Winchelsea Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

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.
$312 nightly
The price is $312
May 28 - May 29
Total with taxes and fees
Grogu's Rest - 2 bedrooms with decking sleeps 6
Cottage | Interior

Sparrows Den Lodge

Sparrows Den Lodge
3.5 star property
Winchelsea
$458 nightly
The price is $549
May 28 - May 29
Total with taxes and fees
Sparrows Den Lodge
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.
$296 nightly
The price is $296
Jun 1 - Jun 2
Total with taxes and fees
White Haven - with 2 double rooms
Economy Cabin, Garden View

Chestnut Meadow Camping

Chestnut Meadow Camping
1.0 star property
Bexhill-on-Sea
10.0 out of 10, Exceptional, (1 review)
"Really nice stay in lovely cabin."
United Kingdom
Mary
$91 nightly
The price is $110
May 30 - May 31
Total with taxes and fees
Chestnut Meadow Camping
Exterior

Oastbrook Glamping

Oastbrook Glamping
2.0 star property
Robertsbridge
10.0 out of 10, Exceptional, (1 review)
"Nick and America are wonderful hosts. The bed and pillows were so comfortable. We loved our stay there and cannot wait to go back."
United Kingdom
Sima
$188 nightly
The price is $225
May 31 - Jun 1
Total with taxes and fees
Oastbrook Glamping
Exterior detail

Ashland - 2 bedrooms with decking sleeps 4

Ashland - 2 bedrooms with decking sleeps 4
Hastings
$328 nightly
The price is $328
May 27 - May 28
Total with taxes and fees
Ashland - 2 bedrooms with decking sleeps 4
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
$144 nightly
The price is $144
May 25 - May 26
Total with taxes and fees
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
Exterior

The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
$203 nightly
The price is $203
May 26 - May 27
Total with taxes and fees
The Field View 2 by Tiny Away
The Hide Out | Living room

Extraordinary Huts

Extraordinary Huts
3.0 star property
Rye
9.6 out of 10, Exceptional, (42 reviews)
"Lovely stay at The Hut."
United Kingdom
Nicholas
$196 nightly
The price is $196
Jun 24 - Jun 25
Total with taxes and fees
Extraordinary Huts
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
$83 nightly
The price is $99
Jun 19 - Jun 20
Total with taxes and fees
Pet Friendly Private Cabin Town Eurotunnel Beach
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.
$148 nightly
The price is $148
Jun 3 - Jun 4
Total with taxes and fees
Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
Cottage | Outdoor dining

Songbirds

Songbirds
2.0 star property
Tenterden
$316 nightly
The price is $380
Jun 1 - Jun 2
Total with taxes and fees
Songbirds
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.
$169 nightly
The price is $169
May 25 - May 26
Total with taxes and fees
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
Exterior

Rumwold by Bloom Stays - a rural shepherds hut sleeping 2 with amazing views!

Rumwold by Bloom Stays - a rural shepherds hut sleeping 2 with amazing views!
Ashford
9.8 out of 10, Exceptional, (44 reviews)
"We absolutely adored our stay with you! Everything was immaculate and everything was thought of. Thank you and we can't wait to return again!"
United States
Anonymous traveler
$273 nightly
The price is $273
May 27 - May 28
Total with taxes and fees
Rumwold by Bloom Stays - a rural shepherds hut sleeping 2 with amazing views!
Miscellaneous

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.6 out of 10, Excellent, (52 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
$88 nightly
The price is $106
Jun 8 - Jun 9
Total with taxes and fees
Bexlet
Exterior detail

Seashell Cove - 2 bedrooms sleeps 6

Seashell Cove - 2 bedrooms sleeps 6
Dymchurch
$296 nightly
The price is $296
May 27 - May 28
Total with taxes and fees
Seashell Cove - 2 bedrooms sleeps 6
Interior

Weeping Willow - 3 bedrooms with decking sleeps 8

Weeping Willow - 3 bedrooms with decking sleeps 8
Camber
$296 nightly
The price is $296
Jun 1 - Jun 2
Total with taxes and fees
Weeping Willow - 3 bedrooms with decking sleeps 8
Luxury Cabin | Living area | TV

Pinewood Camping Pods - At Port Lympne Reserve

Pinewood Camping Pods - At Port Lympne Reserve
2.0 star property
Hythe
9.6 out of 10, Exceptional, (34 reviews)
"The room was so cosy, clean and designed well. "
United Kingdom
Bindu
$216 nightly
The price is $259
Jun 24 - Jun 25
Total with taxes and fees
Pinewood Camping Pods - At Port Lympne Reserve
Interior

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

Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Tenterden
9.6 out of 10, Exceptional, (14 reviews)
"We had a great stay at Goldings. The accommodation was lovely and the hot tub was great. The staff were all really friendly and helpful. The food and drink on site was great too."
United States
Anonymous traveler
$273 nightly
The price is $273
May 25 - May 26
Total with taxes and fees
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

2 Bedroom Boutique Apartment, close to Le Shuttle & the Port of Dover
Mersham
$215 nightly
The price is $215
May 26 - May 27
Total with taxes and fees
2 Bedroom Boutique Apartment, close to Le Shuttle & the Port of Dover
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 Chatsworth Hotel

The Chatsworth Hotel

10/10 Excellent
"A beautiful hotel right on the seafront. The staff are excellent and all of the amenities are fantastic. From the coffee in the lounge, cocktails in the bar and breakfast in the restaurant, it was all lovely. The room was huge as was the bathroom, with a gorgeous sea view. Dinner in the restaurant was complimented by a free drink on our first night. The food was lovely and the live pianist added wonderful ambience. The only niggles are that the dinner menu is a little restrictive for vegetarian/vegan diets and that room service for the breakfast took a while as they were busy but these are first world problems!"
Emma 2-night trip
Posted 2 hours ago
The Chatsworth Hotel

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 $106 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?

Burlington Palace, Huge Sea front Villa, Super King suites, velvet dining room: This vacation home rental near Winchelsea offers a patio, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winchelsea?

With 7 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.