Winchelsea Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Winchelsea holiday rentals

1. 1 bedroom accommodation in Winchelsea Beach, near Rye

Winchelsea Beach, near Rye

Emma Martin-Smith

HK$3,326 total

includes taxes & fees

25 Sept - 26 Sept

2. Sparrows Den Lodge

Winchelsea

HK$4,334 total

includes taxes & fees

5 Oct - 6 Oct

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.

HK$2,331 total

includes taxes & fees

14 Sept - 15 Sept

4. Extraordinary Huts

Rye

Diana

HK$1,613 total

includes taxes & fees

12 Oct - 13 Oct

5. 3 Cinque Ports Street

Rye

HK$4,528 total

includes taxes & fees

16 Sept - 17 Sept

6. 4 bedroom accommodation in Pett

Pett

Sarah Gunner

HK$5,372 total

includes taxes & fees

17 Sept - 18 Sept

7. 2 bedroom accommodation in Rye

Rye

Sheila Davies

HK$2,469 total

includes taxes & fees

20 Sept - 21 Sept

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

Playden, Rye

Edward W.

HK$3,507 total

includes taxes & fees

13 Sept - 14 Sept

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

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

East Sussex

Mark

HK$1,517 total

includes taxes & fees

21 Sept - 22 Sept

10. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

HK$1,759 total

includes taxes & fees

28 Sept - 29 Sept

11. Oastbrook Glamping

Robertsbridge

Sima

HK$2,013 total

includes taxes & fees

13 Sept - 14 Sept

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

Rye

Anonymous traveller

HK$2,154 total

includes taxes & fees

6 Oct - 7 Oct

13. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

Hastings

Melanie G.

HK$2,077 total

includes taxes & fees

13 Sept - 14 Sept

14. 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.

HK$2,098 total

includes taxes & fees

1 Oct - 2 Oct

15. 1A Coastguard Cottages

Rye

HK$5,317 total

includes taxes & fees

19 Sept - 20 Sept

Coffee/tea maker, fridge, microwave, oven

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

Camber

HK$2,155 total

includes taxes & fees

6 Oct - 7 Oct

17. Rhodown - sun on the terrace all round

Hastings

William E.

HK$2,458 total

includes taxes & fees

12 Sept - 13 Sept

18. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

HK$795 total

includes taxes & fees

13 Sept - 14 Sept

19. 2 bedroom accommodation in Lydd, Romney Marsh

Lydd, Romney Marsh

Stephen Docherty

HK$3,528 total

includes taxes & fees

24 Sept - 25 Sept

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

Rye

Kerry

HK$1,871 total

includes taxes & fees

13 Sept - 14 Sept

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Top Winchelsea Hotel Reviews

The View Hotel

10/10 Excellent

"We liked everything staff,room,food,location, all excellent"

The Lookout Rye

8/10 Good

"Clean room and comfy bed. Staff helpful and excellent breakfast in sunny location with lovely view. No evening food available, but good choice of local restaurants in Rye. Bathroom was outdated and in need of refresh, but ok to use with plenty of hot water and powerful shower. Outside of hotel also in need of revamp. Parked on site without issue paying £10 a day via Ringo app."

The Grand Hotel Eastbourne

8/10 Good

"The Grand Hotel is a long-established, traditional hotel with a distinctly classic look and feel. The aesthetic is not quite my personal preference, but I had a good stay and was particularly impressed by the service. I emailed the hotel before arriving and received a prompt and helpful response. My room was spacious, with generous wardrobe space, a safe, a Nespresso machine with pods, two complimentary bottles of water and bespoke bathroom amenities. Service throughout my stay was excellent. Rita and Sylvia at reception were both extremely helpful, as was the valet team. Room service occasionally took a few attempts to reach, but once through, they were attentive and the food arrived promptly. I also overslept one morning and nearly missed breakfast. They kindly arranged a tray and brought it to my room. The food was consistently excellent. The hotel has a beautiful seafront setting, especially on a clear day and the lounge and afternoon tea are clearly popular with local guests. If you favour traditional grand hotels, classic interiors and attentive service, The Grand should suit you well. For me, the quality of the service was what made the stay."

Ashford International Hotel & Spa

8/10 Good

"I really enjoyed my stay at the Ashford International Hotel. The staff were incredibly helpful and friendly, and the facilities were excellent. The hotel was very clean throughout, which made the stay even more comfortable. I especially loved relaxing in the foyer — it created such a calm and welcoming atmosphere. Overall, it was a relaxing and enjoyable stay, and I would definitely stay there again.!"

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

Search for holiday rentals in Winchelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchelsea using one of the methods below:

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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.

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Check prices for these dates

Our top choices for Winchelsea holiday 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. 4 bedroom accommodation in Pett

7. 2 bedroom accommodation in Rye

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

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

10. Cabin - Sleeps 8 - Garden and Parking

11. Oastbrook Glamping

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

13. Coghurst Hall Holiday Home Sleeps 6, 2 bedrooms

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

15. 1A Coastguard Cottages

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

17. Rhodown - sun on the terrace all round

18. Chestnut Meadow Camping

19. 2 bedroom accommodation in Lydd, Romney Marsh

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

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

The View Hotel

The Lookout Rye

Holiday Inn Ashford Central by IHG

The Chatsworth Hotel

The Grand Hotel Eastbourne

Ashford International Hotel & Spa

The George in Rye

Holiday Inn Ashford North A20 by IHG

Cavendish Hotel

Find out more about Winchelsea

Frequently asked questions

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