Holiday Rentals Winchelsea from ₹7,776: Find Short-Term Rentals & Holiday Accommodations

A stone archway leading to a road, surrounded by residential houses and a stone wall.

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Our top choices for Winchelsea holiday rentals

A beach with pebbles and a person in the water.

1. Sparrows Den Lodge

Winchelsea

₹55,852 total

includes taxes & fees

26 Nov - 27 Nov

A small, green wooden cabin with a balcony, surrounded by trees and purple flowers.

2. Extraordinary Huts

Rye

Karen

₹18,744 total

includes taxes & fees

16 Nov - 17 Nov

A brick wall with a stone base, a wooden gate, and two planters with soil.

3. 3 Cinque Ports Street

Rye

₹58,359 total

includes taxes & fees

16 Nov - 17 Nov

A beach with a person and a dog walking along the shore.

4. 3-bed Camber Sands Cabin - Pool - Parking - Pets

Rye

₹29,802 total

includes taxes & fees

22 Nov - 23 Nov

A hotel room with a bed, a sofa, a table with a vase of flowers, and large windows with curtains.

5. Osborne Apartments

Eastbourne

Melvyn Spencer

₹7,688 total

includes taxes & fees

14 Dec - 15 Dec

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

₹9,332 total

includes taxes & fees

14 Nov - 15 Nov

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

7. Bexlet

Bexhill-on-Sea

Clive

₹9,824 total

includes taxes & fees

22 Nov - 23 Nov

Two wooden dome-shaped cabins with wooden railings and a deck, surrounded by trees.

8. Pinewood Camping Pods - At Port Lympne Reserve

Hythe

Lesley

₹20,491 total

includes taxes & fees

23 Nov - 24 Nov

9. Spacious Private Annex Near Ashford

Ashford

Liliana

₹12,367 total

includes taxes & fees

17 Nov - 18 Nov

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

10. 17 The Boathouse

Rye

Tony

₹50,992 total

includes taxes & fees

26 Nov - 27 Nov

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

11. 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

₹26,948 total

includes taxes & fees

16 Nov - 17 Nov

A view through a window with hanging fish decorations.

12. Rye House

Rye

A small, single-story house with a patio area featuring a table and chairs.

13. Pet Friendly Private Cabin Town Eurotunnel Beach

Hythe

David

₹9,271 total

includes taxes & fees

29 Nov - 30 Nov

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

14. Lantern Cottage

Rye

Gillian

₹62,399 total

includes taxes & fees

16 Nov - 17 Nov

A two-story brick house with a gravel driveway and a small garden.

15. Summerhill by Suspire

Ashford

₹27,079 total

includes taxes & fees

14 Nov - 15 Nov

A waterfront property with multiple buildings, a dock, and a gravel path.

16. 7 Waves

Rye

₹56,827 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Rye

Kerry

₹17,880 total

includes taxes & fees

18 Nov - 19 Nov

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

18. 2-bed, Sleeps 4, Free Parking, Pets Allowed

Eastbourne City Centre

A cozy living room with a piano, a white armchair, a fireplace, and a clock on the wall.

19. Summerhill Manor Retreat - 7 Bedroom House

Ashford

₹170,773 total

includes taxes & fees

14 Nov - 15 Nov

A mobile home with a fenced porch, a window, and a door.

20. Cabin - Sleeps 8 - Garden and Parking

St Leonards-On-Sea

₹25,840 total

includes taxes & fees

14 Nov - 15 Nov

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Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

The New Inn

Winchelsea

10/10 Excellent

We stayed for one night at The New Inn. A lovely quiet location and such a warm welcome with an open log fire burning as we arrived and lovely friendly staff. We ate downstairs in the evening and the food was both delicious and great value. The full English breakfast was fabulous - my husband said the best he has had for as long as he could remember so compliments to the chef!! We will definitely stay again when next in the area.

Sandra D

A traditional brick building with a white facade, a small attached structure, and a paved area with benches.

The Hope Anchor

Rye

10/10 Excellent

John

A rustic dining area with wooden tables and chairs, string lights on the ceiling, and a brick wall.

The Ship Inn

Rye

10/10 Excellent

I was really pleased with the Ship,vand a couple of other reviews didn't do it credit at all, in fact I thought the reviewer must have stayed at a different place . It was a last minute business trip, one night stay and the price and location were really good. I had booked a deluxe double but my meeting was called forward by one day so I had to rebook through here and only a standard was available that night, that having been said the room was fine. Yes, it is a 16th Century Inn so the rooms...

Mark

A room with a wooden chair, a large mirror, and a bathtub.

