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

Our top choices for Winchelsea vacation rentals

Interior

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is P28,810
P34,572 total
includes taxes & fees
Sep 5 - Sep 6
Sparrows Den Lodge
Living room

2. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (44 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 P12,833
P12,833 total
includes taxes & fees
Sep 14 - Sep 15
Extraordinary Huts
Dining

3. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is P30,103
P36,124 total
includes taxes & fees
Sep 16 - Sep 17
3 Cinque Ports Street
Exterior detail

4. Cabin - Sleeps 8 - Garden and Parking

Cabin - Sleeps 8 - Garden and Parking
3.0 star property
St Leonards-On-Sea
The price is P10,502
P14,124 total
includes taxes & fees
Sep 29 - Sep 30
Cabin - Sleeps 8 - Garden and Parking
Exterior

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 P13,383
P16,059 total
includes taxes & fees
Sep 2 - Sep 3
Oastbrook Glamping
Interior

6. Rye House

Rye House
2.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
Rye House
Private kitchen

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 P10,671
P14,885 total
includes taxes & fees
Sep 2 - Sep 3
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

Ashford International Hotel & Spa

Ashford International Hotel & Spa

10/10 Excellent
"From check in to check out a wonderful experience. Food in the restaurant was beautiful, breakfast buffet maybe could do with more choice. The spa facilities were very good, although the facial treatment I received, I thought overpriced for 20mins. Overall the cleanliness, staff, location were perfect Will definitely book again."
Gail 4-night trip
Posted less than an hour ago
Ashford International Hotel & Spa

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.