Winchelsea Vacation Rentals from $61: Search Short-Term Rentals

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Our top choices for Winchelsea vacation rentals

1. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

$437 nightly

Sep 25 - Sep 26

Total with taxes and fees

2. Sparrows Den Lodge

Winchelsea

$461 nightly

Sep 6 - Sep 7

Total with taxes and fees

3. 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.

$297 nightly

Sep 3 - Sep 4

Total with taxes and fees

4. Extraordinary Huts

Rye

Diana

$189 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. 3 Cinque Ports Street

Rye

$481 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

Rye

Robert E.

$315 nightly

Sep 6 - Sep 7

Total with taxes and fees

7. 2 bedroom accommodation in Rye

Rye

Sheila Davies

$315 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. 4 bedroom accommodation in Pett

Pett

Sarah Gunner

$685 nightly

Sep 10 - Sep 11

Total with taxes and fees

9. Charming 3-bedroom house in soothing Playden Rye neighborhood

Playden, Rye

Edward W.

$446 nightly

Sep 3 - Sep 4

Total with taxes and fees

10. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

$185 nightly

Sep 28 - Sep 29

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi (free), bed sheets

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

East Sussex

Mark

$194 nightly

Sep 3 - Sep 4

Total with taxes and fees

12. Oastbrook Glamping

Robertsbridge

Sima

$214 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Rye

Anonymous traveler

$275 nightly

Sep 30 - Oct 1

Total with taxes and fees

14. Rye House

Rye

$565 nightly

Sep 22 - Sep 23

Total with taxes and fees

15. 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.

$265 nightly

Sep 3 - Sep 4

Total with taxes and fees

16. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Hastings

Melanie G.

$264 nightly

Sep 13 - Sep 14

Total with taxes and fees

17. Rhodown - sun on the terrace all round

Hastings

William E.

$314 nightly

Sep 3 - Sep 4

Total with taxes and fees

18. 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.

$484 nightly

Sep 6 - Sep 7

Total with taxes and fees

19. 2 bedroom accommodation in Lydd, Romney Marsh

Lydd, Romney Marsh

Stephen Docherty

$450 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Rye

Kerry

$237 nightly

Sep 4 - Sep 5

Total with taxes and fees

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Top Winchelsea Hotel Reviews

Ashford International Hotel & Spa

10/10 Excellent

"Absolutely perfect stay. Staff all amazing. From reception to spa and breakfast. Swimming pool lovely. Ample, secure parking and comfy, quiet rooms. Perfect for an overnight stay before the shuttle or ferry. Will be here again. Also very close to M&S and huge sainsbury if ypu need anything or petrol in the morning. Cannot recommended enough, we will be back."

The Burlington Hotel

8/10 Good

"The room was a very generous size for a twin room. It was neat and tidy. The beds were fine, comfortable and nice size. The bathroom was also a very generous size. The shower wasn’t great (on the fourth floor - maybe not great pressure). Nice the easiest to wash hair but not too much of an issue with just a two night stay. Room entry was a physical key, which unfortunately kept getting stuck in the lock. The furniture in the room was very nice and quite spacious and in good condition. The furniture in one of the lounge areas was not so good with cracked leather and one with a throw on to cover the damage. It didn’t bother us but I can see that some people may not be happy with that. The atmosphere was relaxed. The reception staff were very helpful and friendly, giving lots of information. The bar staff were also very helpful and friendly. The restaurant was lovely. We ate from the restaurant menu (3 courses for a set price) both nights. The food was amazing, we were very impressed. The waiting staff were great and the speed of service was very good. It was our first stay at the hotel but agree that we would be happy to stay again - preferably when the large lift is fixed. There was only a small lift working but realistically you can only get two people in without suitcases."

Cavendish Hotel

8/10 Good

"It's a grand old building - and some of the public areas downstairs are nicely done, and look great. Big and spacious reception/foyer and bar area as well (Didn't use the restaurant). The room was a good size, and a decent price - but as wih many of these big, old properties, it's worn & tired. It was cleaned well, and plenty of space."

The Lookout Rye

10/10 Excellent

"We stayed here for one night. The hotel was lovely and perfectly appointed. It was close to the bars and restaurants,a couple of minutes walk and you’re in the centre of Rye so if you come by train it’s easy to walk to the hotel and to everything around it. The bedroom was clean and comfortable. We had breakfast which was really good. The staff were really friendly. We couldn’t fault anything about it for the time we were there."

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 $61 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?

Converted barn / Oast House with amazing views and EV chargers: This vacation home rental near Winchelsea is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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. 1 bedroom accommodation in Winchelsea Beach, near Rye

2. Sparrows Den Lodge

3. White Haven - with 2 double rooms

4. Extraordinary Huts

5. 3 Cinque Ports Street

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

7. 2 bedroom accommodation in Rye

8. 4 bedroom accommodation in Pett

9. Charming 3-bedroom house in soothing Playden Rye neighborhood

10. Cabin - Sleeps 8 - Garden and Parking

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

12. Oastbrook Glamping

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

14. Rye House

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

16. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

17. Rhodown - sun on the terrace all round

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

19. 2 bedroom accommodation in Lydd, Romney Marsh

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

Find vacation rentals that suit your style

Top Winchelsea Hotel Reviews

Ashford International Hotel & Spa

Find out more about Winchelsea

Explore a world of travel with Expedia

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