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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchelsea holiday rentals

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is £409
includes taxes & fees
18 Oct - 19 Oct
Sparrows Den Lodge
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

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 £136
includes taxes & fees
12 Oct - 13 Oct
Extraordinary Huts
A dining area with a green staircase, a glass table, and chairs.

3. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is £427
includes taxes & fees
17 Oct - 18 Oct
3 Cinque Ports Street
A hotel room with a bed, two armchairs, a small round table with a vase of flowers, and a view of the outdoors through large windows with curtains.

4. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (154 reviews)
"Very spacious apartment with everything you require to make your stay comfortable. Have booked to return again several times this year. Great for someone working away for several days"
United Kingdom
Melvyn Spencer
The price is £73
includes taxes & fees
8 Nov - 9 Nov
Osborne Apartments
A compact kitchen with a stove, oven, sink, and wooden countertops.

5. 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 £145
includes taxes & fees
18 Oct - 19 Oct
Caravan With Decking&patio-8/10 Berth-pet Friendly
A modern building with a curved facade, multiple balconies, and a grassy area in front.

6. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (57 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is £72
includes taxes & fees
13 Oct - 14 Oct
Bexlet
A cozy living room with a sofa, a white furry chair, a wooden table, and a fireplace.

7. 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, (40 reviews)
"Wonderful experience and accommodation"
United Kingdom
Lesley
The price is £147
includes taxes & fees
4 Nov - 5 Nov
Pinewood Camping Pods - At Port Lympne Reserve
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

8. Chestnut Meadow Camping

Chestnut Meadow Camping
4.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (5 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is £83
includes taxes & fees
11 Oct - 12 Oct
Chestnut Meadow Camping
A living room with a sectional sofa, a fireplace, and a TV mounted on the wall.

9. The Pigsty at the Secret Garden

The Pigsty at the Secret Garden
2.0 star property
Ashford
The price is £245
includes taxes & fees
12 Oct - 13 Oct
The Pigsty at the Secret Garden
A row of white houses with red roofs by a calm water body, boats docked, and a red sign in the foreground.

10. 17 The Boathouse

17 The Boathouse
3.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
The price is £410
includes taxes & fees
30 Oct - 31 Oct
17 The Boathouse
A bedroom with a bed, a chair, a wooden table, and a potted plant.

11. 1 Bed - Sleeps 2 - Near Beach - Parking

1 Bed - Sleeps 2 - Near Beach - Parking
3.5 star property
Hastings
The price is £117
includes taxes & fees
22 Oct - 23 Oct
1 Bed - Sleeps 2 - Near Beach - Parking
A dining area with a table, chairs, a bottle of champagne, and a view through a glass door.

12. 3 Tidal

3 Tidal
3.5 star property
Rye
The price is £397
includes taxes & fees
27 Oct - 28 Oct
3 Tidal
Exterior detail

13. Cabin - Sleeps 8 - Garden and Parking

Cabin - Sleeps 8 - Garden and Parking
3.0 star property
St Leonards-On-Sea
The price is £204
includes taxes & fees
3 Nov - 4 Nov
Cabin - Sleeps 8 - Garden and Parking
A cozy living room with a sofa, a dining table set for two, and a small side table.

14. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is £502
includes taxes & fees
12 Oct - 13 Oct
1A Coastguard Cottages
A living room with a sofa, coffee table, and a fireplace.

15. 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 £201
includes taxes & fees
30 Oct - 31 Oct
Suspire House -sleeps6-garden-bbq-coastal Retreat
A wooden deck with a striped cushion, a brick wall, and a view of a river.

16. 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
12 Oct - 13 Oct
7 Waves
A narrow cobblestone path flanked by a brick house with a black metal fence, leading to a tree-lined street.

17. Lantern Cottage

Lantern Cottage
3.5 star property
Rye
The price is £457
includes taxes & fees
2 Nov - 3 Nov
Lantern Cottage
A view through a window with hanging fish decorations.

18. Rye House

Rye House
2.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
The price is £502
includes taxes & fees
26 Oct - 27 Oct
Rye House
A white two-story house with a blue door and a white picket fence.

19. 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 £407
includes taxes & fees
17 Oct - 18 Oct
Hakuna Matata
A living room with a grey sofa, a black ottoman, and a yellow throw pillow. There are large sliding glass doors leading to a balcony with a view of houses and a fence.

20. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is £475
includes taxes & fees
31 Oct - 1 Nov
South Beach Landings 0028
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 Chatsworth Hotel

The Chatsworth Hotel

8/10 Good
"A Beautiful Hotel with Real Character — Just a Few Details to Fix We thoroughly enjoyed our stay at this beautiful hotel, which has a charm all of its own — not least the classic birdcage lift, a functioning showpiece that we never tired of seeing. Our room was pleasant and full of character, with lovely high ceilings, and the bathroom was truly spectacular — both in size and in the quality of its amenities. Breakfast was enjoyable too, with a good variety and quality on offer. The real highlight for us, though, was the piano bar: we loved relaxing over pre-dinner drinks while listening to a talented singer and piano player. A wonderful way to start the evening. That said, there were a few areas that let the experience down. General upkeep in the bedrooms could be better — our net curtain had a large tear, which we felt was unacceptable for a hotel of this standard. We also noticed a build-up of dust around the coffee area, and housekeeping in general would benefit from closer attention to detail. The good news is that these issues should be easy to address. Overall, with the upkeep and housekeeping improved as a priority — and a few extra touches such as an in-room mini fridge and safe — this hotel would be truly fabulous. We'd happily return."
Onkar 2-night trip
Posted 5 hours ago
The Chatsworth Hotel

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 £33 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?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This holiday home rental outside of Winchelsea offers an indoor pool, a patio and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your holiday with a garden and 1 hot tub.

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.