Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Winchelsea vacation rentals

Terrace/patio

Cottage in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (11 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
$379 nightly
The price is $379
Feb 5 - Feb 6
Total with taxes and fees
1 bedroom accommodation in Winchelsea Beach, near Rye
Cottage | Interior

Vacation Home in Winchelsea

Sparrows Den Lodge
3.5 star property
$432 nightly
The price is $518
Jan 31 - Feb 1
Total with taxes and fees
Sparrows Den Lodge
Exterior

Apartment in Winchelsea Beach

White Haven - with 2 double rooms
2.0 out of 10, (1 review)
"Check in was easy and location was good, thise are the only positives. The property is extremely dated and dirty. The furnishings in communal areas were torn, threadbare, stained, dirty and smelly. The carpets were dirty, covered in dog and human hair. There was mould above the shower and dirt and mould under the sink. The areas around the toilets were soiled with rusted old urine splashes. There was mould on one of the bedroom walls.The kitchen cupboard fascias were peeling and the handles all...
United Kingdom
Emma V.
$337 nightly
The price is $337
Jan 25 - Jan 26
Total with taxes and fees
White Haven - with 2 double rooms
Exterior

Camping in Bexhill-on-Sea

Chestnut Meadow Camping
1.0 star property
$93 nightly
The price is $112
Jan 22 - Jan 23
Total with taxes and fees
Chestnut Meadow Camping
Luxury Cabin | Living area | TV

Camping in Hythe

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
9.6 out of 10, Exceptional, (31 reviews)
"The staff are so friendly and helpfull and we all enjoyed out stay."
United Kingdom
georgina
$169 nightly
The price is $203
Jan 22 - Jan 23
Total with taxes and fees
Pinewood Camping Pods - At Port Lympne Reserve
TV

Mobile Home in Hastings

Victory - idyllic holiday home in Hastings
10.0 out of 10, Exceptional, (1 review)
"Nice and Memorable stay "
United Kingdom
Kishore S.
$337 nightly
The price is $337
Jan 24 - Jan 25
Total with taxes and fees
Victory - idyllic holiday home in Hastings
House, 1 Bedroom, Garden View | Garden

Apartment in Ashford

Calm Private Annex Ideal to Work, Rest & Explore
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"One night stay to visit local family. Very welcoming, met on arrival. Coldest night of the year so far and it was warm, cosy & comfortable. Owners live next door, attached house, easy parking, easy to find. Will possibly be return during 2026, central location for all our needs."
United Kingdom
Steve
$94 nightly
The price is $113
Feb 10 - Feb 11
Total with taxes and fees
Calm Private Annex Ideal to Work, Rest & Explore
Miscellaneous

Apartment in Bexhill-on-Sea

Bexlet
2.0 star property
8.6 out of 10, Excellent, (50 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
$88 nightly
The price is $106
Jan 25 - Jan 26
Total with taxes and fees
Bexlet
Deluxe Apartment | Free WiFi

Aparthotel in Eastbourne

Osborne Apartments
2.5 star property
9.0 out of 10, Wonderful, (96 reviews)
"Great stay"
United Kingdom
George
Osborne Apartments
Property grounds

Cabin in East Sussex

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
10.0 out of 10, Exceptional, (11 reviews)
"Fabulous host. Private cabin, lovely log burner, absolutely magnificent bed ! Shower was great, everything you could need, like milk in the fridge, great coffee etc. lovely view in the morning of the horses, donkey and pony in the fields. Look forward to staying there again !"
United Kingdom
Mark
$156 nightly
The price is $156
Jan 25 - Jan 26
Total with taxes and fees
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
TV

Mobile Home in Camber

Beach Lodge - 5 minute walk to the sandy beach
8.8 out of 10, Excellent, (10 reviews)
"Fantastic lodge near the beach on a great location in the park. Highly recommend "
United Kingdom
Laura J.
$353 nightly
The price is $353
Jan 26 - Jan 27
Total with taxes and fees
Beach Lodge - 5 minute walk to the sandy beach
TV

Vacation Home in Sussex

Camber Sands Holiday Park
2.0 star property
$173 nightly
The price is $173
Feb 13 - Feb 14
Total with taxes and fees
Camber Sands Holiday Park
Cabin | 1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in Hythe

