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Holiday Rentals in Winchelsea Beach

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchelsea Beach holiday 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 €259
includes taxes & fees
4 Oct - 5 Oct
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 €356
includes taxes & fees
15 Oct - 16 Oct
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 €481
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.

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 €179
includes taxes & fees
5 Oct - 6 Oct
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 €88
includes taxes & fees
4 Oct - 5 Oct
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 €138
includes taxes & fees
6 Oct - 7 Oct
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 €171
includes taxes & fees
7 Oct - 8 Oct
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 €93
includes taxes & fees
13 Oct - 14 Oct
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 €258
includes taxes & fees
7 Oct - 8 Oct
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 €298
includes taxes & fees
15 Oct - 16 Oct
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 €366
includes taxes & fees
8 Oct - 9 Oct
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 €157
includes taxes & fees
4 Oct - 5 Oct
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 €193
includes taxes & fees
1 Nov - 2 Nov
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 €503
includes taxes & fees
7 Oct - 8 Oct
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 €273
includes taxes & fees
4 Oct - 5 Oct
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 €184
includes taxes & fees
5 Oct - 6 Oct
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 €208
includes taxes & fees
2 Nov - 3 Nov
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
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 €117
includes taxes & fees
12 Oct - 13 Oct
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 €316
includes taxes & fees
4 Oct - 5 Oct
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

The Relais Cooden Beach

The Relais Cooden Beach

10/10 Excellent
"Great stay"
Jordanna 1-night trip
Posted 1 hour ago
The Relais Cooden Beach

Find out more about Winchelsea Beach

Everything you need to know about Winchelsea Beach 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 Beach 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 Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchelsea Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchelsea Beach. 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 Beach 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 Beach holiday rentals we have selected for you start as low as €88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchelsea Beach rentals

At Expedia, we put the best Winchelsea Beach 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 Beach 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 Beach 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 Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winchelsea Beach?

Yes, there are holiday rentals close to the most popular sights in Winchelsea Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchelsea Beach has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This holiday home rental outside of 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 holiday with a garden and 1 hot tub.

How many holiday rentals are there in Winchelsea Beach?

With 9 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Winchelsea Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchelsea Beach. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.