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

Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchelsea vacation 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 ￥71,067
￥85,281 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥31,801
￥31,801 total
includes taxes & fees
Nov 3 - Nov 4
Extraordinary Huts
A brick wall with a stone base, a wooden gate, and two planters with soil.

3. 3 Cinque Ports Street

3 Cinque Ports Street
3.0 star property
Rye
The price is ￥74,257
￥89,108 total
includes taxes & fees
Nov 5 - Nov 6
3 Cinque Ports Street
Interior

4. 3-bed Camber Sands Cabin - Pool - Parking - Pets

3-bed Camber Sands Cabin - Pool - Parking - Pets
3.0 star property
Rye
The price is ￥29,475
￥50,561 total
includes taxes & fees
Nov 8 - Nov 9
3-bed Camber Sands Cabin - Pool - Parking - Pets
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.

5. Osborne Apartments

Osborne Apartments
2.5 star property
Eastbourne
8.8 out of 10, Excellent, (155 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 ￥11,663
￥13,996 total
includes taxes & fees
Dec 2 - Dec 3
Osborne Apartments
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, (58 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is ￥13,196
￥15,835 total
includes taxes & fees
Nov 22 - Nov 23
Bexlet
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

7. 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 ￥13,193
￥15,831 total
includes taxes & fees
Dec 1 - Dec 2
Chestnut Meadow Camping
A cozy living room with a sofa, a white furry chair, a wooden table, and a fireplace.

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, (40 reviews)
"Wonderful experience and accommodation"
United Kingdom
Lesley
The price is ￥23,265
￥27,918 total
includes taxes & fees
Nov 11 - Nov 12
Pinewood Camping Pods - At Port Lympne Reserve
A row of white houses with brown roofs and a sandy beach in the foreground.

9. 16 The Boathouse

16 The Boathouse
3.0 star property
Rye
9.4 out of 10, Exceptional, (6 reviews)
"It was an amazing stay great acommidation and close to the little town ."
United Kingdom
Andrew
The price is ￥63,106
￥75,727 total
includes taxes & fees
Nov 5 - Nov 6
16 The Boathouse
A compact kitchen with a stove, oven, sink, and wooden countertops.

10. 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 ￥19,548
￥30,097 total
includes taxes & fees
Nov 10 - Nov 11
Caravan With Decking&patio-8/10 Berth-pet Friendly
A row of white houses with red roofs by a calm water body, boats docked, and a red sign in the foreground.

11. 17 The Boathouse

17 The Boathouse
3.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
"A lovely stay in a lovely property within walking distance of Rye town centre "
United Kingdom
Tony
The price is ￥64,883
￥77,860 total
includes taxes & fees
Nov 7 - Nov 8
17 The Boathouse
Living area

12. Cabin - Sleeps 8 - Garden and Parking

Cabin - Sleeps 8 - Garden and Parking
3.0 star property
St Leonards-On-Sea
The price is ￥33,367
￥43,839 total
includes taxes & fees
Nov 3 - Nov 4
Cabin - Sleeps 8 - Garden and Parking
A cozy living room with a sofa, a dining table set for two, and a small side table.

13. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is ￥96,882
￥116,258 total
includes taxes & fees
Nov 6 - Nov 7
1A Coastguard Cottages
A living room with a sofa, coffee table, and a fireplace.

14. 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 ￥29,659
￥45,718 total
includes taxes & fees
Nov 3 - Nov 4
Suspire House -sleeps6-garden-bbq-coastal Retreat
A narrow cobblestone path flanked by a brick house with a black metal fence, leading to a tree-lined street.

15. Lantern Cottage

Lantern Cottage
3.5 star property
Rye
The price is ￥79,396
￥95,274 total
includes taxes & fees
Nov 7 - Nov 8
Lantern Cottage
A wooden cabin room with a bed, a TV mounted on the wall, and a door leading outside.

16. 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 ￥13,107
￥15,728 total
includes taxes & fees
Nov 4 - Nov 5
Pet Friendly Private Cabin Town Eurotunnel Beach
A bedroom with a bed, bedside table, nightstand, and a ceiling light fixture.

17. Summerhill by Suspire

Summerhill by Suspire
3.0 star property
Ashford
The price is ￥29,845
￥45,941 total
includes taxes & fees
Nov 3 - Nov 4
Summerhill by Suspire
A bench overlooking a coastal view with a clear sky and a distant shoreline.

18. 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 ￥54,499
￥54,499 total
includes taxes & fees
Nov 3 - Nov 4
2-bed, Sleeps 4, Free Parking, Pets Allowed
A cozy room with a brick fireplace, blue sofas, a wooden coffee table, and a guitar.

19. Summerhill Manor Retreat - 7 Bedroom House

Summerhill Manor Retreat - 7 Bedroom House
2.0 star property
Ashford
The price is ￥222,447
￥289,722 total
includes taxes & fees
Nov 3 - Nov 4
Summerhill Manor Retreat - 7 Bedroom House
A wooden deck with a striped cushion, a brick wall, and a view of a river.

20. 7 Waves

7 Waves
3.5 star property
Rye
8.0 out of 10, Very good, (1 review)
The price is ￥72,307
￥86,768 total
includes taxes & fees
Nov 7 - Nov 8
7 Waves
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

Holiday Inn Ashford Central by IHG

Holiday Inn Ashford Central by IHG

10/10 Excellent
"Excellent"
Lee 1-night trip
Posted 2 days ago
Holiday Inn Ashford Central by IHG

Find out more about Winchelsea

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

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Frequently asked questions

Can I find vacation rentals in Winchelsea?

Yes, we have vacation rentals near well known local attractions in Winchelsea, or you can select a more secluded option if you're looking for relaxation. Our travelers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What's the top vacation rental that Winchelsea has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This vacation home rental near 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 vacation with a garden and a hot tub.

How many vacation rentals are there in Winchelsea?

With 14 Expedia vacation rentals, you're sure 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 vacation rental in Winchelsea like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchelsea. Vacation rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.