
Cottage holiday rentals in Winchelsea
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Top-rated cottage rentals in Winchelsea
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Popular amenities for Winchelsea cottage rentals
Cottage rentals with a hot tub

Evegate Manor Barn
We LOVE this place! Super relaxing, perfect surroundings. The garden is fabulous, we made the most of the sunshine this weekend!

Plantagenet: A Historic Country Cottage with Pool
We had a lovely week in Plantagenet and really cannot recommend it enough; the cottage really exceeded our expectations. The garden is phenomenal. It was a private and tranquil escape and our collie thoroughly enjoyed doing laps of the large garden despite the rainy weather. We loved it from the moment we arrived and didn't want to leave. The cottage is well equipped, has a great cosy ambiance with lots of indoor and outdoor game options no matter what the weather. The communication with Tim&Maite was friendly and responsive, we particularly appreciated the slightly late check out. We are hoping to book again soon with more of our family joining us.

Escape to quality and peace in East Sussex.
A lovely modern cottage, exactly as described and photographed. It was well kitted out and essentials were provided. The bed was super comfortable but just a gentle note that if you have any mobility issues the apex of the roof means that you cannot stand up straight around the bed and the bed is low but this was not a problem on our stay. Helena and Philip were both really friendly and helpful. My personal favourite touch was when Philip invited me to pick some roses from the cottage garden to take inside. The hot tub was a real treat but please be mindful that you are in someone’s back garden so not completely secluded if they are enjoying their own space. Highly recommend, we would definitely go back.

Thatched Cottage Kent hideaway 3 Bed HotTub Haven!
What a beautiful cottage! Exactly like on the photos, very charming. Surroundings are stunning, hot tub was a treat. The kitchen is very well equipped with anything you might need. Beds were comfortable and cozy. The conservatory was great to just sit and play board games and have lovely meals, was nice and warm and toastie in there and the views!! Pauline’s communication and response times were excellent, very friendly and accommodating. All I would suggest, if possible is perhaps to think of some sort of covers/shelter from the cold/wind by the hot tub. It was very windy and we still wanted to enjoy the hot tub, but it got very cold whilst inside. Some sort of coverings will work a treat. Pauline suggested some great pubs and things to do in the area. All and all my friends and I had a lovely stay. Thanks Pauline!

Blackthorn is a luxurious, rural retreat for two.
wow what a find, the main attraction for us was the peaceful setting, the open views from the decking area was beautiful, I'm the worst person for relaxing, believe me I relaxed, the swimming pool and hot tub was gorgeous, definitely going to go back, great hosts, great accommodation, beautiful location. Thank you Peter & Karen

Daweswood - Luxury countryside cottage, lake & tub
Me and my friends stayed for a long weekend. The house is beautifully furnished. Every bedroom is as nice as the next. Fishing was on our itinerary, and didn’t disappoint. The lake was very much private and the boats were a worthwhile addition. I (we) couldn’t recommend higher.

Beautiful, Summer Retreat + Hot Tub
We had the most beautiful weekend at Sage Cottage. Everything—literally everything—was lovely, from the complimentary chocolates to the treehouse. You could truly see and feel the love that went into it all. Alison gave us a warm welcome, which made us feel comfortable from the moment we arrived. Nothing was too much trouble for her, and her pets were absolutely adorable. I could go on and on, but you really have to experience this wonderful stay to understand what I mean.

Romantic retreat with hot tub & woodburner
Such a lovely place. Patio and hot tub were fab! Lovely gardens and surroundings. Julie and Brian made the stay as easy as possible by thinking of everything! Thank you so much!
Pet-friendly cottage rentals

Charming rustic 16th Century cottage near Rye
A lovely comfortable cottage with a wonderful garden and views. Loved Brenda's artwork on the walls and she gave us a nice tour of her studio. Perfect place to stay to explore the area - Rye very close and easy to get to Dungeness and Hastings. Good pub supper at the Kings Head which is only 15 minutes walk on public footpaths away from the road.

Pretty Converted Barn with Private Sun Terrace and Garden
Gorgeous cottage with lovely grounds. Great that both bedrooms have both king beds and en-suites makes all the difference. The hosts had given a really great welcome with apple juice, butter, milk, bread, eggs on arrival - such a lovely touch! The cottage really did have everything you needed.

Hazel Tree Cottage. A secluded country retreat.
Wonderful peaceful stay and friendly host. Comfortable cottage with nice enclosed garden and meadow for the dog. Lovely welcome hamper. Beautiful location with lots of lovely pubs and walks near by. You won’t be disappointed!

