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Winchelsea Beach Vacation Rentals

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Our top choices for Winchelsea Beach vacation rentals

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 CA $135
CA $411 total
includes taxes & fees
Sep 20 - Sep 21
White Haven - with 2 double rooms

2. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is CA $637
CA $764 total
includes taxes & fees
Oct 5 - Oct 6
Sparrows Den Lodge

3. 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 CA $586
CA $586 total
includes taxes & fees
Sep 30 - Oct 1
1 bedroom accommodation in Winchelsea Beach, near Rye

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 CA $271
CA $271 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $215
CA $264 total
includes taxes & fees
Sep 20 - Sep 21
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

6. Hillside retreat - 2 bedrooms sleeps 6

Hillside retreat - 2 bedrooms sleeps 6
Hastings
The price is CA $135
CA $411 total
includes taxes & fees
Sep 20 - Sep 21
Hillside retreat - 2 bedrooms sleeps 6

7. 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 CA $190
CA $283 total
includes taxes & fees
Oct 20 - Oct 21
Caravan With Decking&patio-8/10 Berth-pet Friendly

8. 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 CA $117
CA $140 total
includes taxes & fees
Sep 20 - Sep 21
Chestnut Meadow Camping

9. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is CA $782
CA $938 total
includes taxes & fees
Oct 4 - Oct 5
1A Coastguard Cottages

10. 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 CA $304
CA $327 total
includes taxes & fees
Oct 18 - Oct 19
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

11. 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 CA $474
CA $474 total
includes taxes & fees
Oct 15 - Oct 16
An unusual two-storey apartment with beams and an open fire.

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 CA $243
CA $363 total
includes taxes & fees
Sep 29 - Sep 30
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

13. 2 bedroom accommodation in Rye

2 bedroom accommodation in Rye
Rye
9.8 out of 10, Exceptional, (6 reviews)
"Very comfortable accommodation and so central to shops and restaurants. Particularly loved the wood burning stove."
United States
Sheila Davies
The price is CA $435
CA $435 total
includes taxes & fees
Sep 20 - Sep 21
2 bedroom accommodation in Rye

14. Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (56 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
The price is CA $123
CA $148 total
includes taxes & fees
Oct 13 - Oct 14
Bexlet

15. 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 CA $140
CA $624 total
includes taxes & fees
Oct 8 - Oct 9
Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

16. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
Camber
The price is CA $347
CA $396 total
includes taxes & fees
Oct 5 - Oct 6
Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

17. Cabin - Sleeps 8 - Garden and Parking

Cabin - Sleeps 8 - Garden and Parking
3.0 star property
St Leonards-On-Sea
The price is CA $226
CA $305 total
includes taxes & fees
Oct 15 - Oct 16
Cabin - Sleeps 8 - Garden and Parking

18. 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 CA $157
CA $434 total
includes taxes & fees
Sep 30 - Oct 1
Rhodown - sun on the terrace all round

19. 3 Tidal

3 Tidal
3.5 star property
Rye
The price is CA $618
CA $742 total
includes taxes & fees
Sep 24 - Sep 25
3 Tidal

20. 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 traveller
The price is CA $380
CA $380 total
includes taxes & fees
Sep 30 - Oct 1
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchelsea Beach. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

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 High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach 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.