Winchelsea Holiday Rentals

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Holiday Rentals in Winchelsea

Aparthotel in Eastbourne

2.5 star property
9.0 out of 10, Wonderful, (90)
"great staff and facilities"
United Kingdom
Martin
Osborne Apartments

Camping in Hythe

2.0 star property
9.4 out of 10, Exceptional, (30)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
The price is AU$305
includes taxes & fees
5 Jan - 6 Jan 2026
Pinewood Camping Pods - At Port Lympne Reserve

Cabin in Rye

3.0 star property
9.6 out of 10, Exceptional, (41)
"Escaping to the country has never been more fun and magical. The resident robin and all his many friends keep you in that chilled mindset. The town of Rye was 10 mins by car and full of historical charm. It was even being used for filming while we visited. We walked from Rye to Camber sands along the cycle path and there are frequent buses back. "
United Kingdom
Meryl
Extraordinary Huts

Apartment in Hythe

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$262
includes taxes & fees
10 Dec - 11 Dec
1-bedroom Apartment Sleeps 4, Parking

Cabin in Romney Marsh

3.0 star property
The price is AU$339
includes taxes & fees
7 Jan - 8 Jan 2026
Big2vacation2 Exclusive at new Beach Caravan Park

Apartment in Bexhill

10.0 out of 10, Exceptional, (6)
"Perfect location. Perfectly comfortable."
United Kingdom
alex
The price is AU$234
includes taxes & fees
9 Dec - 10 Dec
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Apartment in Bexhill-on-Sea

2.0 star property
8.6 out of 10, Excellent, (50)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
The price is AU$159
includes taxes & fees
15 Dec - 16 Dec
Bexlet

Chalet in Rye

3.0 star property
The price is AU$424
includes taxes & fees
12 Dec - 13 Dec
Big2vacation Exclusive Camber Sands Holiday Park

Cottage in Broad Oak

9.8 out of 10, Exceptional, (216)
"We had a wonderful stay in a nice place. Everything we needed was there. "
Netherlands
Petra v.
Character Beamed Country Retreat with self check in/out in historic 1066 country

Cottage in Heathfield

3.5 star property
10.0 out of 10, Exceptional, (2)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
United Kingdom
Thomas
The price is AU$1,445
includes taxes & fees
4 Jan - 5 Jan 2026
Gun Hill Cottage

Cottage in fairlight

9.8 out of 10, Exceptional, (80)
"It was lovely, such a nice place to stay and an awesome view. "
Netherlands
Mildred v.
Coastguard Cottage With Sea Views

Apartment in Ashford

2.0 star property
Grace Apartments - Living Stone 2

Apartment in Hailsham

3.0 star property
10.0 out of 10, Exceptional, (1)
Tranquil Loft Apartment Overlooking Countryside

Apartment in Saint Leonards

9.4 out of 10, Exceptional, (48)
"Great location, stunning views. Everything we needed for a short stay. Very comfy bed. Thank you, would book again"
United Kingdom
Sara B.
Seafront, direct ocean view, beautiful balcony, spacious flat

Cottage in Rye

10.0 out of 10, Exceptional, (9)
"We stayed here for a weekend, to attend a wedding nearby - two adults and two children (aged 5 & 9). The configuration of the apartment was perfect: there are two double beds on the top floor, all kind of in the same room but separated by a wall (it makes sense once you see it), which was perfect for us. Really, really cute place oozing with character, and a very friendly vibe (again, that makes sense once you see it). Well provisioned kitchen (our catering needs didn't extend beyond making...
United Kingdom
Nick J.
The price is AU$484
includes taxes & fees
6 Jan - 7 Jan 2026
An unusual two-storey apartment with beams and an open fire.

Holiday Home in Lydd

9.6 out of 10, Exceptional, (8)
"Although an old pub this is an excellent place for friends and family to stay for a celebration or to explore the surrounding area. Very clean and a great kitchen, Bedrooms vary but all comfortable. Overall very good."
United Kingdom
Leonard R.
A fabulous Grade II listed converted 14th Century pub. Child and pet friendly

Holiday Home in Hellingly /Hailsham

7.6 out of 10, Good, (9)
"The property was incredible and the host had incredible communication. Maria could not have been more accommodating and we cannot thank her enough, we had a fabulous stay and hope to be back soon."
United Kingdom
Matilda B.
The price is AU$1,091
includes taxes & fees
5 Jan - 6 Jan 2026
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Cabin in Rye

3.0 star property
4.0 out of 10, (2)
"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$346
includes taxes & fees
16 Dec - 17 Dec
Cozy Camber Caravan 3 Bedroom Retreat With Decking

Cottage in Pevensey

3.0 star property
10.0 out of 10, Exceptional, (1)
"All very good. However too many disabled parking spaces meaning too few for others"
United Kingdom
Graeme
The price is AU$847
includes taxes & fees
12 Dec - 13 Dec
Lilyrose Cottage

Holiday Home in Hythe

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a lovely experience from start to finish, our 10yr wedding anniversary and it was perfect, Lovely location, property was good size, owner has thought of every little detail, the hot tub, sauna and cinema room was lush!! Didn’t Really have to go anywhere, close to town with shops, and lovely country walks! Would definitely return soon and bring our children with us! "
United Kingdom
Marie
ELEVATED ESCAPE - 3 bedroom house with rooftop terrace,sauna,hot tub&cinema room
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$159 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. 

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?

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly: This holiday home rental outside of Winchelsea offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Winchelsea?

With 5 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.