The George in Rye

Rye

10/10 Excellent

Stayed for one night at the George in Rye. Right in the centre of town and convenient for browsing the local shops. Stayed in Room 3 which was absolutely gorgeous. The general décor of the hotel is beautiful and the staff were very pleasant and helpful. Had our evening meal there - quite pricey but enjoyable with good service. Breakfast (included in room price) was equally enjoyable but no sign of any toast! I'm sure if we'd asked it would have been provided though. Only downside was no...

Sharon

A bar area with a wooden counter, hanging lights, and a potted plant.

River Haven Hotel

Rye

10/10 Excellent

Susan

A dining area with wooden tables and chairs, a kitchen area with cabinets, and a hallway leading to another room.

The Old Borough Arms

Rye

10/10 Excellent

The staff were very welcoming,friendly and served a delicious Vegetarian Breakfast in record time.Rye is a delightful place with lots to see, do,and places to eat and drink.Not to mention the lovely array of independent shops.I would certainly return to the Old Borough arms as I loved the relaxed feel and having your own key to come and go as you please was a real bonus.Far preferable to staying in a hotel,although it had that hotel air about it with a proper iron and board,tea and coffee making...

Gilly

Extraordinary Huts

Rye

10/10 Excellent

Anonymous traveller

A hotel room with a large bed, a chair, a table with a lamp, and a window with curtains.

The Lookout Rye

Rye

10/10 Excellent

Great hotel and location for centre of Rye and its surrounding attractions via the bus station - 313 bus to Rye Harbour, 10 minutes and Stop B for Camber Sands, 15 minutes. Hotel was lovely and staff friendly and helpful. Room No1 was very spacious for 2. Great tea/coffee facilities, hairdryer and ironing board/iron if you so wished. The room itself needed updating and redecorating and the curtain was torn. The furniture was damaged and dated. The dressing gowns and cushions needed a dry clean...

Devika

A large, two-story brick building with a symmetrical facade, multiple windows, and a gravel driveway.

Flackley Ash Country House Hotel

Rye

10/10 Excellent

ABSOLUTELY BRILLIANT ! I cannot fault this hotel in ANY way - we stayed for 2 nights ( having done a day trip to France via the Euro Tunnel ) and absolutely LOVED it ! ( and would most DEFINITELY come back again ) The indoor swimming pool and whirlpool were AMAZING, as was the breakfast ! - ALL you could possibly want ASWELL I as a cooked English ! What more could you ask for ? If you were to ask me to sum this hotel up in 1 word it would be - PERFECT !

Anonymous traveller

A cozy lounge area with leather sofas, a brick fireplace, and framed pictures on the wall.

The Kings Head Rye

Rye

10/10 Excellent

Ann

A cozy room with a bed, a sofa, a small table, a fireplace, and a window with curtains.

The Woolpack Inn Warehorne

Ashford

10/10 Excellent

John

A spacious lounge area with multiple seating options, including sofas and chairs, and a dining area with tables and chairs.

Moore House

Old Town Hastings

10/10 Excellent

Birute

A dining area with a table set for two, large windows offering a view of a town with houses and a hill in the background.

The Laindons

Old Town Hastings

10/10 Excellent

Norman

A bedroom with a large bed, wooden beams on the ceiling, a dresser, and a desk with a lamp.

Little Dane Court

Tenterden

10/10 Excellent

Lisa

Find out more about Winchelsea

Holiday Rentals in Winchelsea

Search for holiday rentals in Winchelsea on Expedia.co.uk! 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.

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.

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. 3 Cinque Ports Street

4. 3-bed Camber Sands Cabin - Pool - Parking - Pets

5. Osborne Apartments

6. Chestnut Meadow Camping

7. Bexlet

8. Pinewood Camping Pods - At Port Lympne Reserve

9. Spacious Private Annex Near Ashford

10. 17 The Boathouse

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

12. Rye House

13. Pet Friendly Private Cabin Town Eurotunnel Beach

14. Lantern Cottage

15. Summerhill by Suspire

16. 7 Waves

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

18. 2-bed, Sleeps 4, Free Parking, Pets Allowed

19. Summerhill Manor Retreat - 7 Bedroom House

20. Cabin - Sleeps 8 - Garden and Parking

Find holiday rentals that suit your style

Top Winchelsea Hotel Reviews

The New Inn

10/10 Excellent

Find out more about Winchelsea

Holiday Rentals in Winchelsea

Frequently Asked Questions

Can I find holiday rentals in Winchelsea?

How many holiday rentals are there in Winchelsea?

What’s there to see and do in Winchelsea?

What’s a holiday rental in Winchelsea like?