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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchelsea holiday rentals

Cottage | Interior

Holiday Home in Winchelsea

Sparrows Den Lodge
3.5 star property
The price is 11.066.833 ₫
13.280.200 ₫ total
includes taxes & fees
6 Mar - 7 Mar
Sparrows Den Lodge
Economy Cabin, Garden View

Camping in Bexhill-on-Sea

Chestnut Meadow Camping
1.0 star property
The price is 2.441.027 ₫
2.929.232 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Chestnut Meadow Camping
Luxury Cabin | Living area | TV

Camping in Hythe

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.4 out of 10, Exceptional, (32 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is 4.452.978 ₫
5.343.574 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Pinewood Camping Pods - At Port Lympne Reserve
Outdoor dining

Aparthotel in Battle

White Hart Netherfield
2.0 star property
The price is 2.787.893 ₫
3.345.471 ₫ total
includes taxes & fees
3 Mar - 4 Mar
White Hart Netherfield
Classic Room | Private kitchen | Electric kettle

Aparthotel in Hastings

1066 Apart Hotel
2.0 star property
The price is 1.976.220 ₫
2.722.792 ₫ total
includes taxes & fees
3 Mar - 4 Mar
1066 Apart Hotel
Living area

Cottage in St Leonards-On-Sea

The Boathouse
3.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is 12.208.649 ₫
14.650.379 ₫ total
includes taxes & fees
5 Mar - 6 Mar
The Boathouse
The Hide Out | Living room

Cabin in Rye

Extraordinary Huts
3.0 star property
9.6 out of 10, Exceptional, (41 reviews)
"Escaping to the country has never been more fun and magical. The resident robin and all his many friends keep you in that chilled mindset. The town of Rye was 10 mins by car and full of historical charm. It was even being used for filming while we visited. We walked from Rye to Camber sands along the cycle path and there are frequent buses back. "
United Kingdom
Meryl
The price is 5.348.969 ₫
5.348.969 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Extraordinary Huts
Miscellaneous

Apartment in Bexhill-on-Sea

Bexlet
2.0 star property
8.8 out of 10, Excellent, (51 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is 2.312.792 ₫
2.775.491 ₫ total
includes taxes & fees
10 Mar - 11 Mar
Bexlet
House, 1 Bedroom, Garden View | Garden

Apartment in Ashford

Calm Private Annex in Ashford Ideal to Work, Rest & Explore
2.0 star property
7.4 out of 10, Good, (3 reviews)
"One night stay to visit local family. Very welcoming, met on arrival. Coldest night of the year so far and it was warm, cosy & comfortable. Owners live next door, attached house, easy parking, easy to find. Will possibly be return during 2026, central location for all our needs."
United Kingdom
Steve
The price is 2.739.691 ₫
3.287.630 ₫ total
includes taxes & fees
8 Mar - 9 Mar
Calm Private Annex in Ashford Ideal to Work, Rest & Explore
Children’s area

Cottage in Pevensey

Lilyrose Cottage
3.0 star property
10.0 out of 10, Exceptional, (1 review)
"All very good. However too many disabled parking spaces meaning too few for others"
United Kingdom
Graeme
The price is 12.706.481 ₫
15.247.637 ₫ total
includes taxes & fees
9 Mar - 10 Mar
Lilyrose Cottage
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 Hope Anchor

The Hope Anchor

10/10 Excellent
"Nice room in character with the area and the hotel. Friendly staff."
catherine A 2-night trip
Posted 1 day ago
The Hope Anchor

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 7 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 Pett Level Beach are a couple of lovely local spots to get outside and enjoy nature. High Weald 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.