
Cottage vacation 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

Cheerful, bright, cosy period cottage with hot tub
Really enjoyed our weekend away, great communication from the start. Quite and quirky cottage, so peaceful even though it's on a road, this wasn't a problem for us.. The hot tub was amazing.. A great extra to the weekend...☺️☺️

The Granary at Coes Vineyard, East Sussex
A fabulous place! Peaceful and private. The surroundings were stunning and the accommodation was spacious and very special. The swimming pool, jacuzzi and gym were excellent and very clean and the games room impressive. We had an amazing few days.

Evegate Manor Barn
Larissa's place is wonderful and provided the perfect space for our needs. The garden is HUGE and access to the hot tub was a bonus too. The accommodation was well appointed with everything we needed and very homely. We had a very warm welcome and I would highly recommend this place to others.

Oak Cottage with private log fired jacuzzi hot tub
What a hidden gem of a place! We feel so lucky to have found Stable Oak Cottages and to have spent New Year there with our family celebrating our sons 18th. The place was gorgeous and the hot tub such a treat! The alpacas were great entertainment and the luxurious little touches from bath robes and sliders, to home baked bread and muffins were just wonderful. Highly recommend.

Plantagenet: A Historic Country Cottage with Pool
We enjoyed a wonderful long Easter weekend in this charming cottage. The space was cozy and perfectly appointed, lots of old charm - original cottage was built in 1550! - and special touches that delighted our children and made us feel like we were in quite a magical little space. The gardens are beyond gorgeous and just a lovely space to sit in the sunshine and watch our children play. It was a wonderful weekend filled with children’s laughter, bird song and cozy nights by the fire as a family. Thank you Tim & Maite for sharing your gorgeous cottage with us. The children are already asking we come back soon!

Blackthorn is a luxurious, rural retreat for two.
Thank you Peter and Karen for a wonderful stay at your property. It was everything we hoped, secluded and calm, peaceful and serene. your thoughtful touches (the eggs, milk and biccies plus tea and coffee etc), plus your helpful insights into the locality were really helpful and helped make our stay. We loved having the use of the hot tub and the pool and the veranda over the garden was so peaceful in the evenings. We would absolutely stay here again if you would have us!

Badgers Den - Covehurst Bay Holiday Cottage
The Badgers Den is by far one of the best places we have stayed in on Airbnb! Chris and Erick are amazing hosts, always helpful and responsive. The place is immaculate, clean and very homely. The gardens around are incredibly well maintained by Chris and Erick too! The pool, steam room and hot tub are such a great bonus, being able to use them at anytime is amazing! We will definitely be coming back!

Beautiful, Summer Retreat + Hot Tub
Alison was a friendly and lovely host. She offered picking me and my friend from the train station when we first arrived and also offered to give us a lift to certain places. It felt like she was our mother in a way that she took care and looked out for us. The communication between us was good, Alison had given me her number in case we needed anything. Alison had set up the treehouse for us so we could watch the sunset which was so beautiful and we had the hammocks out which was relaxing. I would 100% recommend, there’s a lovely Village called Cranbrook where the people are very polite and welcoming. We visited a restaurant named Jumeira which had the most tasty Indian food I have tasted. Overall was an extremely enjoyable experience in the countryside, I would definitely want to visit again!
Pet-friendly cottage rentals

The Stable Cottage on beautiful farm
The cottage was immaculately clean, comfortable, well-equipped, and very good value for money. There are lots of lovely walks from the doorstep. The Plough was very good and just a few minutes up the lane. We chose to eat in on our second night to make the most of the cottage and views. We hope to return again, with bikes next time.

Stylish family retreat, Rye, coast, sleeps 8
What a wonderful stay! Mr Catts house is in beautiful surroundings just outside of Rye. Perfectly located and extremely well equipped! We found it brilliant with our young daughter, everything is there that you need - even a proper cot! The house itself has everything required for a really comfortable stay and more! The beds are so comfy and the high quality bedding and towels felt homely. Ruth is a wonderful host! A glorious stay - Thank you!

Badger Cottage, Camber Sands
We had a great stay, the house was extremely clean and well maintained. There was a lovely basket of supplies left in the kitchen for us. We liked the fact the 3rd bedroom was separate and had its own bathroom. Beds were comfortable. It was an easy walk to the beach. Some people may find the dunes hard to walk over, there is a car park and flat access to the beach just up the road. We would stay here again.

The Hay Loft, Idyllic Rural Sussex Retreat
The Hayloft is a lovely cosy relaxing place, Amanda is very friendly and welcoming and has lots of knowledge of the local area, we had a great break with our children and dogs, watching the chickens in the garden and being able to see the horses from the kitchen window is a bonus , can’t wait to visit again .

Charming little workers cottage
Such a beautiful cosy perfect little place we fell in love with it the minute we walked through the garden gate, cute, quaint and abit like stepping back in time, an evening in front of the fire on the comfy sofa with a cup of tea after a very windswept walk across the nature reserve was an absolutely perfect Sunday, followed by a great sleep in the super comfy bed , and croissant and fresh coffee for Breakfast kindly left by Lynda who was such a lovely helpful host, we will absolutely be back to stay for longer in the summer, one of our most favorite Air bnb accomodations by far 🙂

Sissinghurst Cottage lovely countryside walks
We thoroughly enjoyed our stay at studio cottage as it was spotlessly clean, had lovely linen and towels, great dressing room, bathroom and kitchen which was well equipped for our requirements. The location was perfect for visiting local areas and the local village shop great for last minute purchases. Jackie was quick to answer any of our queries and accommodate our requests. We would highly recommend this lovely cottage.

