Winchelsea Holiday Rentals from AU$138: Search Short-Term Rentals

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Our top choices for Winchelsea holiday 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.

includes taxes & fees

10 Sept - 11 Sept

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

2. Sparrows Den Lodge

Winchelsea

includes taxes & fees

5 Oct - 6 Oct

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

3. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

includes taxes & fees

25 Sept - 26 Sept

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

4. Extraordinary Huts

Rye

Diana

includes taxes & fees

16 Sept - 17 Sept

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

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

East Sussex

Mark

includes taxes & fees

10 Sept - 11 Sept

A living room with a fireplace, a green sofa, a round ottoman, and a painting on the wall.

6. 3 Cinque Ports Street

Rye

includes taxes & fees

16 Sept - 17 Sept

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

7. Rhodown - sun on the terrace all round

Hastings

William E.

includes taxes & fees

9 Sept - 10 Sept

A traditional building with a sign for 'Swan Cottage Tea Rooms' and 'Accommodations' offering real ales and good food.

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

Rye

Robert E.

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

9. 2 bedroom accommodation in Rye

Rye

Sheila Davies

includes taxes & fees

27 Sept - 28 Sept

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

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

Rye

Kerry

includes taxes & fees

10 Sept - 11 Sept

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

11. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

includes taxes & fees

21 Sept - 22 Sept

A two-story brick house with a visible front door, a small porch, and a fenced yard.

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

Playden, Rye

Edward W.

includes taxes & fees

15 Sept - 16 Sept

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

13. 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.

includes taxes & fees

8 Oct - 9 Oct

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

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

Rye

Anonymous traveller

includes taxes & fees

11 Sept - 12 Sept

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

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.

includes taxes & fees

9 Sept - 10 Sept

A cozy living room with a sofa, a dining table set for two, and a small side table.

16. 1A Coastguard Cottages

Rye

includes taxes & fees

27 Sept - 28 Sept

A dining area with a table set for a meal, surrounded by bookshelves and a television.

17. 4 bedroom accommodation in Pett

Pett

Sarah Gunner

includes taxes & fees

17 Sept - 18 Sept

A modern building with a curved facade, multiple balconies, and a grassy area in front.

18. Bexlet

Bexhill-on-Sea

Tim

includes taxes & fees

28 Sept - 29 Sept

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

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

Camber

includes taxes & fees

5 Oct - 6 Oct

20. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

includes taxes & fees

28 Sept - 29 Sept

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Top Winchelsea Hotel Reviews

The Burlington Hotel

8/10 Good

"Hotel staff we very nice and reception wer very polite &helpful, Very old building that understandably needs a lot of work , but the main thing that let's it down is the bedrooms, our room (237) The carpet was shocking so stained! Really in need of a new one, the stair carpet needed a good hoover! Breakfast was good,"

The Grand Hotel Eastbourne

8/10 Good

"Beautiful building, lobby and dining area. Excellent spot too, just across the road from the beach and a great French restaurant and also walking distance to the pier. Rooms look a little tired and could do with a refresh. Bath tub and carpet had stains, mattress was way too soft and door squeaked at night due to a draft from the windows which made it difficult to sleep. A bit of repainting and refresh of the room interior would make it outstanding. Pool was very nice but can get overcrowded. Staff overall were very friendly and breakfast was nice. Early check in was also appreciated since we had a toddler with us."

The George in Rye

10/10 Excellent

"It was such a charming and lovely hotel. My friend and I each booked our own room. The rooms were spacious and had bathtubs, so we were able to relax and unwind. The staff were always very kind and helpful. There were also plenty of great restaurants and cafés within walking distance. It was the perfect place for a short getaway."

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."

Find out more about Winchelsea

Everything you need to know about Winchelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winchelsea holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchelsea holiday rentals we have selected for you start as low as AU$138 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchelsea rentals

At Expedia, we put the best Winchelsea holiday 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 holiday.

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 holiday rentals in Winchelsea?

Yes, there are holiday rentals close to the most popular sights in Winchelsea, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchelsea has a good selection of restaurants. Make sure you have time to check out the breweries and gardens during your trip.

What are some of the best holiday rentals that Winchelsea has to offer?

Fabulous 5 bed house with indoor swimming pool and hot tub in 1066 Country: This holiday home rental outside of 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 holiday with a garden and 1 hot tub.

How many holiday rentals are there in Winchelsea?

With 14 Expedia holiday rentals, you're guaranteed 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 holiday rental in Winchelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchelsea. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.

Winchelsea Holiday Rentals

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Check prices for these dates

Our top choices for Winchelsea holiday rentals

1. White Haven - with 2 double rooms

2. Sparrows Den Lodge

3. 1 bedroom accommodation in Winchelsea Beach, near Rye

4. Extraordinary Huts

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

6. 3 Cinque Ports Street

7. Rhodown - sun on the terrace all round

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

9. 2 bedroom accommodation in Rye

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

11. Chestnut Meadow Camping

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

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

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

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

16. 1A Coastguard Cottages

17. 4 bedroom accommodation in Pett

18. Bexlet

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

20. Cabin - Sleeps 8 - Garden and Parking

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

The Burlington Hotel

Find out more about Winchelsea

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