Winchelsea Vacation Rentals from $39: Search Short-Term Rentals

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Our top choices for Winchelsea vacation rentals

A mobile home with a white exterior, a covered porch, and a number 27 sign.

1. White Haven - with 2 double rooms

Winchelsea Beach

"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...

Emma V.

$293 nightly

Oct 19 - Oct 20

Total with taxes and fees

A brick house with a small patio, a white door, and a wooden fence.

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

$350 nightly

Nov 6 - Nov 7

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

3. Sparrows Den Lodge

Winchelsea

$454 nightly

Oct 22 - Oct 23

Total with taxes and fees

A cozy interior with a wood-burning stove, a kitchen area, a sofa, and a view of the outdoors.

4. Extraordinary Huts

Rye

Diana

$174 nightly

Oct 22 - Oct 23

Total with taxes and fees

A dining area with a green staircase, a glass table, and chairs.

5. 3 Cinque Ports Street

Rye

$475 nightly

Oct 21 - Oct 22

Total with taxes and fees

A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

6. An unusual two-storey apartment with beams and an open fire.

Rye

Robert E.

$263 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a bed, a chair, a wooden table, and a potted plant.

7. 1 Bed - Sleeps 2 - Near Beach - Parking

Hastings

Stephen

$130 nightly

Oct 21 - Oct 22

Total with taxes and fees

A cozy bedroom with a wooden headboard, a bed with patterned pillows, bedside lamps, and a decorative sign on the wall.

8. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

East Sussex

Alyson B.

$191 nightly

Oct 20 - Oct 21

Total with taxes and fees

A greenhouse structure surrounded by yellow flowering plants.

9. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

Rye

"A little gem nestled in the countryside with glorious views. Lucy’s apartment was spotlessly clean and tidy, comfortable and very well equipped. Lucy is an absolute hoot- very welcoming and full of suggestions of things to see or do. Perfect for dogs too, with a lovely enclosed garden and lots of walks from the location detailed in the information folder. Lots of lovely pubs nearby too including a local just across the way. We would definitely come back."

Kerry H.

$190 nightly

Oct 19 - Oct 20

Total with taxes and fees

A wooden staircase leading to a backyard with a garden, a small shed, and a house with a sloped roof.

10. 2 bedroom accommodation in Rye

Rye

Sheila Davies

$249 nightly

Nov 8 - Nov 9

Total with taxes and fees

A room with a fireplace, a desk, a chair, and a large window with a view of greenery.

11. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

Hastings

"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...

Tabassum A.

$467 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a dining area with a table set for four.

12. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

Camber Rye

"Such a beautiful caravan. We went at Easter 2026 and there were beautiful Easter touches bunnies etc throughout the caravan. Chocolates and Proscecco were a lovely touch. Checking in process was seamless and they provided so much helpful information. Would recommend and will definitely be back for another stay. Dog friendly too, my dogs loved the warm cozy throws provided and enclosed gated decking area"

Claire O.

$211 nightly

Oct 19 - Oct 20

Total with taxes and fees

A secluded outdoor area with two small, semi-circular wooden structures, surrounded by lush greenery and trees.

13. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

$83 nightly

Oct 19 - Oct 20

Total with taxes and fees

A river with a boat, surrounded by greenery and buildings.

14. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Hastings

Melanie G.

$216 nightly

Nov 1 - Nov 2

Total with taxes and fees

A row of white houses with red roofs by a calm water body, boats docked, and a red sign in the foreground.

15. 17 The Boathouse

Rye

Tony

$455 nightly

Nov 6 - Nov 7

Total with taxes and fees

A modern bedroom with a large bed, a bedside table, a desk, and a window.

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

Rye

Anonymous traveler

$271 nightly

Oct 20 - Oct 21

Total with taxes and fees

A compact kitchen with a stove, oven, sink, and wooden countertops.

17. Caravan With Decking&patio-8/10 Berth-pet Friendly

Rye

Kerry

$203 nightly

Nov 4 - Nov 5

Total with taxes and fees

A modern living room with a grey sofa, a wooden coffee table, a TV on a stand, and light blue curtains.

18. Rhodown - sun on the terrace all round

Hastings

William E.

$309 nightly

Oct 19 - Oct 20

Total with taxes and fees

A cozy living room with a sofa, a white furry chair, a wooden table, and a fireplace.

19. Pinewood Camping Pods - At Port Lympne Reserve

Hythe

Lesley

$160 nightly

Nov 2 - Nov 3

Total with taxes and fees

A compact living space with a kitchenette, dining area, and seating area.

20. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Camber

$251 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Top Winchelsea Hotel Reviews

Hampton by Hilton Ashford International

8/10 Good

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The Chatsworth Hotel

10/10 Excellent

"We had a fabulous albeit brief stay at the Chatsworth Hotel. Our room was vey clean & pspacious with a balcony that faced the sea . It was lovely to hear the sea whilst drifting off to sleep in the super comfy bed. We will defintely return and dine in as the menu looked lovely . We enjoyed a drink in the bar whilst listening to some live music . All the employees were super friendly ."

Hythe Imperial Hotel Spa & Golf

10/10 Excellent

"This was our second stay , this time for 2 nights. A warm friendly welcome at reception,quickly booked in and up too our room's. Good well appointed room , clean and comfy. Good food and service in the Martello bar. A great base for visiting Port Lympne animal park and exploring the local area with the added bonus of being a short walk to the seafront and Hythe Town centre."

Flackley Ash Country House Hotel

10/10 Excellent

"Country house hotel set in beautiful grounds at Peasmarsh near Rye. We enjoyed our stay despite heavy rain. Cosy room looking out on lawn with bath, kettle (tea and coffee etc). Good WiFi. TV with Freeview. Very nice Pool, sauna and Jacuzzi. We did not eat at the hotel but did enjoy drinks in the comfortable bar. Ample parking. A hotel set in the country - good for exploring Rye, walking in the country and visiting Vineyards (Tillingham vineyard is close)"

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 $39 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.

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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?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This vacation home rental near Winchelsea offers an indoor pool, a patio, and laundry facilities to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Winchelsea?

With 14 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.

Winchelsea Vacation Rentals

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Check prices for these dates

Our top choices for Winchelsea vacation rentals

1. White Haven - with 2 double rooms

2. 1 bedroom accommodation in Winchelsea Beach, near Rye

3. Sparrows Den Lodge

4. Extraordinary Huts

5. 3 Cinque Ports Street

6. An unusual two-storey apartment with beams and an open fire.

7. 1 Bed - Sleeps 2 - Near Beach - Parking

8. Private Quiet Cabin, overlooking Paddocks Vineyards and Pine Forest

9. A Self-Contained Private First Floor One Bedroom Annexe with Garden close to Rye

10. 2 bedroom accommodation in Rye

11. Huge Coastal House | Sleeps 16 | Beach, Old Town & Country Park | 10 beds

12. Big Boss Caravan-Camber Sands,Sleep 8, Free Wi-Fi, Netflix, Parking

13. Chestnut Meadow Camping

14. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

15. 17 The Boathouse

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

17. Caravan With Decking&patio-8/10 Berth-pet Friendly

18. Rhodown - sun on the terrace all round

19. Pinewood Camping Pods - At Port Lympne Reserve

20. Cosy and spacious 8 berth caravan in Camber Sands. Pet friendly!

Find vacation rentals that suit your style

Top Winchelsea Hotel Reviews

Hampton by Hilton Ashford International

Find out more about Winchelsea

Explore a world of travel with Expedia

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