Cottage vacation rentals in Winchelsea

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Popular amenities for Winchelsea cottage rentals

Cottage rentals with a hot tub

Top guest favorite
The barn is framed by greenery, with a spacious lawn in the foreground. The exterior features a dark wooden façade and a moss-covered roof. Sunlight illuminates the tranquil surroundings, inviting relaxation in this rural setting.
Cottage in Smeeth
4.97 out of 5 average rating, 702 reviews

Evegate Manor Barn

LizRating, 5 stars1 day ago
We LOVE this place! Super relaxing, perfect surroundings. The garden is fabulous, we made the most of the sunshine this weekend!
Guest favorite
Cottage in Bexhill
4.86 out of 5 average rating, 22 reviews

Cooden Cottage - Seaside retreat, pets welcome

NicolaRating, 5 stars2 months ago
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!
Top guest favorite
A charming cottage is nestled within a lush garden, framed by mature trees. Sunlight filters through the branches, casting gentle shadows on the well-maintained grass. A swing hangs from one of the trees, inviting relaxation in a private outdoor space.
Cottage in Kent
4.99 out of 5 average rating, 287 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
A charming thatched cottage is surrounded by a well-kept garden, featuring colorful flower beds and neatly trimmed hedges. The cottage's white walls contrast with the natural thatch roof, while scenic green fields extend in the background, adding a peaceful countryside ambiance.
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 favorite
A wooden cottage is framed by well-maintained hedges and greenery. In the foreground, a hot tub is situated on a wooden deck, surrounded by potted plants and shrubs, with clear blue skies overhead adding to the serene atmosphere.
Cottage in Icklesham
4.97 out of 5 average rating, 239 reviews

Blackthorn is a luxurious, rural retreat for two.

KevinRating, 5 stars4 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
Top guest favorite
A serene outdoor area is showcased, featuring a clear blue pool surrounded by a spacious stone patio. A charming cottage stands nearby, complemented by lush greenery and trees that extend into the landscape, creating a tranquil retreat.
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 favorite
A rustic wooden sign carved with the name 'The Old Goat House' stands against a backdrop of greenery. Pebbles surround the base, and warm light from a sunset enhances the inviting atmosphere.
Cottage in Woodchurch
4.96 out of 5 average rating, 273 reviews

Relaxing retreat with hot tub & woodburner

SherylRating, 5 stars1 day 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!
Guest favorite
The image features a hot tub filled with bubbles, surrounded by a vibrant garden. Colorful plants and trees are visible in the background, along with well-maintained garden features. The clear blue sky overhead enhances the serene outdoor atmosphere.
Cottage in Hunton
4.91 out of 5 average rating, 45 reviews

Rural retreat-hot tub, wood burning stove

JoanaRating, 5 stars5 days ago
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!

Pet-friendly cottage rentals

Superhost
The entrance to the cottage is surrounded by a lush garden, featuring various flowering plants and greenery. A pathway leads to the rustic timber and brick structure, with wisteria draping gracefully along the exterior. Nearby trees provide shade, enhancing the serene outdoor environment.
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 favorite
A welcoming living space features a spacious light grey sofa adorned with colorful cushions. A blue area rug anchors the room, complementing a tufted coffee table. Decorative wall art is arranged above the sofa, while soft lighting from table lamps creates a cozy ambiance.
Cottage in Great Chart
4.99 out of 5 average rating, 354 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 favorite
A serene bedroom features a spacious bed dressed in white linens, complemented by two folded towels atop. Adjustable reading lights are mounted on the walls, and a window offers views of the surrounding greenery, allowing natural light to illuminate the soft color palette.
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.
Top guest favorite
A dining table is set with plates, glasses, and cutlery, creating a welcoming atmosphere for shared meals. Natural light streams in from an open door, illuminating the rustic wooden features, while greenery is visible through the entrance.
Cottage in Hastingleigh
4.98 out of 5 average rating, 123 reviews

Hazel Tree Cottage. A secluded country retreat.

