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Winchelsea Holiday Rentals

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Holiday Rentals in Winchelsea

Our top choices for Winchelsea holiday rentals

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

10.0 out of 10, Exceptional, (25)
"Greeted by three lovely sheep and the owners Karen and Peter, who were stellar from start to end.The place was very clean, comfortable and exactly as described. Would 100% book this place again. "
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, (86)
"Warm welcome, comfortable and very clean apartment. Well stocked kitchen for a longer self catering stay. Well situated for town, beach, restaurants etc. loved the fresh fruit in reception and the tea and coffee available. "
Osborne Apartments

Vive Hotel

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

Pinewood Camping Pods - At Port Lympne Reserve

2.0 star property
9.4 out of 10, Exceptional, (28)
"The staff are so friendly and helpfull and we all enjoyed out stay."
The price is AU$369
includes taxes & fees
9 Sept - 10 Sept
Pinewood Camping Pods - At Port Lympne Reserve

Grace Apartments - Living Rock

3.5 star property
4.8 out of 10, (5)
"I needed immediate help when the sat sav dumped me nearby & my host talked me all the way to the front door which was a huge relief. The accommodation is dated but I knew that from the photos it was very clean though & i was surprised to find all the essentials had ben left. I wasn’t expecting that so had brought it all with me. The bed was very comfortable, the shower was lovely & the washing machine was handy. The area was very noisy though as it is right in town above a bar & I was there at...
Grace Apartments - Living Rock

Extraordinary Huts

3.0 star property
9.6 out of 10, Exceptional, (38)
"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 AU$269
includes taxes & fees
15 Sept - 16 Sept
Extraordinary Huts

The Boathouse

3.0 star property
The price is AU$836
includes taxes & fees
13 Sept - 14 Sept
The Boathouse

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 AU$157
includes taxes & fees
6 Oct - 7 Oct
Bexlet

Entire Beach House, beautiful sea views & direct beach access on the Kent coast

10.0 out of 10, Exceptional, (57)
"nice property space for all the family ! weather beautiful ,so easy to walk along the beach."
Entire Beach House, beautiful sea views & direct beach access on the Kent coast

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

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 AU$674
includes taxes & fees
28 Sept - 29 Sept
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters

Tranquil Loft Apartment Overlooking Countryside

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

Big2vacation Exclusive Camber Sands Holiday Park

3.0 star property
The price is AU$435
includes taxes & fees
9 Sept - 10 Sept
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 AU$1,032
includes taxes & fees
9 Sept - 10 Sept
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .

Sandunes 1 (1 Bedroom) Sleeps 4

9.2 out of 10, Wonderful, (47)
"Fantastic stay, we loved this place. "
Sandunes 1 (1 Bedroom) Sleeps 4

Lilyrose Cottage

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"
The price is AU$869
includes taxes & fees
15 Sept - 16 Sept
Lilyrose Cottage

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!"
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.

Humphries Cross Apartments

3.0 star property
9.8 out of 10, Exceptional, (27)
"Lovely accommodation. Relaxing stay. "
Humphries Cross Apartments

2 Bedroom Boutique Apartment, close to Le Shuttle & the Port of Dover

The price is AU$267
includes taxes & fees
14 Sept - 15 Sept
2 Bedroom Boutique Apartment, close to Le Shuttle & the Port of Dover

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
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 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$157 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?

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.