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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchelsea vacation rentals

Flat-screen TV

1. Grogu's Rest - 2 bedrooms with decking sleeps 6

Grogu's Rest - 2 bedrooms with decking sleeps 6
Winchelsea Beach
8.8 out of 10, Excellent, (8 reviews)
"great stay again"
United Kingdom
lindsay r.
The price is AED 476
AED 1,209 total
includes taxes & fees
22 Aug - 23 Aug
Grogu's Rest - 2 bedrooms with decking sleeps 6
Exterior

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 AED 357
AED 1,090 total
includes taxes & fees
1 Sep - 2 Sep
White Haven - with 2 double rooms
Cottage | Interior

3. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is AED 1,689
AED 2,026 total
includes taxes & fees
5 Sep - 6 Sep
Sparrows Den Lodge
The Hide Out | Living room

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 739
AED 739 total
includes taxes & fees
7 Sep - 8 Sep
Extraordinary Huts
1 bedroom, iron/ironing board, WiFi (free), bed sheets

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 571
AED 709 total
includes taxes & fees
16 Aug - 17 Aug
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
Exterior

6. 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 1,155
AED 1,155 total
includes taxes & fees
3 Sep - 4 Sep
An unusual two-storey apartment with beams and an open fire.
Fireplace

7. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is AED 2,073
AED 2,488 total
includes taxes & fees
21 Aug - 22 Aug
1A Coastguard Cottages
View from property

8. Chestnut Meadow Camping

Chestnut Meadow Camping
4.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (4 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is AED 310
AED 372 total
includes taxes & fees
16 Aug - 17 Aug
Chestnut Meadow Camping
1 bedroom, WiFi (surcharge)

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 AED 1,007
AED 1,007 total
includes taxes & fees
16 Aug - 17 Aug
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Fridge, microwave, oven, stovetop

10. Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Caravan - Sleeps 8 - Pets Ok - Parking - Patio
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 525
AED 773 total
includes taxes & fees
2 Sep - 3 Sep
Caravan - Sleeps 8 - Pets Ok - Parking - Patio
Property grounds

11. 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 644
AED 951 total
includes taxes & fees
6 Sep - 7 Sep
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
Property grounds

12. 2 bedroom accommodation in Rye

2 bedroom accommodation in Rye
Rye
9.6 out of 10, Exceptional, (5 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 1,274
AED 1,274 total
includes taxes & fees
27 Aug - 28 Aug
2 bedroom accommodation in Rye
Smart TV

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 916
AED 1,045 total
includes taxes & fees
1 Sep - 2 Sep
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
Property grounds

14. Hillside retreat - 2 bedrooms sleeps 5

Hillside retreat - 2 bedrooms sleeps 5
Hastings
The price is AED 357
AED 1,090 total
includes taxes & fees
10 Sep - 11 Sep
Hillside retreat - 2 bedrooms sleeps 5
Miscellaneous

15. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (55 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is AED 367
AED 441 total
includes taxes & fees
6 Sep - 7 Sep
Bexlet
1 bedroom, WiFi (free), bed sheets

16. Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Bexhill
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic location, perfect flat!"
United Kingdom
Mark S.
The price is AED 545
AED 625 total
includes taxes & fees
15 Aug - 16 Aug
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Living area

17. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
South Beach Landings 0028
Exterior

18. 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 1,333
AED 1,605 total
includes taxes & fees
20 Aug - 21 Aug
Charming 3-bedroom house in soothing Playden Rye neighborhood
TV

19. Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.0 out of 10, Wonderful, (6 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 416
AED 1,149 total
includes taxes & fees
10 Sep - 11 Sep
Rhodown - sun on the terrace all round
Coffee/tea maker, fridge, microwave, oven

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

Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
Camber
The price is AED 1,219
AED 1,392 total
includes taxes & fees
14 Sep - 15 Sep
Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
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

Holiday Inn Ashford North A20 by IHG

Holiday Inn Ashford North A20 by IHG

10/10 Excellent
"Greeted by a friendly reception member, check in was quick and easy. Our room on level 2 a family room was perfect for us very spacious and modern would highly recommend. Breakfast options good as well if travelling near would stay again definitely"
Kevin 1-night trip
Posted 3 hours ago
Holiday Inn Ashford North A20 by IHG

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?

Converted barn / Oast House with amazing views and EV chargers: This vacation home rental near Winchelsea is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.