Holiday Rentals Winchelsea from ฿3,268: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Winchelsea holiday rentals

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

1. Sparrows Den Lodge

Winchelsea

฿18,166 total

includes taxes & fees

19 Oct - 20 Oct

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

2. Extraordinary Huts

Rye

Diana

฿6,762 total

includes taxes & fees

22 Oct - 23 Oct

A row of white houses with brown roofs and a sandy beach in the foreground.

3. 16 The Boathouse

Rye

Andrew

฿17,713 total

includes taxes & fees

4 Nov - 5 Nov

A hotel room with a bed, two armchairs, a small round table with a vase of flowers, and a view of the outdoors through large windows with curtains.

4. Osborne Apartments

Eastbourne

Melvyn Spencer

฿3,268 total

includes taxes & fees

21 Oct - 22 Oct

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

5. 1 Bed - Sleeps 2 - Near Beach - Parking

Hastings

Stephen

฿5,203 total

includes taxes & fees

29 Oct - 30 Oct

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

6. Chestnut Meadow Camping

Bexhill-on-Sea

Mary

฿3,333 total

includes taxes & fees

16 Oct - 17 Oct

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

7. Bexlet

Bexhill-on-Sea

Tim

฿3,509 total

includes taxes & fees

2 Nov - 3 Nov

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

8. Pinewood Camping Pods - At Port Lympne Reserve

Hythe

Lesley

฿6,418 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a sectional sofa, a fireplace, and a TV mounted on the wall.

9. The Pigsty at the Secret Garden

Ashford

฿12,014 total

includes taxes & fees

12 Nov - 13 Nov

A wooden deck with a striped cushion, a brick wall, and a view of a river.

10. 7 Waves

Rye

฿18,483 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Rye

Kerry

฿6,951 total

includes taxes & fees

12 Nov - 13 Nov

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

12. 3 Cinque Ports Street

Rye

฿18,982 total

includes taxes & fees

19 Oct - 20 Oct

A wooden cabin room with a bed, a TV mounted on the wall, and a door leading outside.

13. Pet Friendly Private Cabin Town Eurotunnel Beach

Hythe

David

฿3,311 total

includes taxes & fees

13 Nov - 14 Nov

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

14. 17 The Boathouse

Rye

Tony

฿18,212 total

includes taxes & fees

6 Nov - 7 Nov

A living room with a sofa, coffee table, and a fireplace.

15. Suspire House -sleeps6-garden-bbq-coastal Retreat

New Romney

"We left after just 4 hours because the property was nothing like the listing. The photos give a far better impression than the reality. Before arrival, I had to chase the host for check-in instructions as nothing had been sent. Even after calling, I was only given the key safe code. Later that day, after we’d already left, I received an email stating there was a £100 charge per pet, despite the Hotels.com listing clearly advertising “pets go free.” The property appeared to have had only...

Werner

฿9,700 total

includes taxes & fees

15 Nov - 16 Nov

A narrow cobblestone path flanked by a brick house with a black metal fence, leading to a tree-lined street.

16. Lantern Cottage

Rye

฿20,296 total

includes taxes & fees

2 Nov - 3 Nov

A bench overlooking a coastal view with a clear sky and a distant shoreline.

17. 2-bed, Sleeps 4, Free Parking, Pets Allowed

Eastbourne City Centre

฿9,476 total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, bedside table, nightstand, and a ceiling light fixture.

18. Summerhill by Suspire

Ashford

฿9,747 total

includes taxes & fees

18 Oct - 19 Oct

A cozy room with a brick fireplace, blue sofas, a wooden coffee table, and a guitar.

19. Summerhill Manor Retreat - 7 Bedroom House

Ashford

฿61,558 total

includes taxes & fees

22 Oct - 23 Oct

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

20. 1A Coastguard Cottages

Rye

฿22,289 total

includes taxes & fees

24 Oct - 25 Oct

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Top Winchelsea Hotel Reviews

Majestic Hotel Eastbourne by Belvilla

10/10 Excellent

"Really pleased with my stay at The Majestic. The room was spacious, clean and had everything I needed, including great WiFi, a smart TV and tea and coffee facilities. The bed was very comfortable and the sea views were beautiful. Check-in was simple and hassle-free, and the whole stay was relaxing and enjoyable. I'd be happy to return in the future."

