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Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winchelsea vacation rentals

A brick house with a small patio, a white door, and a wooden fence.

1. 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)
"A great stay in a lovely area. New Hope is close to the beach, shop and pub and is perfect for those with a dog. It's very comfortable and has all we needed and the enclosed outside area is so useful if you have a dog. There's plenty to do within a short drive and we thoroughly recommend it. Thank you!"
United States
Duncan Mackrill
The price is SAR 1,324
SAR 1,324 total
includes taxes & fees
15 Nov - 16 Nov
1 bedroom accommodation in Winchelsea Beach, near Rye
A mobile home with a covered porch, a fenced yard, and a paved driveway.

2. 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 SAR 362
SAR 1,046 total
includes taxes & fees
15 Nov - 16 Nov
White Haven - with 2 double rooms
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 SAR 1,856
SAR 2,227 total
includes taxes & fees
23 Nov - 24 Nov
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)
"Great, different experience. Would recommend."
United Kingdom
Karen
The price is SAR 733
SAR 733 total
includes taxes & fees
18 Nov - 19 Nov
Extraordinary Huts
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

5. 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 SAR 977
SAR 977 total
includes taxes & fees
15 Nov - 16 Nov
An unusual two-storey apartment with beams and an open fire.
A brick wall with a stone base, a wooden gate, and two planters with soil.

6. 3 Cinque Ports Street

3 Cinque Ports Street
3.0 star property
Rye
The price is SAR 1,939
SAR 2,327 total
includes taxes & fees
18 Nov - 19 Nov
3 Cinque Ports Street
A stationary RV with a small attached structure, surrounded by trees and illuminated by string lights.

7. Sleeps 2 With Garden, Firepit and bbq

Sleeps 2 With Garden, Firepit and bbq
2.0 star property
Hastings
The price is SAR 216
SAR 289 total
includes taxes & fees
16 Nov - 17 Nov
Sleeps 2 With Garden, Firepit and bbq
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
2 bedroom accommodation in Rye
A modern bedroom with a large bed, a bedside table, a desk, and a window.

9. 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 SAR 1,008
SAR 1,008 total
includes taxes & fees
16 Nov - 17 Nov
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A modern living room with a sofa, a coffee table, and a dining area with a table set for four.

10. 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.
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
A modern bedroom with a large bed, a sitting area with a chair, and a view of the garden through a glass door.

11. The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom

The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful accommodation, with lovely vaulted ceiling making it bright and airy High quality finishes all round Kitchen has everything you need and a bottle of milk waiting in the fridge was a lovely touch Tea bags, coffee pods, crisps and biscuits also provided Bed was comfortable and high quality bedding Lovely big fluffy towels and M&S toiletries provided. It was so quiet at night meaning a great night sleep A lovely stay and would recommend a trip to Caster sands and Rye center"
United States
Lynn B.
The price is SAR 952
SAR 952 total
includes taxes & fees
15 Nov - 16 Nov
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
A two-story brick house with a visible front door, a small porch, and a fenced yard.

12. 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 SAR 1,336
SAR 1,559 total
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house in soothing Playden Rye neighborhood
A greenhouse structure surrounded by yellow flowering plants.

13. 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 SAR 518
SAR 617 total
includes taxes & fees
15 Nov - 16 Nov
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

14. 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)
"Beautiful property and absolutely lovely host."
United States
Alyson B.
The price is SAR 571
SAR 675 total
includes taxes & fees
18 Nov - 19 Nov
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A river with a boat, surrounded by greenery and buildings.

15. 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 SAR 496
SAR 724 total
includes taxes & fees
16 Nov - 17 Nov
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
A row of white houses with red roofs by a calm water body, boats docked, and a red sign in the foreground.

16. 17 The Boathouse

17 The Boathouse
3.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
"A lovely stay in a lovely property within walking distance of Rye town centre "
United Kingdom
Tony
The price is SAR 1,695
SAR 2,033 total
includes taxes & fees
24 Nov - 25 Nov
17 The Boathouse
A room with a fireplace, a television mounted on the wall, and a door leading to another room.

17. 3-bed Camber Sands Cabin - Pool - Parking - Pets

3-bed Camber Sands Cabin - Pool - Parking - Pets
3.0 star property
Rye
The price is SAR 693
SAR 1,188 total
includes taxes & fees
22 Nov - 23 Nov
3-bed Camber Sands Cabin - Pool - Parking - Pets
A compact living space with a kitchenette, dining area, and seating area.

18. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
Camber
Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
A hotel room with a bed, two armchairs, a small round table with a vase of flowers, and a view of the outdoors through large windows with curtains.

19. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (156 reviews)
"Very spacious apartment with everything you require to make your stay comfortable. Have booked to return again several times this year. Great for someone working away for several days"
United Kingdom
Melvyn Spencer
The price is SAR 237
SAR 285 total
includes taxes & fees
15 Dec - 16 Dec
Osborne Apartments
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, (17 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 SAR 2,514
SAR 2,514 total
includes taxes & fees
15 Nov - 16 Nov
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

A room with a wooden chair, a large mirror, and a bathtub.
The George in Rye

The George in Rye

The George in Rye
Rye

10/10 Excellent

Perfect location and room. Very good breakfast and front desk staff tried very hard despite seeming inexperienced. It is overall a perfect choice for Rye.
United States
Anonymous traveler
Reviewed July 10, 2024
The George in Rye

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.