – your blog post has me sold 🥰
I would love to stay at No 5 Ambleside for our first wedding anniversary!
I would love to stay at Moonstone in Cheltenham. It looks perfect, and those views. I can already see myself sat on the balcony in the morning with a coffee just watching the world go by and embracing the peace. PERFECT!!
The cobbles in north Cornwall with my family and little pooch to celebrate my dads 80th! looks so cosy and can imagine enjoying that beautiful garden!
The cottage in East Sussex for a weekend with my mum and sister and kids would be the dream!😍😍
The Tawny Owl Treehouse near Penrith is the perfect hideaway ✨
The Pigeon House looks lovely and cosy. Would be perfect for me, partner and baby. X
Minstrels is so pretty!
It’d be great to stay in The Granary, near Cuckfield village, with my little family :O)
Wow, so many amazing places to chose from – hard to narrow down. But Meadowcliff in South Devon looks fantastic for a group getaway!
I would love to stay in Squirrel Nutkin at Roe Wood
So many lovely cottages – I’d love a stay in The Old Barn, nr Battle
Would love to stay at Bossiney View, looks beautiful, though not sure our youngest could cope with the long car journey…but you can dream!
Would love to stay at Bossiney View, looks gorgeous
Moonstone 5128 looks absolutely amazing and it would be my first choice for a family get together!
Moonstone 5128 looks absolutely amazing and would be my first choice, for a fun relaxing family getaway!
Moonstone 5128 looks amazing and just perfect for a fun and relaxing family getaway!
I’d love to stay at North Bay Cottage in Bridlington
Oh wow! Wringworthy Farm would be perfect for getting our big family away together… we struggle to find places that fit us all but are still characterful and lovely.
Penally cottage in boscastle. What. A. Location. Breakfast on the patio with those views and immediate coast path access. Yes please!!
Number 5 in Ambleside
Love staying with classic. Would love to go back to lowenna just outside porthscatho. Has great memories for us as went when pregnant and when my boy was a baby. How he’ll be running around the orchard!
I just realised I didn’t put my full name. It’s Katie delay that put about lowenna
Number 5 in Ambleside – what a dream! 🥰
Great post! Would like to stay at the No 1 By The Sea in Dorset!
Great competition and post! I would love to stay at Chapel Cottage St Mawes in Cornwall with my little family this year 🥹🤍
Buttercup in Cornwall 💛
Chapel cottage in St Mawes looks like a dreamy stay 💭❤️
Hideaway Heath Hollow nr. Colchester
Would love to stay at the Cadena Cottage in Cornwall!
I’d love to stay at Towyn Cottage in Wales!
The Tea Hut near Crowborough looks amazing.
Sea view In Fishguard is beautiful and where I would choose
The Park Farm cottage in the Cotswolds looks amazing, and we love the Cotswolds!
Coastal view cottage in Brixham
The Wren’s Nest in Cumbria looks an amazing spot for my husband and I to get away from it all. The hot tub is an added luxury that I would love to experience!
Castlemans Coach house looks amazing!
I’d love to stay in Number 5 Ambleside with my family.
I think Daybreak cottage looks lovely. We love a relaxing cottage holiday, getting out and exploring a new place is always fun.
I would love to stay in Nolands Ho, Westward Ho! Devon with my husband and daughter and of course our little dog Louis. We would really appreciate a relaxing break by the sea
Tawny Owl Treehouse looks like a beautiful idyllic escape!
Ooh honestly I’d be happy to stay in any of them 🥰
Glas-Mor 9 St Margarets in the beautiful St. Ives, our favourite place. Always special, with so many amazing memories.
Arcus in the beautiful St. Ives. We’ve made so many happy memories in St. Ives and would love to go make more.
Castleman’s Coach House in East Sussex would be lovely 🥰
Willows Rest would be the absolute dream for some great family fun 😍
Poppets Cottage sounds perfect for the 2 of us.
Number5 Ambleside
Rectory cottage in the Cotswolds looks absolutely heavenly!! Perfect to take the kids and destress before my sons GCSE’s 🙂
The Acorn Barn in Sussex is gorgeous <3
would love to stay in Honey Badger Retreat!! (jellyefford)
I would love to stay at Rectory Cottage, near Stratford-Upon- Avon. Looks perfect.
Sea view (4432) would be perfect for our delayed honeymoon – wedding delays and busy work schedules have kept as waiting. We’re ready for a holiday and now that we’re moving closer to Wales, this cottage would be a dream for us and our dog Lulu! 🤩
The Acorn barn is just stunning and also looks so spacious and light. Alfriston is one of our favourite places. I’m just imagining the view of the valley from the barn…. Heaven!
