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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, (28)
"Loved this place, fantastic value for money, beautiful walks, lovely people, great facilities quiet and relaxing."
United Kingdom
Katy T.
A luxurious self-catering retreat for two, complete with indoor pool & hot tub.
Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (87)
"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."
United Kingdom
Lucy
Osborne Apartments
Vive Hotel
4.0 star property
7.0 out of 10, Good, (84)
"The staff were amazing. "
United Kingdom
Paul
Vive Hotel
Extraordinary Huts
3.0 star property
9.6 out of 10, Exceptional, (39)
"We wanted quiet, peaceful, beautiful, unique and considerate and that’s what we got. To be woken up by pheasants and lambs, dinner at The Plough, logs being burnt inside and out and amazing views and walks… it was all there."
United Kingdom
Casey
The price is AU$274
includes taxes & fees
11 Nov - 12 Nov
Extraordinary Huts
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."
United Kingdom
georgina
The price is AU$295
includes taxes & fees
9 Nov - 10 Nov
Pinewood Camping Pods - At Port Lympne Reserve
16th Century Cottage Situated Opposite The Medieval Landgate Arch
9.4 out of 10, Exceptional, (186)
"Cosy homely cottage had a wonderful stay, short walk to everything."
United Kingdom
Beth
16th Century Cottage Situated Opposite The Medieval Landgate Arch
The Stables at Boreham House
5.0 star property
10.0 out of 10, Exceptional, (2)
"The property is lovely and separate from the mail house which is nice. The hosts are great and helped us out when we had to stay longer. As described and a great and relaxing boot hole. Particularly nice was milk in the fridge when we arrived for the available tea and coffee. A really nice touch!"
United Kingdom
Kate
The Stables at Boreham House
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"
United Kingdom
Brenda
Charming 1-bedroom Apartment Near South Downs
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.
10.0 out of 10, Exceptional, (16)
"Always a great stay at Heron Cottage, this was our 5th stay so this must prove we love it!"
United Kingdom
mark b.
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.
Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.
10.0 out of 10, Exceptional, (8)
"Extremely pleased with our stay. I would highly recommend it. "
United States
Jeffery Paul
Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.
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"
United Kingdom
Ann
The price is AU$156
includes taxes & fees
28 Oct - 29 Oct
Bexlet
Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12
9.6 out of 10, Exceptional, (47)
"Ideally situated for the beach, parking for 3 vehicles, spacious downstairs. "
United Kingdom
Martin H.
Stunning Spacious Seaside cottage, 1 minute from the beach sleeps 12
Outstanding luxury beachfront holiday experience with hot tub
10.0 out of 10, Exceptional, (110)
"Excellent house and a great location "
United Kingdom
David M.
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
East Sussex Manor | Sleeps 12 | Hot Tub & Parking
The price is AU$708
includes taxes & fees
29 Oct - 30 Oct
East Sussex Manor | Sleeps 12 | Hot Tub & Parking
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 "
United Kingdom
Laura J.
The price is AU$478
includes taxes & fees
25 Oct - 26 Oct
Beach Lodge - 5 minute walk to the sandy beach
Extra-large luxury Shepherd's Hut, private hot tub, Smart TV, wifi, fab views.
10.0 out of 10, Exceptional, (14)
"We had a really lovely weekend away, was very peaceful and quiet. Sam was a great host, good communication before we arrived and helped show us around☺️ would definitely stay again. "
United Kingdom
Keira
Extra-large luxury Shepherd's Hut, private hot tub, Smart TV, wifi, fab views.
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."
United Kingdom
Sima
Oastbrook Glamping
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...
United Kingdom
Tabassum A.
The price is AU$636
includes taxes & fees
2 Nov - 3 Nov
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
Big2vacation Exclusive Camber Sands Holiday Park
3.0 star property
The price is AU$434
includes taxes & fees
19 Nov - 20 Nov
Big2vacation Exclusive Camber Sands Holiday Park
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$156 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?

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

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.