A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

Search Holiday Rentals in Winchelsea

  • 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

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchelsea holiday rentals

Cottage | Interior

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is ₹43,838
₹52,605 total
includes taxes & fees
12 Aug - 13 Aug
Sparrows Den Lodge
Interior

2. Summerhill Manor Retreat - 7 Bedroom House

Summerhill Manor Retreat - 7 Bedroom House
2.0 star property
Ashford
The price is ₹131,494
₹171,683 total
includes taxes & fees
7 Aug - 8 Aug
Summerhill Manor Retreat - 7 Bedroom House
The Hide Out | Living room

3. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (43 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 ₹18,798
₹18,798 total
includes taxes & fees
17 Aug - 18 Aug
Extraordinary Huts
Cottage | Interior

4. Rye House

Rye House
2.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
The price is ₹53,786
₹64,543 total
includes taxes & fees
16 Aug - 17 Aug
Rye House
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 ₹20,364
₹24,437 total
includes taxes & fees
4 Aug - 5 Aug
Oastbrook Glamping
View from property

6. Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (4 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is ₹8,042
₹9,651 total
includes taxes & fees
4 Aug - 5 Aug
Chestnut Meadow Camping
Deluxe Apartment | Free WiFi

7. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (128 reviews)
"Great location, appartment was very clean."
United Kingdom
Lisa
The price is ₹8,874
₹10,649 total
includes taxes & fees
10 Aug - 11 Aug
Osborne Apartments
Luxury Cabin | Living area | TV

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, (38 reviews)
"Great location we could see the lions from our room! Only slight downside was the sofa bed was a little on the uncomfortable side, but we had a great time and the staff were great too."
United Kingdom
Steve
The price is ₹19,580
₹23,496 total
includes taxes & fees
3 Sept - 4 Sept
Pinewood Camping Pods - At Port Lympne Reserve
Cottage | Balcony

9. 7 Waves

7 Waves
3.5 star property
Rye
8.0 out of 10, Very good, (1 review)
The price is ₹44,603
₹53,524 total
includes taxes & fees
13 Aug - 14 Aug
7 Waves
Fridge, microwave, oven, stovetop

10. Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Caravan - Sleeps 8 - Pets Ok - Parking - Patio
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 ₹14,759
₹21,190 total
includes taxes & fees
3 Sept - 4 Sept
Caravan - Sleeps 8 - Pets Ok - Parking - Patio
Miscellaneous

11. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (55 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is ₹9,539
₹11,447 total
includes taxes & fees
2 Sept - 3 Sept
Bexlet
Exterior

12. Church View

Church View
3.0 star property
Rye
6.0 out of 10, (1 review)
The price is ₹63,297
₹75,956 total
includes taxes & fees
18 Aug - 19 Aug
Church View
House | Living area | TV

13. Suspire House -sleeps6-garden-bbq-coastal Retreat

Suspire House -sleeps6-garden-bbq-coastal Retreat
3.0 star property
New Romney
2.0 out of 10, (1 review)
"We left after just 4 hours because the property was nothing like the listing. The photos give a far better impression than the reality. Before arrival, I had to chase the host for check-in instructions as nothing had been sent. Even after calling, I was only given the key safe code. Later that day, after we’d already left, I received an email stating there was a £100 charge per pet, despite the Hotels.com listing clearly advertising “pets go free.” The property appeared to have had only...
United Kingdom
Werner
The price is ₹17,624
₹27,322 total
includes taxes & fees
9 Aug - 10 Aug
Suspire House -sleeps6-garden-bbq-coastal Retreat
Fireplace

14. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is ₹53,786
₹64,543 total
includes taxes & fees
10 Aug - 11 Aug
1A Coastguard Cottages
2 bedrooms, free WiFi

15. Summerhill by Suspire

Summerhill by Suspire
2.5 star property
Ashford
The price is ₹14,394
₹23,446 total
includes taxes & fees
1 Sept - 2 Sept
Summerhill by Suspire
Cottage | Interior

16. Lantern Cottage

Lantern Cottage
3.5 star property
Rye
The price is ₹48,976
₹58,771 total
includes taxes & fees
13 Aug - 14 Aug
Lantern Cottage
Apartment | Balcony

17. 2-bed, Sleeps 4, Free Parking, Pets Allowed

2-bed, Sleeps 4, Free Parking, Pets Allowed
3.0 star property
Eastbourne City Centre
The price is ₹28,764
₹28,764 total
includes taxes & fees
1 Sept - 2 Sept
2-bed, Sleeps 4, Free Parking, Pets Allowed
Cottage | Living room

18. 3 Tidal

3 Tidal
3.5 star property
Rye
The price is ₹42,526
₹51,031 total
includes taxes & fees
11 Aug - 12 Aug
3 Tidal
Living area

19. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is ₹50,944
₹61,132 total
includes taxes & fees
1 Sept - 2 Sept
South Beach Landings 0028
Exterior

20. Hakuna Matata

Hakuna Matata
2.0 star property
Rye
8.8 out of 10, Excellent, (3 reviews)
"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 ₹55,754
₹66,905 total
includes taxes & fees
29 Aug - 30 Aug
Hakuna Matata
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

Cavendish Hotel

Cavendish Hotel

10/10 Excellent
"Great upgrade."
John 7-night trip
Posted 6 hours ago
Cavendish Hotel

Find out more about Winchelsea

Holiday Rentals in Winchelsea

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

  • View our selection of featured holiday rentals in Winchelsea
  • Use the map to find apartments and other holiday homes in the Winchelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchelsea while they last

Look no further and take a look at our great range of rental properties in Winchelsea!

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 14 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.