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
8.0 out of 10, Very Good, (3 reviews)
"The closeness to the High St. meant it was easy to walk to find something to eat/drink. The host was very helpful."
United Kingdom
David
$83 nightly
The price is $99
Feb 5 - Feb 6
Total with taxes and fees
Pet Friendly Private Cabin Town Eurotunnel Beach
TV

Mobile Home in Hastings

Rhodown - sun on the terrace all round
9.2 out of 10, Wonderful, (5 reviews)
"Lovely peaceful setting and the caravan had everything you would need and bonus being so close to Hastings"
United Kingdom
William E.
$354 nightly
The price is $354
Jan 24 - Jan 25
Total with taxes and fees
Rhodown - sun on the terrace all round
Dining

Apartment in Dymchurch

Ocean Sea View Suite
10.0 out of 10, Exceptional, (4 reviews)
"Our stay at the Ocean Sea View Suite was lovely. We had a great experience from the booking to the checkout. The property is well kept and clean. Amazing location with shops, food and entertainment options just on the door step. The cherry on the cake was the beautiful sandy beach. "
United Kingdom
Djanicie M.
$210 nightly
The price is $252
Jan 25 - Jan 26
Total with taxes and fees
Ocean Sea View Suite
Exterior

Cabin in Flimwell, Wadhurst

Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
9.4 out of 10, Exceptional, (3 reviews)
"Our trip to the Shepherds Hut was nothing short of idyllic! Our host Jay was so helpful and kind, even going so far as to give us a lift to Tunbridge Wells when our pre-booked taxi didn't show up. The outdoor kitchen was so easy to use, and made an al fresco breakfast very lovely. We took full advantage of the firepit - logs and kindling provided for us - as well as the lovely walks nearby. I would recommend to anyone looking to get away for a bit of peace and beauty!"
United Kingdom
Josi K.
$123 nightly
The price is $123
Jan 26 - Jan 27
Total with taxes and fees
Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
Exterior

Vacation Home in Hastings

Family Caravan Rental 2 bed Caravan
2.0 star property
$139 nightly
The price is $155
Feb 5 - Feb 6
Total with taxes and fees
Family Caravan Rental 2 bed Caravan
Cottage | Living area

Cottage in Heathfield

Gun Hill Cottage
3.5 star property
10.0 out of 10, Exceptional, (2 reviews)
"Gun Hill Cottage is a truly charming little place, really clean, nicely decorated, with everything you need. Chris was an amazing host, let us know all the details in advance, then checked in by email that everything was good. we really enjoyed our stay. Thanks! Tom"
United Kingdom
Thomas
$822 nightly
The price is $987
Jan 25 - Jan 26
Total with taxes and fees
Gun Hill Cottage
2 bedrooms, iron/ironing board, travel crib, WiFi

Cottage in Mersham

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
10.0 out of 10, Exceptional, (3 reviews)
"WE had an excellent stay with our two young grandchildren. It was perfectly located as we had visited Chatham historic dockyard and spending the next day at Tenterden heritage railway. So much so the youngest wanted to stay an extra night! The description is spot on, Our host extremely helpful with local knowledge. Highly recommend "
United Kingdom
Malcolm T.
$204 nightly
The price is $204
Feb 2 - Feb 3
Total with taxes and fees
2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
Living area

Cottage in Cowbeech, near Hailsham

1 bedroom accommodation in Cowbeech, near Hailsham
10.0 out of 10, Exceptional, (2 reviews)
"Cedar Lodge was exactly what we were looking for and we felt at home as soon as we arrived. The accommodation was clean, cosy and very well equipped and the hosts Caroline and Neil were very welcoming. The comments in the visitors book showed that many people have visited here several times and feel it’s the best holiday home they have stayed in. The location is very quiet and the view from the deck is beautiful. I wouldn’t hesitate to stay here again if we are visiting the area."
United States
Carolyn Armstrong
$207 nightly
The price is $207
Jan 22 - Jan 23
Total with taxes and fees
1 bedroom accommodation in Cowbeech, near Hailsham
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

Hampton by Hilton Ashford International

Hampton by Hilton Ashford International

10/10 Excellent
"Consistent with the Hampton’s experience in Canterbury minus the historic setting. Comfortable room with a 55” Samsung TV, 70-90Mbs broadband as standard, large shower and rich breakfast buffet."
Karl 1-night trip
Posted 2 days ago
Hampton by Hilton Ashford International

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 $176 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

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?

A fabulous Grade II listed converted 14th Century pub. Child and pet friendly: This vacation home near Winchelsea offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Winchelsea?

With 6 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.