No.2 Shepherd’s Cottages - steps from Camber beach
We had an amazing stay at the cottage - it was clean, tidy, and SUCH a beautiful home. We loved the beachfront location, the homey feel, and the beds were so comfortable. The bathrooms were very modern and of course very clean also. Rosie went above and beyond, she made check-in/check-out super easy and stress-free. I messaged to ask if she happened to have spare logs/matches for the living room fireplace one evening and she kindly brought it all round to the cottage within just minutes! Thank you Rosie and family for an amazing holiday! We travelled from Scotland for a big family reunion in Sussex and had a lovely time in this cosy cottage! We will definitely stay here again when we’re next in the area! ☺️

Delightful pet-friendly oast with private garden
A super place to stay when exploring Kent and East Sussex, full of charm and character, clean and smart and perfectly equipped. The garden is very pretty and well tended, and nice and secure if you have a dog with you(or children). Our host was really helpful, and quick to respond to any questions. She certainly went the extra mile with fresh flowers to greet us in the house, along with a very generous welcome pack of goodies. I would recommend this as a top notch, traditional to Kent holiday home

The Old Piggery Orlestone cosy country conversion
Caroline’s studio cottage, in the grounds of her beautiful home, was just delightful. We chose it for its proximity to the Gusbourne vineyard but it was also an excellent base for other local attractions including Battle, Rye and Camber sands. We loved having breakfast in the small courtyard outside the cottage, and the interior was furnished very tastefully. Caroline was an excellent host and we would highly recommend this property.

Ideal for couples, dog friendly, beautiful views
Beautiful little cottage with all the amenities you could possibly want .we stayed here so we could explore the local countryside and this was a perfect base .we would definitely recommend This sweet cottage and will definitely be back to explore more .Thankyou Louise 😊

Contemporary Coastal & Country Retreat. Parking. 🐾
We spent a lovely long weekend at Wren Cottage, a relaxing and cosy place for myself and my two boys (aged 8 & 11) and my parents. The cottage is very comfortable and light, with everything we needed and Lou couldn’t have been more helpful. We had some mixed weather but enjoyed time in the garden, as well as visiting Winchelsea, Petts Beach cafe and Rye Nature Reserve. We also spent time in charming and very picturesque Rye and enjoyed a pub lunch at The Two Sawyers, just around the corner from the cottage. A seven minute drive from the cottage is Icklesham recreation ground, which was great for when the kids wanted to kick a football, play basketball and go on the swings/slides. We also spent our last day in Hastings Old Town, browsing the streets, shops and cafes and the kids enjoyed the funfair rides. Wren Cottage felt like a home away from home, and we all agreed spending time there was a highlight of our trip.
Private cottage rentals

Dungeness fisherman’s cottage full of character.
We had a lovely stay at the cottage. It was very clean and comfortable, with everything you could need provided for. Helpful local information and books were a bonus. Friendly communication and clear instructions were helpful. Dungeness is a unique place, and the cottage is so well situated for views, walks, very close to Prospect Cottage, Pilot Inn and Snack Shack. The little railway was great fun (we walked to the station). On our last night there was a storm and we watched the lightning over the sea and power station which was amazing! Thank you for being great hosts.

Countryside views/Dog friendly/secure garden
What a wonderful place! The cottage was beautifully appointed with great attention to detail and was spotlessly clean. Lovely garden which our two dogs appreciated. Sarah and Mark had kindly left us some eggs from their chickens, some jam and wine which was a lovely welcome. They are very helpful hosts. Would highly recommend and will hopefully return soon.

Cosy self catering cottage near Rye
Great stay. Lovely place in a beautiful area. Marie-Claire was a great host & really helpful

The Lodge
First time holidaying on my own and I couldn’t have asked for a more relaxing place for a week away. Julie was lovely and whilst she checked on me a few times, she wasn’t overbearing and allowed me to relax on my own. Lots of treats and nice touches made the whole stay feel very luxurious. Would definitely stay again!

Cosy 2 Bedroom Cottage In Rye
Really nice and tidy house, beautiful interior ans great location, easy check-in with everything provided. All round 5 stars

The Long Stable: Rural, spacious, fast Wifi
Such a lovely Airbandb in the middle of the English countryside! Lambs and resident horses graze next to the barn with fresh air and kind hosts. The barn is renovated with thought - both a bath and shower - open kitchen plan and loads of light. We enjoyed every minute and thank Andrew for his kindness.

The Paper Mill Stables
Stunning location. Well equipped. Cute and cosy.

A Cosy Cottage With A Fabulous View Close To TW.
We had a wonderful stay at the property. We took our nearly 3 year old daughter with us and she loved it. The use of the owners garden and the fact that we could pick the fruit within was a nice touch. The views of the High Weald Landscape to the north was beautiful too. Property had everything we needed and was very clean. Location was perfect for visiting Hever Castle, Chartwell, Scotney and Battle! There are so many other places to visit that we will definitely be back to stay again and explore the area further! Sarah was very welcoming also. Highly recommend!
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- Le Touquet
- ExCeL London
- Nausicaá National Sea Center
- Dreamland Margate
- Botany Bay
- Leeds Castle
- Hush Heath Estate & Winery/Balfour Winery
- Tankerton Beach
- Worthing Pier
- Calais Beach
- Brighton Palace Pier
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- Bodiam Castle
- The Mount Vineyard
- Wingham Wildlife Park
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- Drusillas Park
- Tillingham, Sussex
- Howletts Wild Animal Park
- Golf Du Touquet
- Rochester Cathedral
- Bedgebury National Pinetum and Forest
- Eastbourne Beach
- Ovingdean Beach