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

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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 12.032.877 ₫
14.439.452 ₫ total
includes taxes & fees
3 Sept - 4 Sept
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 5.374.815 ₫
5.374.815 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Extraordinary Huts
A dining area with a green staircase, a glass table, and chairs.

3. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is 12.573.006 ₫
15.087.607 ₫ total
includes taxes & fees
3 Sept - 4 Sept
3 Cinque Ports Street

4. Cabin - Sleeps 8 - Garden and Parking

Cabin - Sleeps 8 - Garden and Parking
3.0 star property
St Leonards-On-Sea
The price is 5.639.584 ₫
7.402.947 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Cabin - Sleeps 8 - Garden and Parking
A large field with tents and a central fire pit, surrounded by a building with conical roofs.

5. Oastbrook Glamping

Oastbrook Glamping
2.0 star property
Robertsbridge
10.0 out of 10, Exceptional, (1 review)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
United Kingdom
Sima
The price is 5.589.572 ₫
6.707.486 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Oastbrook Glamping
A view through a window with hanging fish decorations.

6. Rye House

Rye House
2.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
The price is 14.763.530 ₫
17.716.236 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Rye House
A compact kitchen with a stove, oven, sink, and wooden countertops.

7. 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 4.469.304 ₫
6.234.432 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Caravan With Decking&patio-8/10 Berth-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

The View Hotel

The View Hotel

8/10 Good
"A clean modern hotel. A good breakfast."
Kim 1-night trip
Posted 2 hours ago
The View Hotel

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.