Saltwater Cottage - Camber Sands near Rye
We booked Dani’s house to have a few days away with our 4 young granddaughters. The house was perfect. Very well equipped with lots of board games for the girls. We ate in every day and the kitchen/dining room was great for big family meals. The house itself is really pretty in a private, small estate, that is very quiet. It’s cosy and homey inside with lots of personal touches. The bus stop is just round the corner on the main road. The beach is about a 5 minute walk the other side of the main road. However the climb up the dunes takes a little longer…they almost did nanny in 😂. But it was absolutely worth the climb! Beautiful, never ending beach. There is an easier walk onto the beach next to the car park further down. Dani was very helpful at all times. She should be very proud of her lovely house. Anny London

Dot Cottage, cosy hideaway in the centre of Rye
Dot Cottage is a gem. Incredibly well located in Rye. Very close to everything yet very peaceful. You feel enchanted by the house even before you walk in. The decor has a quintessential English feel but very well done. Very considerate colour palette and you can tell that Catherine has put a lot of thought into every single detail. As a host, Catherine was very quick to respond to any query I had and very helpful. We visited a lot of her recommendations and they were all great. We had 3 amazing days in Rye. Thank you Catherine!
Private cottage rentals

Oat cottage, in a converted barn rural location
A cozy cottage near the stunning South Downs and Sussex coast. Our five-year-old had a very comfy stay, and we were just as comfortable. The location is perfect, with lots to see and do nearby — from countryside walks to charming villages. Katie was an excellent host, incredibly helpful and provided us with some wonderful local recommendations. A wonderful spot for both relaxing and exploring ⸻ Would you like a few alternatives for slightly different tones (like a bit warmer or even more polished)?

9 White Cottage
Excellent holiday cottage set in idyllic surroundings, each facillity Within the cottage were as described and we felt imeediately comfortable! Local restaurants were excellent so much so we eat out all week, so very well satisfied all round My contact at beachy head estate office (evie) was excellent in Handling our enquiries before and during our stwy, so Evie take a bow for a job well done

Cooden Cottage - Seaside retreat, pets welcome
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!

Walnut Tree Cottage - beautiful gardens!
Great cottage in a beautiful location. Garden, and the snowdrops were stunning. The only downside was the very low ceilings. Anyone of average height is likely to hit their head on the beam in the kitchen. This was mentioned in other reviews, and expected in an old cottage, but was not mentioned in the description.

The Long Stable: Rural, spacious, fast Wifi
We really enjoyed our Easter week stay at the The Long Stable. Andrew and his wife were very welcoming and supportive hosts. The location is idyllic, very quiet and private, even if other farm buildings are nearby you won‘t be disturbed and can make the most of the huge terrace. The cottage is very tastefully furnished and everything is to a high standard. All mod cons are available and the kitchen is fully equipped so wie could enjoy cooking ourselves as well as trying out some of the many pubs and restaurants within easy reach by car. You can stroll around the farm or nearby woods at your leisure, we particulary enjoyed saying hello to the newborn lambs one of which we were allowed to feed as well. The farm is ideally located to visit the coast (recommending Rye Harbour Nature Reserve), National Trust Sites like Sissinghurst or Bateman or simply enjoy the countryside…you really are spoilt for choice. We highly recommend The Long Stable and would love to return for a longer stay.

Cottage with a view.
We had the most amazing stay. The cottage was immaculate with so many thoughtful additional touches. The surroundings were peaceful with views to die for and Jo’s gardens were very pretty! The wildlife was amazing and we saw badgers and foxes up close! We only stayed for two nights while we were visiting Port Lymphe and the location was ideal… We highly recommend Jo and her cottage, we wish we could have stayed longer and we would love to return! Thank you so much!

Dairy Cottage , in walking distance to Rye
Lovely cottage. Very spacious. Nicely furnished. Good WiFi. The courtyard is a nice suntrap and was a secure place for our Yorkshire terrier to potter around. Jane could not have been more helpful. Will definitely visit again. Rye is a beautiful town. Very dog friendly. Enjoyed good wine and a splendid Ribeye steak at The George Inn.

Hop at Tipsy Cottages: a romantic rural retreat
We had a wonderful stay at Georgina's cottage! She was incredibly accommodating and helpful, making us feel right at home. The cottage itself is beautiful and offers a truly peaceful escape. We especially appreciated the thoughtful touches for our little one – the provided highchair was a lifesaver, and the books and toys were a huge hit! We highly recommend George's place for a relaxing and family-friendly getaway
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- ExCeL London
- Nausicaá National Sea Center
- Dreamland Margate
- Botany Bay
- Blackheath
- Leeds Castle
- Brighton Palace Pier
- Dover Castle
- Hush Heath Estate & Winery/Balfour Winery
- Tankerton Beach
- Bodiam Castle
- Drusillas Park
- Bedgebury National Pinetum and Forest
- Walmer Castle and Gardens
- Worthing Pier
- The White Cliffs of Dover
- Fort Fun
- Stay and Splash
- Tillingham, Sussex
- Adventure Island
- Ovingdean Beach
- Rottingdean Beach
- Rochester Cathedral
- Calais Beach