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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchelsea vacation 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 P28,522
P34,227 total
includes taxes & fees
Oct 27 - Oct 28
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 P12,643
P12,643 total
includes taxes & fees
Oct 22 - Oct 23
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 P29,574
P35,489 total
includes taxes & fees
Oct 21 - Oct 22
3 Cinque Ports Street
A bedroom with a bed, a chair, a wooden table, and a potted plant.

4. 1 Bed - Sleeps 2 - Near Beach - Parking

1 Bed - Sleeps 2 - Near Beach - Parking
3.5 star property
Hastings
10.0 out of 10, Exceptional, (1 review)
"Absolutely brilliant stay. Apartment is brilliant and Nikki a superb host!"
United Kingdom
Stephen
The price is P8,107
P9,728 total
includes taxes & fees
Oct 29 - Oct 30
1 Bed - Sleeps 2 - Near Beach - Parking
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

5. 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 P5,193
P6,231 total
includes taxes & fees
Oct 27 - Oct 28
Chestnut Meadow Camping
A row of white houses with red roofs by a calm water body, boats docked, and a red sign in the foreground.

6. 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 P28,594
P34,312 total
includes taxes & fees
Nov 6 - Nov 7
17 The Boathouse
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 P8,844
P12,996 total
includes taxes & fees
Oct 19 - Oct 20
Caravan With Decking&patio-8/10 Berth-pet Friendly
A cozy living room with a sofa, a white furry chair, a wooden table, and a fireplace.

8. Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (40 reviews)
"Wonderful experience and accommodation"
United Kingdom
Lesley
The price is P10,076
P12,091 total
includes taxes & fees
Nov 2 - Nov 3
Pinewood Camping Pods - At Port Lympne Reserve
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

Majestic Hotel Eastbourne by Belvilla

Majestic Hotel Eastbourne by Belvilla

8/10 Good
"A lovely spacious room. Lovely seaview . Good running shower. Close to local amenities. Would have been nice to have clearer information about the restaurant on offer in the hotel and the bar opening times, as this seemed to be closed."
DIANE 2-night trip
Posted 3 hours ago
Majestic Hotel Eastbourne by Belvilla

Find out more about Winchelsea

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

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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.

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.