A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

Winchelsea Holiday Rentals

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Our top choices for Winchelsea holiday rentals

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 AU$466
includes taxes & fees
27 July - 28 July
Grogu's Rest - 2 bedrooms with decking sleeps 6

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 AU$443
includes taxes & fees
29 July - 30 July
White Haven - with 2 double rooms

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
The price is AU$781
includes taxes & fees
2 Aug - 3 Aug
Sparrows Den Lodge

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 AU$279
includes taxes & fees
5 Aug - 6 Aug
Extraordinary Huts

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 AU$228
includes taxes & fees
28 July - 29 July
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

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 AU$143
includes taxes & fees
26 July - 27 July
Chestnut Meadow Camping

1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is AU$958
includes taxes & fees
2 Aug - 3 Aug
1A Coastguard Cottages

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 AU$410
includes taxes & fees
24 Aug - 25 Aug
Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

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 AU$383
includes taxes & fees
20 Aug - 21 Aug
Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Bluebell corner - with small enclosed decking

Bluebell corner - with small enclosed decking
Hastings
The price is AU$443
includes taxes & fees
2 Aug - 3 Aug
Bluebell corner - with small enclosed decking

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 AU$160
includes taxes & fees
10 Aug - 11 Aug
Bexlet

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 AU$466
includes taxes & fees
9 Aug - 10 Aug
Rhodown - sun on the terrace all round

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, (7 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 AU$388
includes taxes & fees
26 July - 27 July
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

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 AU$619
includes taxes & fees
29 July - 30 July
Charming 3-bedroom house in soothing Playden Rye neighborhood

Fir Tree - 2 bedrooms sleeps 5

Fir Tree - 2 bedrooms sleeps 5
Hastings
The price is AU$489
includes taxes & fees
6 Aug - 7 Aug
Fir Tree - 2 bedrooms sleeps 5

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 AU$758
includes taxes & fees
23 Aug - 24 Aug
2 bedroom accommodation in Rye

Lantern Cottage

Lantern Cottage
3.5 star property
Rye
The price is AU$872
includes taxes & fees
5 Aug - 6 Aug
Lantern Cottage

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 AU$986
includes taxes & fees
21 Aug - 22 Aug
RYE HOUSE: Central Location & WiFi

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 AU$426
includes taxes & fees
16 Aug - 17 Aug
Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Bexhill
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic location, perfect flat!"
United Kingdom
Mark S.
The price is AU$244
includes taxes & fees
27 July - 28 July
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
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 Hotel Reviews

Find out more about Winchelsea

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

Winchelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchelsea. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchelsea 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 holiday rentals we have selected for you start as low as AU$143 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchelsea rentals

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

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Frequently asked questions

Can I find holiday rentals in Winchelsea?

Yes, there are holiday rentals close to the most popular sights in Winchelsea, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

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

Converted barn / Oast House with amazing views and EV chargers: This holiday home rental outside of Winchelsea 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?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Winchelsea stay.

What’s there to see and do in Winchelsea?

Winchelsea Beach and High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach and St. Thomas the Martyr are other places to visit while you're in town.

What’s a holiday rental in Winchelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchelsea. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.