Search Holiday Rentals in Winchelsea

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Winchelsea holiday rentals

Exterior
Sparrows Den Lodge

Holiday Home in Winchelsea

Sparrows Den Lodge
3.5 star property
The price is 11.203.969 ₫
13.444.763 ₫ total
includes taxes & fees
17 Jan - 18 Jan 2026
Sparrows Den Lodge
Garden
Pinewood Camping Pods - At Port Lympne Reserve

Camping in Hythe

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.4 out of 10, Exceptional, (30)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is 4.463.522 ₫
5.356.226 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Pinewood Camping Pods - At Port Lympne Reserve
Cottage | Private kitchen | Dishwasher, cookware/dishes/utensils
Rye House

Cottage in Rye

Rye House
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is 14.577.661 ₫
17.493.193 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Rye House
Interior
1-bedroom Apartment Sleeps 4, Parking

Apartment in Hythe

1-bedroom Apartment Sleeps 4, Parking
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is 3.870.238 ₫
4.644.285 ₫ total
includes taxes & fees
20 Dec - 21 Dec
1-bedroom Apartment Sleeps 4, Parking
Miscellaneous
Bexlet

Apartment in Bexhill-on-Sea

Bexlet
2.0 star property
8.6 out of 10, Excellent, (50)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is 2.318.269 ₫
2.782.064 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Bexlet
Deluxe Apartment | Free WiFi
Osborne Apartments

Aparthotel in Eastbourne

Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (90)
"great staff and facilities"
United Kingdom
Martin
Osborne Apartments
House, 1 Bedroom, Garden View | Garden
Calm Private Annex Ideal to Work, Rest & Explore

Apartment in Ashford

Calm Private Annex Ideal to Work, Rest & Explore
2.0 star property
The price is 2.815.318 ₫
3.378.382 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Calm Private Annex Ideal to Work, Rest & Explore
Cottage | Interior
Gun Hill Cottage

Cottage in Heathfield

Gun Hill Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
United Kingdom
Thomas
The price is 21.340.893 ₫
25.609.072 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Gun Hill Cottage
Cabin | 1 bedroom, iron/ironing board, free WiFi, bed sheets
Pet Friendly Private Cabin Town Eurotunnel Beach

Cabin in Hythe

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
8.0 out of 10, Very good, (3)
"The closeness to the High St. meant it was easy to walk to find something to eat/drink. The host was very helpful."
United Kingdom
David
The price is 2.167.251 ₫
2.600.702 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Pet Friendly Private Cabin Town Eurotunnel Beach
Cottage | Interior
Hakuna Matata

Cottage in Rye

Hakuna Matata
2.0 star property
8.8 out of 10, Excellent, (3)
"Well appointed and clean house. Convenient for shops and restaurants. Lovely beach a short walk away. Indian restaurant in Camber is great."
United Kingdom
Anonymous traveller
The price is 11.500.488 ₫
13.800.445 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hakuna Matata
House | Private kitchen | Fridge, microwave, oven, stovetop
Suspire House -sleeps6-garden-bbq-coastal Retreat

Residence in New Romney

Suspire House -sleeps6-garden-bbq-coastal Retreat
2.5 star property
The price is 5.000.671 ₫
7.691.173 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Suspire House -sleeps6-garden-bbq-coastal Retreat
Cottage | Interior
Amelia Cottage

Cottage in Battle

Amelia Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"Such a lovely cottage, well equipped and comfortable. Brilliant location for going out and about. We had an amazing stay and will be back again."
United Kingdom
Heather
The price is 11.559.651 ₫
13.871.581 ₫ total
includes taxes & fees
10 Jan - 11 Jan 2026
Amelia Cottage
Cabin | Children’s area
Big2vacation Exclusive Camber Sands Holiday Park

Chalet in Rye

Big2vacation Exclusive Camber Sands Holiday Park
3.0 star property
The price is 6.192.146 ₫
7.430.575 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Big2vacation Exclusive Camber Sands Holiday Park
Property grounds
Lilyrose Cottage

Cottage in Pevensey

Lilyrose Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
"All very good. However too many disabled parking spaces meaning too few for others"
United Kingdom
Graeme
The price is 12.863.699 ₫
15.436.580 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Lilyrose Cottage
Property grounds
Big2vacation2 Exclusive at new Beach Caravan Park

Cabin in Romney Marsh

Big2vacation2 Exclusive at new Beach Caravan Park
3.0 star property
The price is 4.953.717 ₫
5.944.461 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Big2vacation2 Exclusive at new Beach Caravan Park
Outdoor dining
Idyllic Studio in Tenterden

Apartment in Tenterden

Idyllic Studio in Tenterden
3.0 star property
The price is 3.715.288 ₫
4.458.346 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Idyllic Studio in Tenterden
Property grounds
Cozy Camber Caravan 3 Bedroom Retreat With Decking

Cabin in Rye

Cozy Camber Caravan 3 Bedroom Retreat With Decking
3.0 star property
4.0 out of 10, (2)
"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 4.086.816 ₫
5.847.616 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy Camber Caravan 3 Bedroom Retreat With Decking
Cottage | Interior
17 The Boathouse

Cottage in Rye

17 The Boathouse
3.0 star property
10.0 out of 10, Exceptional, (1)
"A lovely stay in a lovely property within walking distance of Rye town centre "
United Kingdom
Tony
The price is 11.915.332 ₫
14.298.398 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
17 The Boathouse
Cottage | Interior
7 Waves

Cottage in Rye

7 Waves
3.5 star property
8.0 out of 10, Very good, (1)
The price is 11.883.638 ₫
14.260.366 ₫ total
includes taxes & fees
22 Dec - 23 Dec
7 Waves
Exterior
16 The Boathouse

Cottage in Rye

16 The Boathouse
3.0 star property
9.2 out of 10, Wonderful, (5)
"It was an amazing stay great acommidation and close to the little town ."
United Kingdom
Andrew
The price is 11.404.700 ₫
13.685.640 ₫ total
includes taxes & fees
27 Dec - 28 Dec
16 The Boathouse
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchelsea Hotel Reviews

The Chatsworth Hotel

The Chatsworth Hotel

10/10 Excellent
"Clean room"
Kobika 2-night trip
Posted 2 days ago
The Chatsworth 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 6 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.