The Park Farm Cottage in the Cotswolds looks lush and is dog friendly, bonus!!
I would like to stay at Syddyn Cowshed 4623
such a tough decision as so many amazing properties but as I have to choose it would be Seaside House in Little Haven, fabulous spot!
Piggy in the middle Morton-in-the-Marsh
Princes Granard, Devon please
Have stayed with Classic Cottages before in Devon 😀 – love the look of Meadows near Looe in Cornwall. Beautiful accommodation and a lovely location!
Challens Yarde in East Sussex looks gorgeous and it’s a part of the UK we’ve never explored.
The acorn barn in Sussex xx
Would love to stay at Castlemans coach house!
Love the look of Jasmine Cottage in Somerset!! Wow 🥰
Would love to stay in The Summer House in Perranporth
I would love to stay at Whitsand Bay View near Plymouth- it looks absolutely beautiful!
I would love to stay at Whitsand Bay View near Plymouth- it looks beautiful!
i’d love to stay at St Catherine’s House, Tenby
St Catherine’s House, tenby
treworgie mill, cornwall
I would love to stay at The Summer House in Perranporth, we all love going to Cornwall as a family!
love the look of North Bay Cottage in Yorkshire
Orchard Cottage in Cornwall looks like an amazing place to stay. A lovely property – Instagram name @tearoma
5 Valency Row looks amazing
5 Valency Row in Boscastle looks amazing
Would love to stay in The Bothy, Beaminister Dorset looks amazing.
Dog friendly Camber sands would be great.
Castlemans Coach House looks fab !
I’d love another trip back to the Lake District so number 5 at Ambleside looks great 🥰
I’d love to stay in St Catherine’s House in Tenby, Wales. The beach is my favourite place ever, I find it so calming and the house itself looks completely gorgeous!
I’d love to stay in the ‘drift’ cottage near Falmouth. I’ve never been to Cornwall so hoping to go on my upcoming maternity leave 🤞
The Cottage near Uckfield looks perfect for a getaway.
So many beautiful cottages, fab post! I’ve had a look and The Lookout in South Cornwall looks beautiful! Would love to go to one of these with my husband and two year old daughter. 💕✨
Piggy in the Middle in the Cotswolds (what a name)!
I’d love to stay in Pitt Lane Cottage, looks so cozy 😍
So many lovely cottages! Larch Barn looks amazing
The Lazy Bear Hideaway, looks a fun place to stay. Really switch off and connect with nature.
Dartmouth Lodge in Devon looks absolutely amazing! Have always wanted to visit Devon
Tawny Owl Treehouse in Penrith looks adorable!
Dannett House in Cornwall!
Friends Farmhouse in North Devon, looks great for a group holiday 🙂
I would love to stay at Daybreak Cottage, Port Isaac
Castlemans coach house 😍
The Bowjy in Cornwall looks amazing – anywhere in Cornwall would be beautiful ♥️
The Bolthole in Portscatho looks absolutely stunning!!
On another note just wanted to say love the blog, I work in travel and had my twins at a similar time to you having your little ones and it’s so lovely to see women being mums and still seeing the world! There’s more to think about now but we can still do it 💪🏽
The Song of the Sea
Castlemans coach house
Tregwelan Shepherd’s Hut
Yealm safari in Devon would be an amazing get away for us and our toddler 😍
Castlemans Coach House looks fab 🥰💕
I’d love to stay at 3 Little London Mews, it would be perfect
Peveril for sure!!
Ohh such a hard choice – so many too choose from perhaps Dartmouth Lodge though as I do love Devon.
Spinnakers on IOW for us – dog and toddler friendly for the win.
Acorn Barn, Sussex
It’s my dream to stay somewhere with enviable views – looks like The Sea House in Cornwall 100% fits the bill!!!
Number 5 in Ambleside I think! We got married in the Lakes last summer and it would be so lovely to go back! X
Ooh so many lovely cottages to visit , but I would go for ‘ Pebbles’ in Dorset , such a lovely part of the country and its dog friendly and looks stylish and lovely garden and conservatory. Would be lovely.
So many to choose from! We walked the SWCP last year and saw so many places we would love to return to, so I have chosen The Saltbox in Port Isaac.
Oh my goodness. The beach house in Pembrokeshire ❤️
Wow, all the cottages are beautiful. The Granary in Haywards Heath looks gorgeous and would be great to go a visit where my husband was born with our children ❤️
Oh, wow! Love your images of East Sussex. There are some really great classic cottage and it’s not a brand I’ve looked at before, so lovely to find. The absolute dream would be Moonstone in Cheltenham! I’m a bit of a fan of quirky architecture, and that place is just insane. Thanks for the inspo!
