Winchelsea Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Winchelsea vacation rentals

Terrace/patio

1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
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
$427 nightly
The price is $427
May 13 - May 14
Total with taxes and fees
1 bedroom accommodation in Winchelsea Beach, near Rye
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.
$314 nightly
The price is $314
May 11 - May 12
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
$462 nightly
The price is $554
May 13 - May 14
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.
$298 nightly
The price is $298
May 17 - May 18
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
$93 nightly
The price is $111
May 14 - May 15
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
$191 nightly
The price is $229
May 14 - May 15
Total with taxes and fees
Oastbrook Glamping
TV

Bayview Retreat - 3 bedrooms with decking sleeps 6

Bayview Retreat - 3 bedrooms with decking sleeps 6
Pevensey Bay
8.0 out of 10, Very Good, (1 review)
"Despite the house being described as "very nice and clean," the presence of white dog hairs on the carpet and sofa was a major disappointment. This issue not only affected the appearance of the house, but also caused practical issues such as getting dog hair on our clothes. As someone with an allergy to dog hair, this made my stay uncomfortable and not as enjoyable as it could have been. As long as I am sure that the hair will be cleaned properly, I would go back with my family the next time."
United Kingdom
Blanka
$298 nightly
The price is $298
May 10 - May 11
Total with taxes and fees
Bayview Retreat - 3 bedrooms with decking sleeps 6
Exterior

The Field View 2 by Tiny Away

The Field View 2 by Tiny Away
Egerton
$205 nightly
The price is $205
May 11 - May 12
Total with taxes and fees
The Field View 2 by Tiny Away
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
$145 nightly
The price is $145
May 19 - May 20
Total with taxes and fees
Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest
2 bedrooms, iron/ironing board, travel crib, WiFi

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.

2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
Mersham
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.
$206 nightly
The price is $206
May 11 - May 12
Total with taxes and fees
2 bed Cosy cottage in the village of mersham Ashford nextdoor to pub and shop.
Cottage | Exterior

Combe Haven Holiday Park - Holiday Accommodation 12122

Combe Haven Holiday Park - Holiday Accommodation 12122
2.5 star property
St Leonards-On-Sea
$341 nightly
The price is $409
May 13 - May 14
Total with taxes and fees
Combe Haven Holiday Park - Holiday Accommodation 12122
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
$198 nightly
The price is $198
May 11 - May 12
Total with taxes and fees
Extraordinary Huts
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, (29 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
$349 nightly
The price is $349
May 10 - May 11
Total with taxes and fees
The Romney - a Shepherds Hut by Bloom Stays that sleeps 4 guests in 1 bedroom
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.
$150 nightly
The price is $150
May 11 - May 12
Total with taxes and fees
Luxury Shepherds Hut, W/large Garden, Firepit, & Wi-fi @ Cedar Gables Campsite
Fishing

1 bedroom accommodation in Pevensey Bay, near Eastbourne

1 bedroom accommodation in Pevensey Bay, near Eastbourne
Pevensey Bay, near Eastbourne
10.0 out of 10, Exceptional, (13 reviews)
"We. Had a lovely holiday right near the beach had some lovely walks. The accommodation was very nice and clean. The owner was excellent and very accommodating if we needed anything."
United States
Christine Sheen
$328 nightly
The price is $328
Jun 5 - Jun 6
Total with taxes and fees
1 bedroom accommodation in Pevensey Bay, near Eastbourne
Miscellaneous

Bexlet

Bexlet
2.0 star property
Bexhill-on-Sea
8.8 out of 10, Excellent, (51 reviews)
"A very peaceful place for a weekend getaway."
United Kingdom
Ian
$90 nightly
The price is $108
May 12 - May 13
Total with taxes and fees
Bexlet
1 bedroom, iron/ironing board, WiFi, bed sheets

Pet Friendly Private Cabin Town Eurotunnel Beach

Pet Friendly Private Cabin Town Eurotunnel Beach
Hythe
9.0 out of 10, Wonderful, (2 reviews)
"Property clean & adequate...owner very pleasant & helpful."
United Kingdom
Jayne
$100 nightly
The price is $100
May 13 - May 14
Total with taxes and fees
Pet Friendly Private Cabin Town Eurotunnel Beach
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
$275 nightly
The price is $275
May 11 - May 12
Total with taxes and fees
Goldings - a holiday let by Bloom Stays that sleeps 3 guests in 1 bedroom
Bar (on property)

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom

Pilgrim - a holiday let that sleeps 2 guests in 1 bedroom
Tenterden
10.0 out of 10, Exceptional, (1 review)
"Has everything you need. Very clean and comfortable. Only problem was the light coming in early in the morning, may want to take a sleep mask with you if you’re a light sleeper. Other thank that could not fault it."
United States
Rebecca J.
$320 nightly
The price is $320
May 11 - May 12
Total with taxes and fees
Pilgrim - 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, (6 reviews)
"Fantastic location, perfect flat!"
United Kingdom
Mark S.
$171 nightly
The price is $171
May 19 - May 20
Total with taxes and fees
Bexhill Town Centre Flat - Less than 5 mins to the iconic De La Warr Pavillion.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchelsea Hotel Reviews

The View Hotel

The View Hotel

8/10 Good
"Excellent location. We booked a sea view through a third party online agent and on arrival that room had been oversold so we were allocated a side view room. While not what we booked the view from that room was still lovely and the hotel is so well designed it was hardly a side view. The staff were lovely and the room had everything we needed. Breakfast was all self service but with a good selection and decent quality. For reasons we didn’t understand, the bar which was crowded at peak times and difficult to find a seat, was air conditioned to an uncomfortable level. We preferred to go out for drinks for this reason. There are plenty of restaurants close by to choose from. On the whole we really enjoyed our stay and we’d definitely recomend."
Cynthia 2-night trip
Posted 2 hours ago
The View 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 $108 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?

Outstanding luxury beachfront holiday experience with hot tub: This vacation home rental near Winchelsea is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 selection of games and a hot tub.

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 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.