Cottage holiday rentals in Winchelsea

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Popular amenities for Winchelsea cottage rentals

Cottage rentals with a hot tub

Top Guest favourite
Cottage in Smeeth
4.97 out of 5 average rating, 702 reviews

Evegate Manor Barn

LizRating, 5 stars3 days ago
We LOVE this place! Super relaxing, perfect surroundings. The garden is fabulous, we made the most of the sunshine this weekend!
Top Guest favourite
Cottage in Kent
4.99 out of 5 average rating, 288 reviews

Plantagenet: A Historic Country Cottage with Pool

JohnRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Chelwood Gate
4.87 out of 5 average rating, 262 reviews

Escape to quality and peace in East Sussex.

ClaireRating, 5 stars3 weeks ago
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.
Superhost
Cottage in Kent
4.92 out of 5 average rating, 103 reviews

Thatched Cottage Kent hideaway 3 Bed HotTub Haven!

OlgaRating, 5 stars2 months ago
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!
Top Guest favourite
Cottage in Icklesham
4.97 out of 5 average rating, 239 reviews

Blackthorn is a luxurious, rural retreat for two.

KevinRating, 5 stars6 days ago
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
Guest favourite
Cottage in Kent
4.95 out of 5 average rating, 279 reviews

Daweswood - Luxury countryside cottage, lake & tub

HarryRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Staplehurst
5 out of 5 average rating, 26 reviews

Beautiful, Summer Retreat + Hot Tub

DillRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Woodchurch
4.96 out of 5 average rating, 273 reviews

Romantic retreat with hot tub & woodburner

SherylRating, 5 stars3 days ago
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

Superhost
Cottage in Udimore
4.85 out of 5 average rating, 102 reviews

Charming rustic 16th Century cottage near Rye

ChrisRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Great Chart
4.99 out of 5 average rating, 355 reviews

Pretty Converted Barn with Private Sun Terrace and Garden

JamesRating, 5 stars2 weeks ago
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.
Top Guest favourite
Cottage in Hastingleigh
4.98 out of 5 average rating, 123 reviews

Hazel Tree Cottage. A secluded country retreat.

JonathanRating, 5 stars3 days ago
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!
Top Guest favourite
Cottage in Camber
5 out of 5 average rating, 111 reviews

No.2 Shepherd’s Cottages - steps from Camber beach

CatherineRating, 5 stars2 weeks ago
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! ☺️
Top Guest favourite
Cottage in Kent
4.99 out of 5 average rating, 104 reviews

Delightful pet-friendly oast with private garden

MelRating, 5 stars2 days ago
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
Guest favourite
Cottage in Hamstreet
4.94 out of 5 average rating, 293 reviews

The Old Piggery Orlestone cosy country conversion

JaneRating, 5 stars1 week ago
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.
Top Guest favourite
Cottage in Robertsbridge
4.93 out of 5 average rating, 269 reviews

Ideal for couples, dog friendly, beautiful views

FrancesRating, 5 stars5 days ago
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 😊
Guest favourite
Cottage in East Sussex
4.83 out of 5 average rating, 236 reviews

Contemporary Coastal & Country Retreat. Parking. 🐾

SarahRating, 5 stars1 month ago
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

Top Guest favourite
Cottage in Dungeness
4.99 out of 5 average rating, 187 reviews

Dungeness fisherman’s cottage full of character.

AmandaRating, 5 stars1 week ago
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.
Top Guest favourite
Cottage in Burwash
4.99 out of 5 average rating, 156 reviews

Countryside views/Dog friendly/secure garden

ElspetRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Beckley
4.83 out of 5 average rating, 207 reviews

Cosy self catering cottage near Rye

EdwinaRating, 5 stars3 weeks ago
Great stay. Lovely place in a beautiful area. Marie-Claire was a great host & really helpful
Top Guest favourite
Cottage in Marden
4.99 out of 5 average rating, 554 reviews

The Lodge

CaitlinRating, 5 stars2 weeks ago
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!
Superhost
Cottage in East Sussex
4.83 out of 5 average rating, 136 reviews

Cosy 2 Bedroom Cottage In Rye

Ran CampbellRating, 5 stars1 week ago
Really nice and tidy house, beautiful interior ans great location, easy check-in with everything provided. All round 5 stars
Top Guest favourite
Cottage in Brightling
5 out of 5 average rating, 151 reviews

The Long Stable: Rural, spacious, fast Wifi

DominiqueRating, 5 stars2 days ago
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.
Guest favourite
Cottage in Benenden
4.9 out of 5 average rating, 250 reviews

The Paper Mill Stables

JoanneRating, 5 stars3 days ago
Stunning location. Well equipped. Cute and cosy.
Top Guest favourite
Cottage in Pembury
4.97 out of 5 average rating, 230 reviews

A Cosy Cottage With A Fabulous View Close To TW.

JasonRating, 5 stars1 week ago
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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