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Winchelsea Vacation Rentals

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Winchelsea

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

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
Garden

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."
$160 nightly
The price is $192
Nov 3 - Nov 4
Total with taxes and fees
Pinewood Camping Pods - At Port Lympne Reserve
Osborne Apartments
Deluxe Apartment | 1 bedroom, free WiFi

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."
$111 nightly
The price is $133
Oct 5 - Oct 6
Total with taxes and fees
Osborne Apartments
Vive Hotel
Exterior

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
Outdoor dining

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
The Hide Out | Living room

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."
$187 nightly
The price is $187
Oct 8 - Oct 9
Total with taxes and fees
Extraordinary Huts
Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.
Fridge, microwave, oven, stovetop

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
Dining

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
Fridge, microwave, oven, stovetop

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
Apartment | Balcony

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
Property grounds

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
Apartment | 1 bedroom, free WiFi, bed sheets

Tranquil Loft Apartment Overlooking Countryside

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

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"
$85 nightly
The price is $102
Oct 14 - Oct 15
Total with taxes and fees
Bexlet
Oastbrook Glamping
Exterior

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
Fridge, microwave, oven, stovetop

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 "
$218 nightly
The price is $312
Oct 4 - Oct 5
Total with taxes and fees
Beach Lodge - 5 minute walk to the sandy beach
* Stylish * Central * Sea View * Modern
Fridge, microwave, oven, stovetop

* 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
Smart TV, books, stereo

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
Cabin | Children's area

Big2vacation Exclusive Camber Sands Holiday Park

3.0 star property
$236 nightly
The price is $284
Nov 2 - Nov 3
Total with taxes and fees
Big2vacation Exclusive Camber Sands Holiday Park
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
Smart TV, DVD player, books

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."
$810 nightly
The price is $810
Oct 6 - Oct 7
Total with taxes and fees
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
Interior

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...
$372 nightly
The price is $372
Oct 6 - Oct 7
Total with taxes and fees
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

The View Hotel

The View Hotel

10/10 Excellent
"Have stayed here many times before and always feel happy to return. Good value for money especially refurbished rooms on the sixth floor with bathroom with walk in shower. "
mark 1-night trip
Posted 3 days ago
The View Hotel

Find out more about Winchelsea

Find out more about Winchelsea

Everything you need to know about Winchelsea vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchelsea vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchelsea in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchelsea rentals

At Expedia, we put the best Winchelsea vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winchelsea?

Yes, we have vacation rentals near well known local attractions in Winchelsea, or you can select a more secluded option if you're looking for relaxation. Our travelers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What's the top vacation rental that Winchelsea has to offer?

Converted barn / Oast House with amazing views and EV chargers: This vacation home rental near Winchelsea is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in Winchelsea?

With 4 Expedia vacation rentals, you're sure 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 vacation rental in Winchelsea like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchelsea. Vacation rentals feature extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.