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Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

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.
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."
Osborne Apartments
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."
The price is ￥29,823
￥35,788 total
includes taxes & fees
Oct 1 - Oct 2
Pinewood Camping Pods - At Port Lympne Reserve
Vive Hotel
Exterior

Vive Hotel

4.0 star property
7.0 out of 10, Good, (84)
"The staff were amazing. "
Vive Hotel
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."
The price is ￥28,325
￥28,325 total
includes taxes & fees
Sep 29 - Sep 30
Extraordinary Huts
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
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
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, (6)
"Extremely pleased with our stay. I would highly recommend it. "
Waterloo Terrace -Historical luxury apartment in heart of Old Town with balcony.
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"
The price is ￥12,655
￥15,187 total
includes taxes & fees
Oct 6 - Oct 7
Bexlet
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
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
2 bedroomed cottage in Hythe, Kent, close to amenities and beach. Dogs welcome.
Exterior

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
Beach

Humphries Cross Apartments

3.0 star property
9.8 out of 10, Exceptional, (27)
"Lovely accommodation. Relaxing stay. "
Humphries Cross Apartments
Stunning Sea Front Apartment
Smart TV, books, stereo

Stunning Sea Front Apartment

9.6 out of 10, Exceptional, (32)
"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
The price is ￥29,866
￥35,839 total
includes taxes & fees
Sep 29 - Sep 30
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."
The price is ￥53,054
￥96,816 total
includes taxes & fees
Sep 29 - Sep 30
Hidden gem with hot tub and tennis court in idyllic East Sussex countryside .
Big2vacation2 Exclusive at new Beach Caravan Park
Property grounds

Big2vacation2 Exclusive at new Beach Caravan Park

3.0 star property
The price is ￥35,136
￥42,163 total
includes taxes & fees
Sep 29 - Sep 30
Big2vacation2 Exclusive at new Beach Caravan Park
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...
The price is ￥5,803
￥55,560 total
includes taxes & fees
Sep 29 - Sep 30
Huge 6 bedroom house, near beach, cliffs & Old Town, 180 square meters
Lovely 1 Bedroom Ground Floor Apartment max 4 per
Apartment | Living area | TV

Lovely 1 Bedroom Ground Floor Apartment max 4 per

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is ￥20,863
￥25,035 total
includes taxes & fees
Oct 6 - Oct 7
Lovely 1 Bedroom Ground Floor Apartment max 4 per
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 Relais Cooden Beach

The Relais Cooden Beach

10/10 Excellent
"First time here since updating and very impressed. Room was comfortable and spacious.Only sorry that the weather prevented us from making use of the private terrace. Helpful and frienly staff. Super restaurant. Will be back"
John 1-night trip
Posted 2 days ago
The Relais Cooden Beach

Find out more about Winchelsea

Find out more about Winchelsea

Search for holiday rentals in Winchelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchelsea using one of the methods below:

  • View our selection of featured holiday rentals in Winchelsea
  • Use the map to find apartments and other holiday homes in the Winchelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchelsea while they last

Look no further and take a look at our great range of rental properties in Winchelsea!

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.