No 1 By The Sea in Weymouth
I’d be over the moon to stay at Mill House at Birdforth Hall ..so many amazing properties to choose from
There are so many gorgeous places!! It is so tough to pick just one! I have always wanted to stay in a Shepherds hut so I would probably choose Jessie’s Shepherds Hut near Battle! Such a gorgeous setting and perfect for a break away from reality ♥️
Beach house! Hot tub and near the beach. Fabulous.
I would love a break to Windsong-Morwenstow, it looks fabulous! I love St Ives!
I would love to take my family to St.Andrew’s in Yarmouth in the IoW.
Rose of the Cliff would be amazing for a big family holiday
Squirrel Nutkin at Roe Wood
So many great looking properties! Tawny Owl Treehouse looks gorgeous 😍
I would love to stay at The Bird Box…it looks so cosy and my Border Collie would love the location!
I’d love to stay at Forget Me Not Cottage on the I.O.W. We are a couple with a very active Toddler! This Cottage looks perfect for families! Our Daughter would adore making sandcastles on the beach! ⛱️ I have liked, commented, and shared on Facebook too!
Bay Tree Barn! 🌊💙🤞🏻
The shippon in dawlish would be my choice – so beautiful, it would mean all my maternal family could get together in my grandmas town for a special holiday. 🥰🌊
I would love to stay at the Jessie cottage in Sussex it looks fabulous and it’s not an area I’ve previously explored.
Halcyon Cottage, near Lulworth, such a treat, would love it.
Carzantic Chapel Barn in Cornwall!
Acorn Barn is my favourite so far
Number 5 Ambleside Cumbria sounds the perfect location for exploring the Lake District with my family and our beloved dogs too
I would choose Ambleside as were due a newborn anyday now & not going to get away any time soon. Would be lovely to spend some quality time with Family together!
We would love to stay at Beudy Gwyn (The White Cowshed) with the dogs!
Id love to win and stay at Varcoe in Cornwall as irs beautiful and has amazing sea views
https://www.classic.co.uk/holiday-cottage/desc-3243.html
What a lovely treat this would be! 💃 A much needed break and some lovely “me time” with the hubby as we have a newborn and craving for some “us time” together. This would SERIOUSLY be a DREAM prize for us! 😍 any place near Wiltshire would be magical!
Jessie looking intriguing!
Hill Farm Cottage near Battle would be a fab base for exploring the area
I would very much like to stay in Number 5, Ambleside.
Blackberry’s Jack’s wagon. Perfection !!!
I would love to stay in Eeyores cottage, would be so interesting to stay there with the history it holds.
Higher Carnon farmhouse looks perfect for my family. Our last holiday together ended up being cut short to one night out and coupled with all the tears, so maybe we could attempt a do-over with slightly older kids! 🙈
Halcyon cottage looks lovely
Halcyon cottage looks great
They all look amazing! But I love visiting Cornwall in the summer and Chapel Barn looks alot more luxurious than our tent!
All look great…maybe Roberts Row!
Would love to stay at the Piggery 🐷
❤️
We would love to go to “Piggy in the middle” in the Cotswolds. Who wouldn’t with a name like that! We would love to take our boys here on a lovely holiday ❤️
Varcoe, so stunning!🧡
Wrens Nest!
I’d love yo stay at Rectory Cottage in the Cotswolds .. I’d love to explore with my hubby
I would choose Number 5 in Cumbria as Id love to take my husband and my dog Leon to the Lakes!
I would love to stay in Piggy In The Middle in Moreton-in-Marsh. It looks amazing.
I’d love to stay in the stables cottage near Thirsk in north yorkshire. The hot tub looks so inviting 😍
Wow! So many gorgeous places! I’d love to stay in St Catherine’s House in Tenby.
Park Farm cottage in the Cotswolds looks lovely
I love the Battle area, it’s where my niece got married, so a stay at Castlemans Coach House with my family would be wonderful
They all look amazing! Hard to choose one but I’d say anywhere in the South with a sea view.
So many gorgeous cottages to choose from, but I think Goose Yurt is probably near the top of my list!
East Sussex is top of my list. Would love to stay there. 🙂
Leeward Cottage in Pembrokeshire would be beautiful 😍
Halcyon cottage looks stunning. By the coast with lots of walks. ❤️💐💚💐❤️
East Grnstead
Ridge house 🤞🏻
Celtic Blessing in Dorset looks wonderful
The Lodge is stunning. Staying there would be a fantastic experience.
Ty Angor in Pembrokeshire looks beautiful
I’d love to stay in Stargazers’ Retreat!!
I think moonstone would be a great place for a reunion!
