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

Our top choices for Winchelsea holiday rentals

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
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
5 Jan - 6 Jan 2026
Pinewood Camping Pods - At Port Lympne Reserve
The Hide Out | Living room
Extraordinary Huts

Cabin in Rye

Extraordinary Huts
3.0 star property
9.6 out of 10, Exceptional, (41)
"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
Extraordinary Huts
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
30 Dec - 31 Dec
1-bedroom Apartment Sleeps 4, Parking
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
15 Jan - 16 Jan 2026
Big2vacation2 Exclusive at new Beach Caravan Park
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
1 Jan - 2 Jan 2026
Big2vacation Exclusive Camber Sands Holiday Park
Miscellaneous
Grace Apartments - Living Stone 2

Apartment in Ashford

Grace Apartments - Living Stone 2
2.0 star property
Grace Apartments - Living Stone 2
Apartment | 1 bedroom, free WiFi, bed sheets
Tranquil Loft Apartment Overlooking Countryside

Apartment in Hailsham

Tranquil Loft Apartment Overlooking Countryside
3.0 star property
10.0 out of 10, Exceptional, (1)
Tranquil Loft Apartment Overlooking Countryside
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
15 Jan - 16 Jan 2026
Gun Hill Cottage
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
14 Jan - 15 Jan 2026
Bexlet
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 4.289.767 ₫
6.057.722 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy Camber Caravan 3 Bedroom Retreat With Decking
Books
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 2.820.139 ₫
3.384.167 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Calm Private Annex Ideal to Work, Rest & Explore
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 12.915.975 ₫
15.499.311 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Lilyrose Cottage
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 11.547.224 ₫
13.856.527 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hakuna Matata
Fridge, electric kettle, toaster, cookware/dishes/utensils
The Boathouse

Cottage in St Leonards-On-Sea

The Boathouse
3.0 star property
10.0 out of 10, Exceptional, (1)
The Boathouse
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 5.020.993 ₫
7.722.429 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Suspire House -sleeps6-garden-bbq-coastal Retreat
Apartment | Balcony
Charming 1-bedroom Apartment Near South Downs

Apartment in Hailsham

Charming 1-bedroom Apartment Near South Downs
3.0 star property
9.8 out of 10, Exceptional, (9)
"Everything we needed, just like home from home and in a lovely quiet location"
United Kingdom
Brenda
Charming 1-bedroom Apartment Near South Downs
Luxury Cabin, Accessible, Ensuite (Avalon Waterside Lodge) | Exterior
Oastbrook Estate Vineyard

Holiday Home in Robertsbridge

Oastbrook Estate Vineyard
3.5 star property
10.0 out of 10, Exceptional, (2)
"We had the most wonderful time staying at the Hobbit Hole. The property was incredible: well looked after and very clean. Everything has been very well thought out. We thoroughly enjoyed gazing at the scenery out the window and enjoying the peaceful area."
United Kingdom
Kathryn
Oastbrook Estate Vineyard
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 11.606.627 ₫
13.927.952 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Amelia Cottage
Miscellaneous
Grace Apartments - Living Rock

Apartment in Ashford

Grace Apartments - Living Rock
3.5 star property
4.8 out of 10, (5)
"I needed immediate help when the sat sav dumped me nearby & my host talked me all the way to the front door which was a huge relief. The accommodation is dated but I knew that from the photos it was very clean though & i was surprised to find all the essentials had ben left. I wasn’t expecting that so had brought it all with me. The bed was very comfortable, the shower was lovely & the washing machine was handy. The area was very noisy though as it is right in town above a bar & I was there at...
United Kingdom
Rachel
Grace Apartments - Living Rock
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 1 day 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.