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Winchelsea Beach Holiday Rentals

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Our top choices for Winchelsea Beach holiday 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 NZ$560
includes taxes & fees
22 Aug - 23 Aug
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 NZ$505
includes taxes & fees
17 Sept - 18 Sept
White Haven - with 2 double rooms

3. Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is NZ$939
includes taxes & fees
31 Aug - 1 Sept
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 NZ$346
includes taxes & fees
1 Sept - 2 Sept
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 NZ$324
includes taxes & fees
20 Aug - 21 Aug
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 NZ$172
includes taxes & fees
23 Aug - 24 Aug
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 NZ$399
includes taxes & fees
1 Sept - 2 Sept
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

8. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is NZ$1,152
includes taxes & fees
3 Sept - 4 Sept
1A Coastguard Cottages

9. Hillside retreat - 2 bedrooms sleeps 5

Hillside retreat - 2 bedrooms sleeps 5
Hastings
The price is NZ$505
includes taxes & fees
6 Sept - 7 Sept
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.
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 NZ$438
includes taxes & fees
17 Sept - 18 Sept
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 NZ$441
includes taxes & fees
13 Sept - 14 Sept
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 NZ$592
includes taxes & fees
27 Aug - 28 Aug
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 NZ$204
includes taxes & fees
13 Sept - 14 Sept
Bexlet

15. Bluebell corner - with small enclosed decking

Bluebell corner - with small enclosed decking
Hastings
The price is NZ$505
includes taxes & fees
1 Sept - 2 Sept
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 traveller
The price is NZ$468
includes taxes & fees
20 Aug - 21 Aug
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 NZ$587
includes taxes & fees
20 Aug - 21 Aug
Fir Tree - 2 bedrooms sleeps 5

18. South Beach Landings 0028

South Beach Landings 0028
2.0 star property
Rye
The price is NZ$1,091
includes taxes & fees
1 Sept - 2 Sept
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 NZ$532
includes taxes & fees
1 Sept - 2 Sept
Rhodown - sun on the terrace all round

20. Monument - 2 bedrooms sleeps 4

Monument - 2 bedrooms sleeps 4
Hastings
The price is NZ$532
includes taxes & fees
9 Sept - 10 Sept
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

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, 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 NZ$172 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?

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

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.