Acorn Barn looks absolutely gorgeous!
Thimble Cottage in Cornwall looks nice
I’ve got great memories of holidays to the Isle of Wight when I was a kid so I’d love to take my boys there. Stargazer’s Retreat looks magical 😍
Thimble Cottage near St Ives looks great
North Bay Cottage
The Dairy
Hursey Gate Stables looks great.
Challens Yard
Number 5 Holiday Cottage in the Lake District looks lovely
I would absolutely love to stay at Number 5 in The Lake District ❤️ it is absolutely stunning, recently renovated and dog friendly – would make for the perfect escape away with the whole family 🤞😃
lodsworth rural retreat
Stargazers retreat would be amazing
I would love to stay in The Pigeon House in Lewes. It looks so cute
Castlemans Coachouse East Sussex please.it looks stunning
The Granary in yorkshire
The number 5 holiday cottage in the Lake District would be incredible! Love going paddle boarding and walking in this area, it’s beyond beautiful 🌊 ☀️
Piggy in the Middle in the Cotswolds is my favourite!
Copperas Shepherd’s Hut looks perfect for our first holiday as family of 3 and pooch
Copperas Shepherd’s Hut looks great for our 1st family holiday as 3 and pooch
The Beach Retreat 3665 as it looks amazing and I have never been to the Isle of Wight!
Ocean view in Cornwall looks absolutely stunning 😍 my fiance and little girl would absolutely love it!!
Rockaway in Cornwall looks absolutely AMAZING. Perfect for my little girl who has down syndrome. It looks very safe and child friendly for her 😊
I would love to stay in bridlington
Medley’s Barn near Crowborough looks like the perfect base for my family to enjoy and explore the area from
The Granary looks amazing!! Would love to be able to relax here.
4 Roberts Row 4823, near Rye looks good
Smugglers Cottage in Cornwall looks quaint, I love the beams. I can take my dog too!
The Alpaca hideaway looks amazing!
Beggars Roost , Isle of wight looks amazing. Dog friendly is perfect.
My wife and I would love to be chosen and go to Bumble Bee Barn in Taunton
Newclose Houseboat looks amazing, I would love to stay there
Peverel Gwynedd looks perfect!
I’d love to stay at Leat House in Devon!
I’d love to visit Piggy in the Middle in Moreton-in-Marsh!
Number 5 in Ambleside to walk some more Wainwrights 🙂
The Dannett House in Cornwall is perfect.
I’d love to stay in Varcoe. It looks stunning.
The Loft, in Coverack, Cornwall. I’ve walked past this gorgon cottage several times over the years whilst staying on The Lizard. It’s in the most amazing spot, overlooking the harbour and the beach. I would love to win a stay there.
So many wonderful places, we love the Isle of Wight and the Newclose Houseboat looks amazing for a stay
We love to stay on the Isle of Wight and the Newclose Houseboat looks perfect for us
Newclose Houseboat on the IOW looks amazing
Rectory Cottage looks amazing.
Would love to stay in Acorn Barn in Sussex.
Piggy In The Middle, Moreton-in-Marsh looks great and the Cotswolds are lovely
We love Sussex and classic cottages always have so many great cottages and locations to choose from. the Pigeion house looks Idyllic
House of Logs Totland
Sunset Cottage Isle of Wight looks dreamy 🤩
It’s got to be castlemans coach house
Carzantic chapel barn
Beech Cottage in Dorset looks heavenly! I’d love to take my family there!
Ocean View 5097 looks lovely for our next visit to the in laws
North Bay cottage in beautiful Bridlington would be perfect please
Varcoe looks amazing and that view!
Far View in north Cornwall.
https://www.classic.co.uk/holiday-cottage/desc-5204.html
Kernow River View, Cornwall looks absolutely stunning.
Rectory Cottage. Stratford Upon Avon, Perfect to visit family!
Dieppy Farm Cottage looks so cosy and snug
I’d love to go to Leeward Cottage in Pembroke with my partner and dog Kevin the German shepherd. We love the sea and long walks.
I love the look of Sunset cottage, a taste of luxury
Varcoe, Cornwall
Happy Place (Dedwyddfa) Who wouldn’t fall in love with the house name .
I would love to stay in Chick Cottage, Portscatho Cornwall. It looks amazing as do the views 🤩
St Anne’s in Looe would be perfect, it ticks all the boxes with the sea views but we also have friends near there so we really want to get back to see them after a lovely summer with them last year exploring the area
The Burrow, Wiltshire
I’d love to stay at the cottage you posted or the Jessie Shepherds Hut in Battle. ❤️
Magnolia Cottage, Wells in Somerset looks iddylic
Castlemans coach house would be amazing!