JonathanRating, 5 stars1 day 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!
Guest favorite
A charming entrance to the country cottage is framed by lush green hedges and vibrant flower beds. A wooden door opens to a cozy outdoor seating area with a small table and chairs, inviting moments of relaxation in a picturesque garden setting.
Cottage in Hamstreet
4.94 out of 5 average rating, 292 reviews

The Old Piggery Orlestone cosy country conversion

JaneRating, 5 stars6 days 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.
Guest favorite
A charming cottage is surrounded by vibrant green foliage and blooming orange flowers. The red-tiled roof complements the rustic brick exterior, while large windows let in ample natural light. Lush plants frame the entrance, adding to the cottage's inviting presence in the countryside.
Cottage in Westfield
4.87 out of 5 average rating, 139 reviews

The Hay Loft, Idyllic Rural Sussex Retreat

RebeccaRating, 5 stars3 weeks ago
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.
Guest favorite
A light-filled living area features two red sofas, including a sectional. A wood-burning stove is positioned next to a woven basket. Natural light enters through three skylights and two windows, complementing the neutral walls and soft carpet.
Cottage in East Sussex
4.83 out of 5 average rating, 236 reviews

Contemporary Coastal & Country Retreat. Parking. 🐾

SarahRating, 5 stars4 weeks 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.
Top guest favorite
A cottage with a classic slate roof is framed by well-maintained greenery, including shrubs and flowering plants. The light-colored exterior is complemented by blue window frames and a central door. A wooden bench is positioned in front, inviting relaxation.
Cottage in Mayfield
5 out of 5 average rating, 150 reviews

Beautiful cottage in lovely setting

KevinRating, 5 stars1 week ago
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.

Private cottage rentals

Top guest favorite
A long wooden boardwalk extends over a wild shingle beach, bordered by areas of low vegetation. A clear blue sky is visible above, creating an expansive and open atmosphere. The horizon blends seamlessly with the sea in the background.
Cottage in Dungeness
4.99 out of 5 average rating, 186 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 favorite
A charming entry door is flanked by vibrant blooming flowers cascading from above. The door, painted in a soft hue, features a small window and is set against a clean white wall, with a clear blue sky in the background.
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! ☺️
Guest favorite
Remnants of wooden posts emerge from the gentle waters of a beach at sunset. The sky displays soft hues of orange and gray, complementing the serene landscape. The wet sand reflects the fading light, creating a calm atmosphere by the shoreline.
Cottage in Beckley
4.83 out of 5 average rating, 207 reviews

Cosy self catering cottage near Rye

EdwinaRating, 5 stars2 weeks ago
Great stay. Lovely place in a beautiful area. Marie-Claire was a great host & really helpful
Superhost
An ancient stone archway is visible, framed by rugged textured walls. The clock can be seen at the top of the arch, while a quaint road curves gently beyond. Charming houses, adorned with greenery, line the street, hinting at the neighborhood's character.
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 favorite
A serene rural pathway is framed by hedges on either side, leading into the greenery. The ground is covered with grass, and trees provide dappled sunlight, enhancing the sense of tranquility in the countryside.
Cottage in Brightling
5 out of 5 average rating, 150 reviews

The Long Stable: Rural, spacious, fast Wifi

CraigRating, 5 stars2 weeks ago
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 :-).
Superhost
The kitchen features modern white cabinetry set against exposed wooden beams, adding character. A black induction stovetop and built-in oven are integrated into a wooden countertop. Natural light fills the space through a nearby window, enhancing the functional layout.
Cottage in Benenden
4.9 out of 5 average rating, 248 reviews

The Paper Mill Stables

JoostRating, 5 stars3 weeks ago
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.
Top guest favorite
Cottage in England
4.98 out of 5 average rating, 193 reviews

Cottage with a view.

PatRating, 5 stars2 weeks ago
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
Top guest favorite
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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