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Winchelsea Holiday Rentals

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Holiday Rentals in Winchelsea

A luxurious self-catering retreat for two, complete with indoor pool & hot tub.

10.0 out of 10, Exceptional, (26)
"Loved this place, fantastic value for money, beautiful walks, lovely people, great facilities quiet and relaxing."
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.

Pinewood Camping Pods - At Port Lympne Reserve

2.0 star property
9.4 out of 10, Exceptional, (29)
"The staff are so friendly and helpfull and we all enjoyed out stay."
The price is NZ$415
includes taxes & fees
5 Oct - 6 Oct
Pinewood Camping Pods - At Port Lympne Reserve

Osborne Apartments

2.5 star property
9.0 out of 10, Wonderful, (86)
"JUST FANTASTIC check in - Shree was SO helpful and showed us our room and how to check out. It was incredible service. Loved the room, the kitchen and it was just wonderful. Will be staying again soon."
Osborne Apartments

Vive Hotel

4.0 star property
7.0 out of 10, Good, (84)
"The staff were amazing. "
Vive Hotel

16th Century Cottage Situated Opposite The Medieval Landgate Arch

9.6 out of 10, Exceptional, (184)
"Cosy homely cottage had a wonderful stay, short walk to everything."
16th Century Cottage Situated Opposite The Medieval Landgate Arch

Extraordinary Huts

3.0 star property
9.6 out of 10, Exceptional, (39)
"Beautiful views and great communication from the owner on how to find it and access your hut. We stayed in The Hive for one night and it was a little dusty, everything needed a deep clean. It didn’t ruin our trip, and would visit again in the hope this was a one off error."
The price is NZ$315
includes taxes & fees
16 Oct - 17 Oct
Extraordinary Huts

Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.

10.0 out of 10, Exceptional, (7)
"Extremely pleased with our stay. I would highly recommend it. "
Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.

Converted barn / Oast House with amazing views and EV chargers

10.0 out of 10, Exceptional, (69)
"Fantastic, idyllic, picturesque. A wonderful place to celebrate your 60th birthday with your family "
Converted barn / Oast House with amazing views and EV chargers

Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town

9.2 out of 10, Wonderful, (137)
"Very nice place to stay we really enjoyed :-)"
Modern 2 Bedroom Apartment In The Heart Of Historic Hastings Old Town

Charming 1-bedroom Apartment Near South Downs

3.0 star property
10.0 out of 10, Exceptional, (7)
"Everything we needed, just like home from home and in a lovely quiet location"
Charming 1-bedroom Apartment Near South Downs

Outstanding luxury beachfront holiday experience with hot tub

10.0 out of 10, Exceptional, (110)
"Excellent house and a great location "
Outstanding luxury beachfront holiday experience with hot tub

Tranquil Loft Apartment Overlooking Countryside

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

Bexlet

2.0 star property
8.6 out of 10, Excellent, (50)
"Easy to find on Sat Nav, parking nearby, very light, warm and comfortable, bed a little hard for us oldies. Overall great. Thank you"
The price is NZ$176
includes taxes & fees
13 Oct - 14 Oct
Bexlet

Oastbrook Glamping

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
Oastbrook Glamping

Beach Lodge - 5 minute walk to the sandy beach

8.8 out of 10, Excellent, (9)
"Fantastic lodge near the beach on a great location in the park. Highly recommend "
The price is NZ$537
includes taxes & fees
4 Oct - 5 Oct
Beach Lodge - 5 minute walk to the sandy beach

* Stylish * Central * Sea View * Modern

9.4 out of 10, Exceptional, (22)
"Excellent location and Communications. Enjoyed the walks along the beach"
* Stylish * Central * Sea View * Modern

Stunning Sea Front Apartment

9.6 out of 10, Exceptional, (34)
"The cutest coastal town "
Stunning Sea Front Apartment

Big2vacation Exclusive Camber Sands Holiday Park

3.0 star property
The price is NZ$489
includes taxes & fees
2 Nov - 3 Nov
Big2vacation Exclusive Camber Sands Holiday Park

Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

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."
The price is NZ$1,396
includes taxes & fees
6 Oct - 7 Oct
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters

"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...
The price is NZ$640
includes taxes & fees
6 Oct - 7 Oct
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
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

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 favorite 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 depends 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 NZ$176 per night. Entering your travel dates in the search wizard you might find 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?

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 4 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 Pett Level Beach are a couple of lovely local spots to get outside and enjoy nature. High Weald 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.