Winchelsea Vacation Rentals from $64: Search Short-Term Rentals

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Our top choices for Winchelsea vacation rentals

1. Grogu's Rest - 2 bedrooms with decking sleeps 6

Winchelsea Beach

lindsay r.

$330 nightly

Aug 22 - Aug 23

Total with taxes and fees

2. 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.

$298 nightly

Sep 1 - Sep 2

Total with taxes and fees

3. Sparrows Den Lodge

Winchelsea

$461 nightly

Aug 31 - Sep 1

Total with taxes and fees

4. Extraordinary Huts

Rye

Diana

$177 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

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

East Sussex

Mark

$194 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Rye

Robert E.

$315 nightly

Sep 3 - Sep 4

Total with taxes and fees

7. 1A Coastguard Cottages

Rye

$566 nightly

Aug 21 - Aug 22

Total with taxes and fees

8. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

$85 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Rye

Anonymous traveler

$275 nightly

Aug 17 - Aug 18

Total with taxes and fees

10. Caravan - Sleeps 8 - Pets Ok - Parking - Patio

Rye

Kerry

$232 nightly

Sep 2 - Sep 3

Total with taxes and fees

11. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Hastings

Melanie G.

$264 nightly

Sep 6 - Sep 7

Total with taxes and fees

12. 2 bedroom accommodation in Rye

Rye

Sheila Davies

$348 nightly

Aug 27 - Aug 28

Total with taxes and fees

13. 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 14 - Sep 15

Total with taxes and fees

14. Hillside retreat - 2 bedrooms sleeps 5

Hastings

$298 nightly

Sep 1 - Sep 2

Total with taxes and fees

15. Bexlet

Bexhill-on-Sea

Tim

$100 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

Bexhill

Mark S.

$171 nightly

Aug 21 - Aug 22

Total with taxes and fees

17. South Beach Landings 0028

Rye

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

Playden, Rye

Edward W.

$439 nightly

Aug 19 - Aug 20

Total with taxes and fees

19. Rhodown - sun on the terrace all round

Hastings

William E.

$314 nightly

Sep 1 - Sep 2

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Camber

$309 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top Winchelsea Hotel Reviews

The Grand Hotel Eastbourne

8/10 Good

"Returned again for another stay during the airbourne, unfortunately this time we noticed a few minor problems.The gentlemen out front of the hotel and stefan (from the resturant) were so helpful and welcoming! A few things we noticed during our stay this time, we came back to our room one evening towels had been taken however no new towels were left , I rung straight down stairs and they said someone would bring them up however we needed to get ready for dinner and no one brought these up , I had to then ask at reception after dinner and re ask for some towels to be left, also in the process of them removing the towels they took by mistake my microfibre hair towel which I didn’t get back. The day time we had lunch every day in the hotel however I appreciate it’s busy and there may not be enough staff but we was left way to long in between and having to keep trying to get some ones attention in which everything we order had a service charge on which in the day time I don’t think this should be the case. One evening we got to the bar just as last orders had been taken the lady behind the bar was very friendly and said she would quickly serve us , my partner and brother sat down on the chairs behind while she was making our drinks and some young man who was a worker came into the bar and said to them we’re closed you cant sit here , which we appreciate the bar was closed however I was clearly waiting for the drinks and it’s the way he said it was very rude."

The Chatsworth Hotel

10/10 Excellent

"We loved our room - Junior Suite with the biggest ever bed and fabulous view from the window overlooking the sea, with the pier to the left and the bandstand to the right. Sitting at the window became my "happy place" for our three days! The Jacuzzi bath was a nice touch but we should have asked Reception for a suction handle for the wall as there was nothing for my husband to hold onto in order to stand up and get out. The breakfasts were excellent with a good choice of hot meals cooked fresh to order. Personally I would have liked more choice of fruit but the fresh fruit on offer was adequate. The free glass of wine in the piano bar on the first night was a nice touch and we were delighted to be entertained on the piano all three nights by Annie, singing and playing (she has a beautiful voice), and Alan with his stunning playing of Jazz and Blues etc. The staff were most helpful. Thank you Chatsworth Hotel for a very enjoyable stay."

Pearl & Pebbles Eastbourne

8/10 Good

"The hotel room was spotless clean, we stayed in a quadruple room with 3 children and 2 adults. The room was a good size and two single beds in a separated room. Beds were very comfortable and they had a fan in the room. The shower didn’t have hot water and the shower curtain could do with changing. The downstairs needs full renovation but we were there for one night so good for what we used it for and the price was excellent so cheap and okey for 1 night"

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 $64 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 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.

Winchelsea Vacation Rentals

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Check prices for these dates

Our top choices for Winchelsea vacation rentals

1. Grogu's Rest - 2 bedrooms with decking sleeps 6

2. White Haven - with 2 double rooms

3. Sparrows Den Lodge

4. Extraordinary Huts

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

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

7. 1A Coastguard Cottages

8. Chestnut Meadow Camping

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

10. Caravan - Sleeps 8 - Pets Ok - Parking - Patio

11. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

12. 2 bedroom accommodation in Rye

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

14. Hillside retreat - 2 bedrooms sleeps 5

15. Bexlet

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

17. South Beach Landings 0028

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

19. Rhodown - sun on the terrace all round

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

Find vacation rentals that suit your style

Top Winchelsea Hotel Reviews

The Grand Hotel Eastbourne

Find out more about Winchelsea

Explore a world of travel with Expedia

Frequently asked questions

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