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Winchelsea Beach Vacation Rentals

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Check prices for these dates

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

Our top choices for Winchelsea Beach vacation rentals

A mobile home with a white exterior, a covered porch, and a number 27 sign.

1. White Haven - with 2 double rooms

White Haven - with 2 double rooms
Winchelsea Beach
2.0 out of 10, (1 review)
"Check in was easy and location was good, thise are the only positives. The property is extremely dated and dirty. The furnishings in communal areas were torn, threadbare, stained, dirty and smelly. The carpets were dirty, covered in dog and human hair. There was mould above the shower and dirt and mould under the sink. The areas around the toilets were soiled with rusted old urine splashes. There was mould on one of the bedroom walls.The kitchen cupboard fascias were peeling and the handles all...
United Kingdom
Emma V.
The price is ￥15,049
￥45,984 total
includes taxes & fees
Oct 6 - Oct 7
White Haven - with 2 double rooms
A brick house with a small patio, a white door, and a wooden fence.

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (12 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
The price is ￥63,293
￥63,293 total
includes taxes & fees
Oct 15 - Oct 16
1 bedroom accommodation in Winchelsea Beach, near Rye
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

3. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is ￥71,244
￥85,493 total
includes taxes & fees
Oct 9 - Oct 10
Sparrows Den Lodge
A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

4. 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 ￥30,550
￥30,550 total
includes taxes & fees
Nov 5 - Nov 6
Extraordinary Huts
A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

5. 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 ￥13,071
￥15,685 total
includes taxes & fees
Oct 6 - Oct 7
Chestnut Meadow Camping
A bedroom with a bed, a chair, a wooden table, and a potted plant.

6. 1 Bed - Sleeps 2 - Near Beach - Parking

1 Bed - Sleeps 2 - Near Beach - Parking
3.5 star property
Hastings
The price is ￥20,405
￥24,486 total
includes taxes & fees
Oct 22 - Oct 23
1 Bed - Sleeps 2 - Near Beach - Parking
A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

7. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
10.0 out of 10, Exceptional, (13 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
The price is ￥24,079
￥29,931 total
includes taxes & fees
Oct 6 - Oct 7
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
A modern building with a curved facade, multiple balconies, and a grassy area in front.

8. 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 ￥13,760
￥16,513 total
includes taxes & fees
Oct 13 - Oct 14
Bexlet
A riverside view with a wooden dock, lush greenery, and a calm water body.

9. Hillside retreat - 2 bedrooms sleeps 6

Hillside retreat - 2 bedrooms sleeps 6
Hastings
The price is ￥15,049
￥45,984 total
includes taxes & fees
Oct 12 - Oct 13
Hillside retreat - 2 bedrooms sleeps 6
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

10. An unusual two-storey apartment with beams and an open fire.

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
The price is ￥41,822
￥41,822 total
includes taxes & fees
Oct 31 - Nov 1
An unusual two-storey apartment with beams and an open fire.
A room with a fireplace, a desk, a chair, and a large window with a view of greenery.

11. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds
Hastings
8.0 out of 10, Very good, (5 reviews)
"We had a very pleasant stay at this spacious and comfortable home, which was well-suited for our larger group. The garden was a particular highlight, offering ample space and the added delight of fresh fruit to pick. The location is great, being within a short walking distance of the beach and sea (20mins). The property was generally tidy, there were a few spiderwebs which luckily didn't have any spiders. If these were removed it would enhance the experience. Parking proved somewhat challenging...
United Kingdom
Tabassum A.
The price is ￥10,116
￥63,624 total
includes taxes & fees
Oct 8 - Oct 9
Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds
A wooden balcony attached to a building with a large tree in the background.

12. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
Rye
10.0 out of 10, Exceptional, (2 reviews)
"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."
United Kingdom
Kerry H.
The price is ￥23,828
￥27,172 total
includes taxes & fees
Oct 6 - Oct 7
A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye
A river with a boat, surrounded by greenery and buildings.

13. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
Hastings
9.4 out of 10, Exceptional, (3 reviews)
"Excellent"
United Kingdom
Melanie G.
The price is ￥20,902
￥33,443 total
includes taxes & fees
Nov 1 - Nov 2
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms
A dining area with a green staircase, a glass table, and chairs.

14. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is ￥74,442
￥89,330 total
includes taxes & fees
Oct 9 - Oct 10
3 Cinque Ports Street
A modern living room with a grey sofa, a wooden coffee table, a TV on a stand, and light blue curtains.

15. Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.0 out of 10, Wonderful, (7 reviews)
"Lovely peaceful setting and the caravan had everything you would need and bonus being so close to Hastings"
United Kingdom
William E.
The price is ￥17,557
￥48,492 total
includes taxes & fees
Oct 6 - Oct 7
Rhodown - sun on the terrace all round
A compact kitchen with a stove, oven, sink, and wooden countertops.

16. 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 ￥20,702
￥31,153 total
includes taxes & fees
Oct 8 - Oct 9
Caravan With Decking&patio-8/10 Berth-pet Friendly
A modern living room with a sofa, a coffee table, and a dining area with a table set for four.

17. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
Camber Rye
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful caravan. We went at Easter 2026 and there were beautiful Easter touches bunnies etc throughout the caravan. Chocolates and Proscecco were a lovely touch. Checking in process was seamless and they provided so much helpful information. Would recommend and will definitely be back for another stay. Dog friendly too, my dogs loved the warm cozy throws provided and enclosed gated decking area"
United Kingdom
Claire O.
The price is ￥32,816
￥37,205 total
includes taxes & fees
Nov 1 - Nov 2
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking
A rustic wooden structure with a kitchen area, a bench, and a trash bin.

18. Damson Hut at The Secret Garden

Damson Hut at The Secret Garden
Biddenden
The price is ￥16,984
￥20,182 total
includes taxes & fees
Oct 6 - Oct 7
Damson Hut at The Secret Garden
A room with a four-poster bed, wooden walls, a window, and string lights.

19. Tree House at The Secret Garden

Tree House at The Secret Garden
Biddenden
The price is ￥16,984
￥20,182 total
includes taxes & fees
Oct 6 - Oct 7
Tree House at The Secret Garden
A living room with a sectional sofa, a fireplace, and a TV mounted on the wall.

20. The Pigsty at the Secret Garden

The Pigsty at the Secret Garden
2.0 star property
Ashford
The price is ￥45,127
￥54,152 total
includes taxes & fees
Oct 11 - Oct 12
The Pigsty at the Secret Garden
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 Beach Hotel Reviews

Flackley Ash Country House Hotel

Flackley Ash Country House Hotel

10/10 Excellent
"Lovely clean little hotel"
Sandra 1-night trip
Posted 12 hours ago
Flackley Ash Country House Hotel

Find out more about Winchelsea Beach

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

  • View our selection of featured holiday rentals in Winchelsea Beach
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Look no further and take a look at our great range of rental properties in Winchelsea Beach!

Frequently asked questions

Are there vacation rentals in Winchelsea Beach?

Yes, you can find vacation rentals close to popular local attractions in Winchelsea Beach, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Winchelsea Beach?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This vacation home rental near Winchelsea Beach 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 Beach?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Winchelsea Beach stay.

What can I see and do in Winchelsea Beach?

Winchelsea Beach and Pett Level Beach are a couple of lovely local spots to get outside and enjoy nature. High Weald and Rye Harbour Nature Reserve are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchelsea Beach?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchelsea Beach. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for families.