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Winchelsea Beach Vacation Rentals

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Our top choices for Winchelsea Beach vacation rentals

1. Grogu's Rest - 2 bedrooms with decking sleeps 6

Grogu's Rest - 2 bedrooms with decking sleeps 6
Winchelsea Beach
8.8 out of 10, Excellent, (8 reviews)
"great stay again"
United Kingdom
lindsay r.
The price is ¥20,733
¥52,697 total
includes taxes & fees
Aug 22 - Aug 23
Grogu's Rest - 2 bedrooms with decking sleeps 6

2. 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 ¥15,550
¥47,514 total
includes taxes & fees
Sep 1 - Sep 2
White Haven - with 2 double rooms

3. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is ¥73,613
¥88,336 total
includes taxes & fees
Aug 31 - Sep 1
Sparrows Den Lodge

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 ¥32,552
¥32,552 total
includes taxes & fees
Aug 20 - Aug 21
Extraordinary Huts

5. 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 ¥24,880
¥30,927 total
includes taxes & fees
Aug 20 - Aug 21
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

6. 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 ¥13,501
¥16,201 total
includes taxes & fees
Sep 13 - Sep 14
Chestnut Meadow Camping

7. 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 ¥26,248
¥37,046 total
includes taxes & fees
Sep 1 - Sep 2
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

8. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is ¥90,289
¥108,347 total
includes taxes & fees
Sep 3 - Sep 4
1A Coastguard Cottages

9. Hillside retreat - 2 bedrooms sleeps 5

Hillside retreat - 2 bedrooms sleeps 5
Hastings
The price is ¥15,550
¥47,514 total
includes taxes & fees
Sep 1 - Sep 2
Hillside retreat - 2 bedrooms sleeps 5

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 ¥50,305
¥50,305 total
includes taxes & fees
Sep 6 - Sep 7
An unusual two-storey apartment with beams and an open fire.

11. 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 ¥39,954
¥45,569 total
includes taxes & fees
Sep 3 - Sep 4
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

12. 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 ¥28,076
¥41,034 total
includes taxes & fees
Sep 6 - Sep 7
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

13. 2 bedroom accommodation in Rye

2 bedroom accommodation in Rye
Rye
9.6 out of 10, Exceptional, (5 reviews)
"Very comfortable accommodation and so central to shops and restaurants. Particularly loved the wood burning stove."
United States
Sheila Davies
The price is ¥55,504
¥55,504 total
includes taxes & fees
Aug 27 - Aug 28
2 bedroom accommodation in Rye

14. 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 ¥16,018
¥19,221 total
includes taxes & fees
Sep 2 - Sep 3
Bexlet

15. Bluebell corner - with small enclosed decking

Bluebell corner - with small enclosed decking
Hastings
The price is ¥15,550
¥47,514 total
includes taxes & fees
Sep 2 - Sep 3
Bluebell corner - with small enclosed decking

16. The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Had a great time, thank you very much ! Would definitely stay again! Good location, easy to get into Rye and surounds."
United States
Anonymous traveler
The price is ¥43,882
¥43,882 total
includes taxes & fees
Aug 20 - Aug 21
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

17. Fir Tree - 2 bedrooms sleeps 5

Fir Tree - 2 bedrooms sleeps 5
Hastings
The price is ¥23,325
¥55,289 total
includes taxes & fees
Aug 20 - Aug 21
Fir Tree - 2 bedrooms sleeps 5

18. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is ¥85,546
¥102,655 total
includes taxes & fees
Sep 1 - Sep 2
South Beach Landings 0028

19. Rhodown - sun on the terrace all round

Rhodown - sun on the terrace all round
Hastings
9.0 out of 10, Wonderful, (6 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 ¥18,136
¥50,089 total
includes taxes & fees
Sep 3 - Sep 4
Rhodown - sun on the terrace all round

20. Monument - 2 bedrooms sleeps 4

Monument - 2 bedrooms sleeps 4
Hastings
The price is ¥18,141
¥50,105 total
includes taxes & fees
Sep 6 - Sep 7
Monument - 2 bedrooms sleeps 4
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

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:

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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?

Converted barn / Oast House with amazing views and EV chargers: This vacation home rental near Winchelsea Beach is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.