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

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Our top choices for Winchelsea holiday rentals

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is £409
includes taxes & fees
31 Aug - 1 Sept
Sparrows Den Lodge

2. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (45 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 £145
includes taxes & fees
10 Sept - 11 Sept
Extraordinary Huts

3. 7 Waves

7 Waves
3.5 star property
Rye
8.0 out of 10, Very good, (1 review)
The price is £416
includes taxes & fees
28 Aug - 29 Aug
7 Waves

4. 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 £86
includes taxes & fees
30 Aug - 31 Aug
Bexlet

5. Chestnut Meadow Camping

Chestnut Meadow Camping
4.0 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 £75
includes taxes & fees
3 Sept - 4 Sept
Chestnut Meadow Camping

6. 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 £172
includes taxes & fees
1 Sept - 2 Sept
Caravan With Decking&patio-8/10 Berth-pet Friendly

7. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (143 reviews)
"Very clean and welcoming, Staff are always polite friendly and approachable."
United Kingdom
Paul
The price is £83
includes taxes & fees
3 Sept - 4 Sept
Osborne Apartments

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)
"Wonderful experience and accommodation"
United Kingdom
Lesley
The price is £215
includes taxes & fees
15 Sept - 16 Sept
Pinewood Camping Pods - At Port Lympne Reserve

9. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is £427
includes taxes & fees
31 Aug - 1 Sept
3 Cinque Ports Street

10. 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 £190
includes taxes & fees
26 Aug - 27 Aug
Oastbrook Glamping

11. 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 £203
includes taxes & fees
3 Sept - 4 Sept
Suspire House -sleeps6-garden-bbq-coastal Retreat

12. 3 Tidal

3 Tidal
3.5 star property
Rye
The price is £397
includes taxes & fees
4 Sept - 5 Sept
3 Tidal

13. Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
Hythe
8.0 out of 10, Very good, (3 reviews)
"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 £74
includes taxes & fees
12 Sept - 13 Sept
Pet Friendly Private Cabin Town Eurotunnel Beach

14. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is £475
includes taxes & fees
1 Sept - 2 Sept
South Beach Landings 0028

15. 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 £224
includes taxes & fees
1 Sept - 2 Sept
2-bed, Sleeps 4, Free Parking, Pets Allowed

16. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is £502
includes taxes & fees
3 Sept - 4 Sept
1A Coastguard Cottages

17. Summerhill Manor Retreat - 7 Bedroom House

Summerhill Manor Retreat - 7 Bedroom House
2.0 star property
Ashford
The price is £1,297
includes taxes & fees
30 Aug - 31 Aug
Summerhill Manor Retreat - 7 Bedroom House

18. The Boathouse

The Boathouse
3.0 star property
St Leonards-On-Sea
10.0 out of 10, Exceptional, (1 review)
The price is £425
includes taxes & fees
4 Sept - 5 Sept
The Boathouse

19. Summerhill by Suspire

Summerhill by Suspire
2.5 star property
Ashford
The price is £175
includes taxes & fees
1 Sept - 2 Sept
Summerhill by Suspire

20. Luxury Kent Bungalow Retreat Sleeps 12

Luxury Kent Bungalow Retreat Sleeps 12
4.0 star property
Tonbridge
Luxury Kent Bungalow Retreat Sleeps 12
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

Find out more about Winchelsea

Everything you need to know about Winchelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchelsea holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchelsea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchelsea holiday rentals we have selected for you start as low as £44 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchelsea rentals

At Expedia, we put the best Winchelsea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchelsea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchelsea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchelsea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

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.

What are some of the best holiday rentals that Winchelsea has to offer?

Converted barn / Oast House with amazing views and EV chargers: This holiday home rental outside of Winchelsea is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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 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.