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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchelsea holiday rentals

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is RM1,861
RM2,233 total
includes taxes & fees
26 Oct - 27 Oct
Sparrows Den Lodge
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

2. 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 RM831
RM831 total
includes taxes & fees
2 Nov - 3 Nov
Extraordinary Huts
A row of white houses with brown roofs and a sandy beach in the foreground.

3. 16 The Boathouse

16 The Boathouse
3.0 star property
Rye
9.4 out of 10, Exceptional, (6 reviews)
"It was an amazing stay great acommidation and close to the little town ."
United Kingdom
Andrew
The price is RM1,814
RM2,177 total
includes taxes & fees
4 Nov - 5 Nov
16 The Boathouse
A compact kitchen with a stove, oven, sink, and wooden countertops.

4. 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 RM581
RM854 total
includes taxes & fees
4 Nov - 5 Nov
Caravan With Decking&patio-8/10 Berth-pet Friendly
A dining area with a green staircase, a glass table, and chairs.

5. 3 Cinque Ports Street

3 Cinque Ports Street
3.0 star property
Rye
The price is RM1,944
RM2,333 total
includes taxes & fees
30 Oct - 31 Oct
3 Cinque Ports Street
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.

6. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (155 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 RM299
RM359 total
includes taxes & fees
25 Oct - 26 Oct
Osborne Apartments
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

7. 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 RM341
RM410 total
includes taxes & fees
23 Oct - 24 Oct
Chestnut Meadow Camping
A modern building with a curved facade, multiple balconies, and a grassy area in front.

8. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (58 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is RM359
RM431 total
includes taxes & fees
2 Nov - 3 Nov
Bexlet
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

Cavendish Hotel

Cavendish Hotel

10/10 Excellent
"We found the staff very helpful and friendly. It would be better if the bar opened a bit earlier as we would have a snack and a drink. Our room was very clean and we felt comfortable."
Annette 3-night trip
Posted 21 hours ago
Cavendish Hotel

Find out more about Winchelsea

Search for holiday rentals in Winchelsea on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Winchelsea using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchelsea!

Frequently asked questions

Can I find holiday rentals in Winchelsea?

Yes, there are holiday rentals close to the most popular sights in Winchelsea, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

How many holiday rentals are there in Winchelsea?

With 14 Expedia holiday rentals, you're guaranteed 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 holiday rental in Winchelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchelsea. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.