Cottage vacation rentals in Winchelsea

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

We had a wonderful week at Easter at Cooden Cottage. Ella was amazing and even helped us find a lost dog! The house is spotless, and beyond our expectations. The flow of the downstairs through to an amazing kitchen, conservatory and completely fenced garden was perfect for us and our two large dogs and we had several family get togethers in the garden, surrounded by greenery. The beds, bedrooms and bathrooms were excellent with plenty is space. We met Ella twice and it is clear that she is passionate about giving her guests a really special experience, from thoughtful touches to all rooms to a lovely welcome pack. While there, she wants her guests to feel that it is space and she completely achieved that. We felt at home and will definitely be back. Thank you!

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.

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!

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

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.

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!

We stayed two nights at Amanda's charming cottage and had a wonderful time. The garden is absolutely beautiful and clearly well cared for – our dog Morty had a great time exploring, and we enjoyed some peaceful sunbathing on the lawn. The location is quiet and relaxing, with a few great gastro pubs just a short drive away. A perfect little getaway from the hustle and bustle of London!

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.

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.

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.

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!

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.

Lovely stay during half term. Great homely feel. All the amenities you need, lovely kitchen and outside space. Host was fab, very friendly ans great recommendations.

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.

Victoria’s cottage and the stunning location was absolutely superb. Victoria couldn’t be more helpful and welcoming and went out of her way to make for a fantastic stay. The cottage and grounds are beautiful and a short distance away from the lovely village of Mayfield. It’s clear why everyone rates staying so highly. I’m looking forward to a return visit soon.

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.

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! ☺️

Great stay. Lovely place in a beautiful area. Marie-Claire was a great host & really helpful

Really nice and tidy house, beautiful interior ans great location, easy check-in with everything provided. All round 5 stars

Fantastic place to stay and we’d definitely stay here again. Very clean and well stocked with amenities. The barn is on a farm which itself is lovely. Sheep and horses very friendly, as was Andrew :-).

Was an amazing cabin. Really beautiful and typical English countryside. We loved the area and nearby walks on public footpaths and other parks close by. We had great communication, however download everything and direction before coming close to the cabin, there is no cell reception there so we rang the door of one of the houses on the estate to ask direction to the stables. The owners recently moved but the new owner was very nice to help us in the right direction. Perfect place and lovely cottages, there is one small downside but it’s a bit common for the area. Don’t expect too much water pressure for the shower.

Jo’s cottage is perfect in every way, so well laid out and excellent amenities. I cannot fault it. Jo has thought of everything and is a very generous host, providing treats and amongst other things, eggs juice bread and butter. Upon entering through a side gate it’s like stepping into a fairy land, a private and beautiful garden and a cottage to relax and unwind in. So well positioned to visit numerous attractions and beaches. The swing seat is a wonderful addition, on a summers day and well into the evening during and after spectacular sunsets it’s a great place to unwind and take in a a gorgeous view. ‘Badger Cam’ is a must! We saw them all the nights we were there along with a fox and this is a great way to watch them uninterrupted. I would highly recommend Jo as a host and her beautiful cottage you won’t be disappointed. We hope to return soon . Thank you Jo

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!