The Lookout Rye

8/10 Good

"As there had been a number of poor reviews recently it was with trepidation that we arrived in Rye Check in was quick and straightforward with helpful smiling staff Car was parked in the Hotel car park at a cost of £10 via Ringo app which although more expensive than any other car park in Rye had the convenience of being at the hotel The Hotel is looking tired and would benefit with a complete external refurb (as are many hotels in present climate), however the Rooms were clean, excellent walk in shower in spacious bathroom with excellent daily maintenance service Bed was very comfortable and room included coffee, tea (various varieties) and biscuits all topped up daily along with the large bottle of water Situated at the top of the town, whilst not offering a restaurant there are plenty of eateries/bars within a 10 min walk Breakfast is excellent including a continental, fruit, cereals, pastries as well as cooked breakfast to order This is the sister hotel to the well known George Hotel, 400 yards down the road and having stayed in both I have to admit the Lookout gives much better value and the room I had was better than that given at the George Although staff kept to a minimum all are helpful and cheerful"

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)"

The Chatsworth Hotel

10/10 Excellent

"Visiting a relative in Eastbourne, we booked the hotel based on its reviews, and we are so glad we did. With a great position, right on the sea front, with just a short walk to shops and restaurants. A beautiful building, built at the turn of the 20th century it had been completely refurbished, and re-opened in 2019. They have skilfully kept the best things, the 125 year old cage lift, the beautiful downstairs windows and other architectural details, whilst modernising the property in keeping with the original style. We loved the piano bar and the guest lounge. Our room on the top floor has a sea view, a very comfortable bed, coffee machine and tea-making facilities. The bathroom was ideal, with the walk-in shower we had requested. They provided a hairdryer although I had taken my own. The only slight irritation was that, like so many other hotels, there was no mirror anywhere near a plug to see how you were drying your hair. Parking was available across the road and the hotel provided the necessary parking permit at a very reasonable cost, Very friendly staff and spotlessly clean. A wonderful hotel that we will use again."

Find out more about Winchelsea

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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.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchelsea holiday rentals

1. Sparrows Den Lodge

2. Extraordinary Huts

3. 16 The Boathouse

4. Osborne Apartments

5. 1 Bed - Sleeps 2 - Near Beach - Parking

6. Chestnut Meadow Camping

7. Bexlet

8. Pinewood Camping Pods - At Port Lympne Reserve

9. The Pigsty at the Secret Garden

10. 7 Waves

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

12. 3 Cinque Ports Street

13. Pet Friendly Private Cabin Town Eurotunnel Beach

14. 17 The Boathouse

15. Suspire House -sleeps6-garden-bbq-coastal Retreat

16. Lantern Cottage

17. 2-bed, Sleeps 4, Free Parking, Pets Allowed

18. Summerhill by Suspire

19. Summerhill Manor Retreat - 7 Bedroom House

20. 1A Coastguard Cottages

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

Majestic Hotel Eastbourne by Belvilla

The Lookout Rye

Hythe Imperial Hotel Spa & Golf

The Grand Hotel Eastbourne

The Relais Cooden Beach

Flackley Ash Country House Hotel

The Chatsworth Hotel

The Cumberland Hotel

Find out more about Winchelsea

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in Winchelsea

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchelsea holiday rentals

1. Sparrows Den Lodge

2. Extraordinary Huts

3. 16 The Boathouse

4. Osborne Apartments

5. 1 Bed - Sleeps 2 - Near Beach - Parking

6. Chestnut Meadow Camping

7. Bexlet

8. Pinewood Camping Pods - At Port Lympne Reserve

9. The Pigsty at the Secret Garden

10. 7 Waves

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

12. 3 Cinque Ports Street

13. Pet Friendly Private Cabin Town Eurotunnel Beach

14. 17 The Boathouse

15. Suspire House -sleeps6-garden-bbq-coastal Retreat

16. Lantern Cottage

17. 2-bed, Sleeps 4, Free Parking, Pets Allowed

18. Summerhill by Suspire

19. Summerhill Manor Retreat - 7 Bedroom House

20. 1A Coastguard Cottages

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

Majestic Hotel Eastbourne by Belvilla

Find out more about Winchelsea

Frequently asked questions

Go further with the Expedia app