A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winchelsea vacation rentals

Flat-screen TV

Grogu's Rest - 2 bedrooms with decking sleeps 6

Grogu's Rest - 2 bedrooms with decking sleeps 6
Winchelsea Beach
8.8 out of 10, Excellent, (8 reviews)
"great stay again"
United Kingdom
lindsay r.
$323 nightly
The price is $323
Jul 6 - Jul 7
Total with taxes and fees
Grogu's Rest - 2 bedrooms with decking sleeps 6
Exterior

White Haven - with 2 double rooms

White Haven - with 2 double rooms
Winchelsea Beach
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.
$308 nightly
The price is $308
Jul 2 - Jul 3
Total with taxes and fees
White Haven - with 2 double rooms
Cottage | Interior

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
$452 nightly
The price is $542
Jul 5 - Jul 6
Total with taxes and fees
Sparrows Den Lodge
Economy Cabin, Garden View

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (2 reviews)
"Really nice stay in lovely cabin."
United Kingdom
Mary
$83 nightly
The price is $99
Jul 2 - Jul 3
Total with taxes and fees
Chestnut Meadow Camping
1 bedroom, iron/ironing board, free WiFi, bed sheets

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
East Sussex
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
$142 nightly
The price is $142
Jul 7 - Jul 8
Total with taxes and fees
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
The Hide Out | Living room

Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (43 reviews)
"A stunningly beautiful setting. Clean, tidy and, elegantly decorated and set out. Secure, peaceful and comfortable. We shall most definitely stay there again. Cannot recommend highly enough! ✨💫✨💫✨💫💚🌲💚💫✨💫✨"
United Kingdom
Diana
$184 nightly
The price is $184
Jul 7 - Jul 8
Total with taxes and fees
Extraordinary Huts
Miscellaneous

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (54 reviews)
"Excellent little studio , has everything you need. Great location."
United Kingdom
Tim
$98 nightly
The price is $118
Jul 6 - Jul 7
Total with taxes and fees
Bexlet
Exterior

The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
$201 nightly
The price is $201
Jul 5 - Jul 6
Total with taxes and fees
The Field View 2 by Tiny Away
Exterior

Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite

Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
Flimwell, Wadhurst
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.
$146 nightly
The price is $146
Jul 5 - Jul 6
Total with taxes and fees
Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
Cottage | Exterior

Salthaven Shepherds Hut

Salthaven Shepherds Hut
2.0 star property
Pevensey
10.0 out of 10, Exceptional, (1 review)
"Beautiful and homely hut! Has everything you need for a relaxing get away. The garden is much larger than I thought as well as being enclosed for dogs! The hosts were really lovely, great communication and welcoming."
United Kingdom
Nicola
$334 nightly
The price is $400
Jul 10 - Jul 11
Total with taxes and fees
Salthaven Shepherds Hut
Cabin | 1 bedroom, iron/ironing board, free WiFi, bed sheets

Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
3.0 star property
Hythe
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
$82 nightly
The price is $98
Jul 21 - Jul 22
Total with taxes and fees
Pet Friendly Private Cabin Town Eurotunnel Beach
Exterior detail

Seashell Cove - 2 bedrooms sleeps 6

Seashell Cove - 2 bedrooms sleeps 6
Dymchurch
$308 nightly
The price is $308
Jul 2 - Jul 3
Total with taxes and fees
Seashell Cove - 2 bedrooms sleeps 6
Exterior detail

Ashland - 2 bedrooms with decking sleeps 4

Ashland - 2 bedrooms with decking sleeps 4
Hastings
$339 nightly
The price is $339
Jul 2 - Jul 3
Total with taxes and fees
Ashland - 2 bedrooms with decking sleeps 4
Property grounds

Birch - Flimwell Park Lodges

Birch - Flimwell Park Lodges
Ticehurst
10.0 out of 10, Exceptional, (1 review)
"very good clean room with excellent bathroom"
United States
james t.
$119 nightly
The price is $119
Jul 2 - Jul 3
Total with taxes and fees
Birch - Flimwell Park Lodges
Outdoor dining

Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom

Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.4 out of 10, Exceptional, (14 reviews)
"What a beautiful stay , peaceful , everything you could need for a well needed escape . Staff excellent , surroundings wonderful , bar / restaurant fantastic . Can’t wait to go back ."
United States
Anonymous traveler
$279 nightly
The price is $279
Jul 5 - Jul 6
Total with taxes and fees
Challenger - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Dining

Ocean Sea View Suite

Ocean Sea View Suite
Dymchurch
9.8 out of 10, Exceptional, (6 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.
$294 nightly
The price is $294
Jul 12 - Jul 13
Total with taxes and fees
Ocean Sea View Suite
1 bedroom, WiFi

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (6 reviews)
"We had a delightful stay in the Garden Room. So peaceful and spacious. The bi-folding doors to the garden were a perfect touch - along with the comfortable bed and great coffee machine. Highly recommend!"
United States
Anonymous traveler
$293 nightly
The price is $293
Jul 5 - Jul 6
Total with taxes and fees
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
1 bedroom, free WiFi, bed sheets

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.

Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Bexhill
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic location, perfect flat!"
United Kingdom
Mark S.
$167 nightly
The price is $167
Jul 2 - Jul 3
Total with taxes and fees
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Property grounds

The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom

The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom
Ashford
9.8 out of 10, Exceptional, (30 reviews)
"Thank you - we had a fantastic time and will definitely return! Host was responsive and very helpful, the local recommendations were perfect and we had the relaxing time we were after."
United States
Anonymous traveler
$269 nightly
The price is $269
Jul 3 - Jul 4
Total with taxes and fees
The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom
Cottage | Outdoor dining

Songbirds

Songbirds
3.0 star property
Tenterden
$312 nightly
The price is $375
Jul 12 - Jul 13
Total with taxes and fees
Songbirds
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

Holiday Inn Ashford North A20 by IHG

Holiday Inn Ashford North A20 by IHG

10/10 Excellent
"The staff were brilliant, the room was huge"
Andrew 1-night trip
Posted 3 hours ago
Holiday Inn Ashford North A20 by IHG

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 $85 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?

Six bedroom house with hot tub and sauna: This vacation home rental near Winchelsea offers a patio, a garden, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Winchelsea?

With 13 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 High Weald are a couple of lovely local spots to get outside and enjoy nature. Pett Level Beach 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.