A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchelsea vacation rentals

A mobile home with a white exterior, a covered porch, and a number 27 sign.

1. White Haven - with 2 double rooms

White Haven - with 2 double rooms
Winchelsea Beach
2.0 out of 10, (1 review)
"Check in was easy and location was good, thise are the only positives. The property is extremely dated and dirty. The furnishings in communal areas were torn, threadbare, stained, dirty and smelly. The carpets were dirty, covered in dog and human hair. There was mould above the shower and dirt and mould under the sink. The areas around the toilets were soiled with rusted old urine splashes. There was mould on one of the bedroom walls.The kitchen cupboard fascias were peeling and the handles all...
United Kingdom
Emma V.
The price is AED 351
AED 1,071 total
includes taxes & fees
30 Sep - 1 Oct
White Haven - with 2 double rooms
A brick house with a small patio, a white door, and a wooden fence.

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (12 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
The price is AED 1,426
AED 1,426 total
includes taxes & fees
30 Sep - 1 Oct
1 bedroom accommodation in Winchelsea Beach, near Rye
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

3. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is AED 1,659
AED 1,991 total
includes taxes & fees
18 Oct - 19 Oct
Sparrows Den Lodge
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

4. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (45 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
The price is AED 697
AED 697 total
includes taxes & fees
30 Sep - 1 Oct
Extraordinary Huts
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

5. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (13 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
The price is AED 623
AED 750 total
includes taxes & fees
26 Oct - 27 Oct
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A dining area with a green staircase, a glass table, and chairs.

6. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is AED 1,734
AED 2,081 total
includes taxes & fees
4 Oct - 5 Oct
3 Cinque Ports Street
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

7. An unusual two-storey apartment with beams and an open fire.

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
The price is AED 1,235
AED 1,235 total
includes taxes & fees
15 Oct - 16 Oct
An unusual two-storey apartment with beams and an open fire.
A wooden staircase leading to a backyard with a garden, a small shed, and a house with a sloped roof.

8. 2 bedroom accommodation in Rye

2 bedroom accommodation in Rye
Rye
9.8 out of 10, Exceptional, (6 reviews)
"Very comfortable accommodation and so central to shops and restaurants. Particularly loved the wood burning stove."
United States
Sheila Davies
The price is AED 1,162
AED 1,162 total
includes taxes & fees
2 Oct - 3 Oct
2 bedroom accommodation in Rye
A compact kitchen with a stove, oven, sink, and wooden countertops.

9. Caravan With Decking&patio-8/10 Berth-pet Friendly

Caravan With Decking&patio-8/10 Berth-pet Friendly
3.0 star property
Rye
5.4 out of 10, (3 reviews)
"I was disappointed with this stay. For the amount of money it cost, the caravan was not clean, was overcrowded and needs a lot of smarting up. You had to pay extra to have bedding which I think is unreasonable, particularly how much it cost per night anyway. Communication with the host was fine but not great. Unfortunately I won’t be recommending or returning to this property. "
United Kingdom
Kerry
The price is AED 442
AED 685 total
includes taxes & fees
11 Oct - 12 Oct
Caravan With Decking&patio-8/10 Berth-pet Friendly
A wooden balcony attached to a building with a large tree in the background.

10. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
Rye
10.0 out of 10, Exceptional, (2 reviews)
"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."
United Kingdom
Kerry H.
The price is AED 555
AED 633 total
includes taxes & fees
30 Sep - 1 Oct
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A modern bedroom with a large bed, a bedside table, a desk, and a window.

11. The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Had a great time, thank you very much ! Would definitely stay again! Good location, easy to get into Rye and surounds."
United States
Anonymous traveler
The price is AED 989
AED 989 total
includes taxes & fees
18 Oct - 19 Oct
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A river with a boat, surrounded by greenery and buildings.

12. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
Hastings
9.4 out of 10, Exceptional, (3 reviews)
"Excellent"
United Kingdom
Melanie G.
The price is AED 633
AED 910 total
includes taxes & fees
4 Oct - 5 Oct
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
A modern living room with a sofa, a coffee table, and a dining area with a table set for four.

13. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
Camber Rye
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful caravan. We went at Easter 2026 and there were beautiful Easter touches bunnies etc throughout the caravan. Chocolates and Proscecco were a lovely touch. Checking in process was seamless and they provided so much helpful information. Would recommend and will definitely be back for another stay. Dog friendly too, my dogs loved the warm cozy throws provided and enclosed gated decking area"
United Kingdom
Claire O.
The price is AED 838
AED 915 total
includes taxes & fees
30 Sep - 1 Oct
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

14. Chestnut Meadow Camping

Chestnut Meadow Camping
4.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (5 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is AED 304
AED 365 total
includes taxes & fees
2 Oct - 3 Oct
Chestnut Meadow Camping
A two-story brick house with a visible front door, a small porch, and a fenced yard.

15. Charming 3-bedroom house in soothing Playden Rye neighborhood

Charming 3-bedroom house in soothing Playden Rye neighborhood
Playden, Rye
10.0 out of 10, Exceptional, (1 review)
"Beautiful house and garden near Rye"
United States
Edward W.
The price is AED 1,310
AED 1,611 total
includes taxes & fees
30 Sep - 1 Oct
Charming 3-bedroom house in soothing Playden Rye neighborhood
A cozy living room with a sofa, a dining table set for two, and a small side table.

16. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is AED 2,036
AED 2,443 total
includes taxes & fees
4 Oct - 5 Oct
1A Coastguard Cottages
A modern living room with a grey sofa, a wooden coffee table, a TV on a stand, and light blue curtains.

17. Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.0 out of 10, Wonderful, (7 reviews)
"Lovely peaceful setting and the caravan had everything you would need and bonus being so close to Hastings"
United Kingdom
William E.
The price is AED 409
AED 1,129 total
includes taxes & fees
30 Sep - 1 Oct
Rhodown - sun on the terrace all round
A modern building with a curved facade, multiple balconies, and a grassy area in front.

18. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (56 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is AED 320
AED 385 total
includes taxes & fees
13 Oct - 14 Oct
Bexlet
A room with a fireplace, a desk, a chair, and a large window with a view of greenery.

19. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds
Hastings
8.0 out of 10, Very good, (5 reviews)
"We had a very pleasant stay at this spacious and comfortable home, which was well-suited for our larger group. The garden was a particular highlight, offering ample space and the added delight of fresh fruit to pick. The location is great, being within a short walking distance of the beach and sea (20mins). The property was generally tidy, there were a few spiderwebs which luckily didn't have any spiders. If these were removed it would enhance the experience. Parking proved somewhat challenging...
United Kingdom
Tabassum A.
The price is AED 278
AED 1,432 total
includes taxes & fees
8 Oct - 9 Oct
Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds
A dining area with a table set for a meal, surrounded by bookshelves and a television.

20. 4 bedroom accommodation in Pett

4 bedroom accommodation in Pett
Pett
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful one night stay at Holly Cottage with family. Location is great with pubs and tearoom close by. We all commented on how comfortable the beds were and how quiet the cottage is. Would definitely recommend!"
United States
Sarah Gunner
The price is AED 2,468
AED 2,468 total
includes taxes & fees
30 Sep - 1 Oct
4 bedroom accommodation in Pett
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchelsea Hotel Reviews

The Burlington Hotel

The Burlington Hotel

8/10 Good
"cashless ? seriously wrong . cash is legal tender cards are not . it is a shame as i went to a pub to spend cash instead . not one , should be a choice and not forced on us as you lost out on a few quid by us going elsewhere for a drink."
doreen 2-night trip
Posted 3 hours ago
The Burlington Hotel

Frequently asked questions

Can I find vacation rentals in Winchelsea?

Yes, we have vacation rentals near well known local attractions in Winchelsea, or you can select a more secluded option if you're looking for relaxation. Our travelers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What's the top vacation rental that Winchelsea has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This vacation home rental near Winchelsea offers an indoor pool, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Winchelsea?

With 14 Expedia vacation rentals, you're sure to find just the right place for your Winchelsea stay.

What’s there to see and do in Winchelsea?

Winchelsea Beach and High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach and St. Thomas the Martyr are other places to visit while you're in town.

What’s a vacation rental in Winchelsea like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchelsea. Vacation rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.