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Winchelsea Beach Vacation Rentals

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Our top choices for Winchelsea Beach vacation rentals

1. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is CA $644
CA $773 total
includes taxes & fees
Aug 12 - Aug 13
Sparrows Den Lodge

2. 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 CA $159
CA $439 total
includes taxes & fees
Sep 1 - Sep 2
Grogu's Rest - 2 bedrooms with decking sleeps 6

3. 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 $136
CA $416 total
includes taxes & fees
Sep 1 - Sep 2
White Haven - with 2 double rooms

4. Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (43 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 $276
CA $276 total
includes taxes & fees
Aug 17 - Aug 18
Extraordinary Huts

5. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is CA $791
CA $949 total
includes taxes & fees
Aug 6 - Aug 7
1A Coastguard Cottages

6. RYE HOUSE: Central Location & WiFi

RYE HOUSE: Central Location & WiFi
Rye
10.0 out of 10, Exceptional, (1 review)
"The owner made a great effort to decorate the place for xmas. There was a good welcome pack and the place was well equiped. Very comfortable accommodation.....thoroughly enjoyed our week at xmas."
United Kingdom
Alan P.
The price is CA $977
CA $977 total
includes taxes & fees
Aug 16 - Aug 17
RYE HOUSE: Central Location & WiFi

7. 1A Coastguard Cottages, Rye Harbour

1A Coastguard Cottages, Rye Harbour
Rye
The price is CA $1,023
CA $1,023 total
includes taxes & fees
Aug 6 - Aug 7
1A Coastguard Cottages, Rye Harbour

8. 4 bedroom accommodation in Pett

4 bedroom accommodation in Pett
Pett
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful one night stay at Holly Cottage with family. Location is great with pubs and tearoom close by. We all commented on how comfortable the beds were and how quiet the cottage is. Would definitely recommend!"
United States
Sarah Gunner
The price is CA $958
CA $958 total
includes taxes & fees
Aug 31 - Sep 1
4 bedroom accommodation in Pett

9. 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 CA $486
CA $486 total
includes taxes & fees
Aug 27 - Aug 28
2 bedroom accommodation in Rye

10. 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 $170
CA $219 total
includes taxes & fees
Aug 4 - Aug 5
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

11. Charming 3-bedroom house in soothing Playden Rye neighborhood

Charming 3-bedroom house in soothing Playden Rye neighborhood
Playden, Rye
10.0 out of 10, Exceptional, (1 review)
"Beautiful house and garden near Rye"
United States
Edward W.
The price is CA $454
CA $561 total
includes taxes & fees
Aug 9 - Aug 10
Charming 3-bedroom house in soothing Playden Rye neighborhood

12. Willow Cottage: A Cozy Escape

Willow Cottage: A Cozy Escape
Rye
The price is CA $1,668
CA $1,668 total
includes taxes & fees
Aug 31 - Sep 1
Willow Cottage: A Cozy Escape

13. Oastbrook Glamping

Oastbrook Glamping
2.0 star property
Robertsbridge
10.0 out of 10, Exceptional, (1 review)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
United Kingdom
Sima
The price is CA $299
CA $359 total
includes taxes & fees
Aug 3 - Aug 4
Oastbrook Glamping

14. 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 CA $210
CA $305 total
includes taxes & fees
Sep 2 - Sep 3
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

15. 7 Waves

7 Waves
3.5 star property
Rye
8.0 out of 10, Very good, (1 review)
The price is CA $656
CA $787 total
includes taxes & fees
Aug 7 - Aug 8
7 Waves

16. 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 $350
CA $399 total
includes taxes & fees
Sep 1 - Sep 2
Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

17. Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Caravan - Sleeps 8 - Pets Ok - Parking - Patio
Camber Sands
The price is CA $240
CA $335 total
includes taxes & fees
Sep 2 - Sep 3
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

18. 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 $274
CA $403 total
includes taxes & fees
Aug 18 - Aug 19
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

19. Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (3 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
The price is CA $118
CA $142 total
includes taxes & fees
Aug 3 - Aug 4
Chestnut Meadow Camping

20. 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 $378
CA $427 total
includes taxes & fees
Aug 16 - Aug 17
Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!
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.

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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 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 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.