A historic church with a stone pathway leading to its entrance, surrounded by a cemetery with numerous headstones.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchelsea cottages

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

1. 1 bedroom accommodation in Winchelsea Beach, near Rye

1 bedroom accommodation in Winchelsea Beach, near Rye
Winchelsea Beach, near Rye
10.0 out of 10, Exceptional, (12 reviews)
"The Annex was lovely and clean with everything that was needed in the kitchen. We were close to shops and the beach, with the option to travel in to near by towns which weren’t too far away. Great location for our dog too as she had the freedom of the garden. Lovely place to stay and would stay here again 😊"
United States
Emma Martin-Smith
The price is AED 1,366
AED 1,366 total
includes taxes & fees
8 Nov - 9 Nov
1 bedroom accommodation in Winchelsea Beach, near Rye
A traditional building with a black and white facade, multiple windows, and a sign for 'Swan Cottage Tea Rooms'.

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

An unusual two-storey apartment with beams and an open fire.
Rye
10.0 out of 10, Exceptional, (11 reviews)
"Lovely little flat enjoyed the central location of the flat would definitely recommend "
United States
Robert E.
The price is AED 1,522
AED 1,522 total
includes taxes & fees
13 Oct - 14 Oct
An unusual two-storey apartment with beams and an open fire.
A riverside walkway with metal railings and a gravel path.

3. 17 The Boathouse

17 The Boathouse
3.0 star property
Rye
10.0 out of 10, Exceptional, (1 review)
"A lovely stay in a lovely property within walking distance of Rye town centre "
United Kingdom
Tony
The price is AED 1,659
AED 1,991 total
includes taxes & fees
6 Nov - 7 Nov
17 The Boathouse
A wooden staircase leading to a backyard with a garden, a small shed, and a house with a sloped roof.

4. 2 bedroom accommodation in Rye

2 bedroom accommodation in Rye
Rye
9.8 out of 10, Exceptional, (6 reviews)
"Very comfortable accommodation and so central to shops and restaurants. Particularly loved the wood burning stove."
United States
Sheila Davies
2 bedroom accommodation in Rye
A modern house with a dark exterior, a sloped roof, and a well-maintained garden.

5. The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom

The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful accommodation, with lovely vaulted ceiling making it bright and airy High quality finishes all round Kitchen has everything you need and a bottle of milk waiting in the fridge was a lovely touch Tea bags, coffee pods, crisps and biscuits also provided Bed was comfortable and high quality bedding Lovely big fluffy towels and M&S toiletries provided. It was so quiet at night meaning a great night sleep A lovely stay and would recommend a trip to Caster sands and Rye center"
United States
Lynn B.
The price is AED 932
AED 932 total
includes taxes & fees
21 Oct - 22 Oct
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom
A dining area with a table set for a meal, surrounded by bookshelves and a television.

6. 4 bedroom accommodation in Pett

4 bedroom accommodation in Pett
Pett
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful one night stay at Holly Cottage with family. Location is great with pubs and tearoom close by. We all commented on how comfortable the beds were and how quiet the cottage is. Would definitely recommend!"
United States
Sarah Gunner
The price is AED 2,461
AED 2,461 total
includes taxes & fees
13 Oct - 14 Oct
4 bedroom accommodation in Pett
A cozy cottage with a sloped roof, a small porch, and a well-maintained garden.

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

The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
Rye
9.8 out of 10, Exceptional, (8 reviews)
"Stayed here for a night and wish it was longer. Beautiful clean place with an extremely comfortable bed. Will definitely be back. Thankyou to the hosts x"
United States
Anonymous traveler
The price is AED 987
AED 987 total
includes taxes & fees
21 Oct - 22 Oct
The Garden Room - a holiday let that sleeps 2 guests in 1 bedroom
A wooden deck with a wooden chair and table, a blanket, and breakfast items.

8. Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom

Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
Tenterden
9.0 out of 10, Wonderful, (6 reviews)
"Great little property, surprisingly comfortable for a small space, nice rural views from the lovely hot tub, and great beer from the onsite brewery!"
United States
Harry I.
The price is AED 896
AED 896 total
includes taxes & fees
12 Oct - 13 Oct
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A two-story brick house with a white exterior, a visible chimney, and a small garden area with a potted plant.

9. 2 bedroom accommodation in Lydd, Romney Marsh

2 bedroom accommodation in Lydd, Romney Marsh
Lydd, Romney Marsh
9.4 out of 10, Exceptional, (6 reviews)
"Great communication from the owner, prior and post our stay. Very comfortable, with everything that you need. Would definitely stay again."
United States
Stephen Docherty
The price is AED 1,151
AED 1,151 total
includes taxes & fees
7 Nov - 8 Nov
2 bedroom accommodation in Lydd, Romney Marsh
A wooden house with a dark roof, a chimney, and a small front porch with steps.

10. B’s lodge at Church Elms Farm. Tennis court, games room, sleeps 4. Pet friendly

B’s lodge at Church Elms Farm. Tennis court, games room, sleeps 4. Pet friendly
Woodchurch
B’s lodge at Church Elms Farm. Tennis court, games room, sleeps 4. Pet friendly
A cobblestone street lined with traditional buildings, some with ivy and flower boxes, and street lamps.

11. Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms

Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
Benenden
9.6 out of 10, Exceptional, (20 reviews)
"A wonderful place for a holiday Nice location. Good opportunity for excursions to Hastings, Tenterden, Bodiam. Stop off at The Bull or the Milkhouse in Sissinghurst."
United States
Hartmut K.
The price is AED 3,593
AED 3,593 total
includes taxes & fees
2 Nov - 3 Nov
Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
A small brick house with a patio, a table with chairs, and a large umbrella.

12. 2 bedroom accommodation in Wadhurst, near Tunbridge Wells

2 bedroom accommodation in Wadhurst, near Tunbridge Wells
Wadhurst, near Tunbridge Wells
10.0 out of 10, Exceptional, (3 reviews)
"Once again - a fabulous stay at Hoppers Cottage . What a beautiful location ."
United States
Ian Campbell
2 bedroom accommodation in Wadhurst, near Tunbridge Wells
A white brick building with a black door, multiple windows, and a visible sign on the right side.

13. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is AED 1,729
AED 2,075 total
includes taxes & fees
17 Oct - 18 Oct
3 Cinque Ports Street
A beachside building with outdoor seating and umbrellas.

14. Stone's Throw - a holiday let that sleeps 2 guests in 1 bedroom

Stone's Throw - a holiday let that sleeps 2 guests in 1 bedroom
Hythe
10.0 out of 10, Exceptional, (3 reviews)
"This garage conversion has been thoughtfully and cleverly set up. The location is excellent for the beach and under 10 mins walk to the town’s shops and restaurants. Good and clever little kitchen set up with more than you are likely to use (e.g. small air fryer and twin hot plates). Excellent shower."
United States
Anonymous traveler
The price is AED 688
AED 688 total
includes taxes & fees
11 Oct - 12 Oct
Stone's Throw - a holiday let that sleeps 2 guests in 1 bedroom
A small, single-story wooden cabin with a deck, surrounded by green grass and trees.

15. 1 bedroom accommodation in Herstmonceux, Hailsham

1 bedroom accommodation in Herstmonceux, Hailsham
Herstmonceux, Hailsham
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful little hut perfect for a relaxing stay,very friendly and helpful owners and ground keepers.Lots to do in area and very close to the beach and shops."
United States
PERRY CAMPBELL
The price is AED 1,131
AED 1,131 total
includes taxes & fees
3 Nov - 4 Nov
1 bedroom accommodation in Herstmonceux, Hailsham
A house with a glass door entrance, a small patio, and a garden with flowers.

16. 2 bedroom accommodation in Dungeness

2 bedroom accommodation in Dungeness
Dungeness
9.8 out of 10, Exceptional, (14 reviews)
"We first visited Helvetia in 2018, Little has changed, other than improvements to the Sun Room. It's a nice place to stay for a short break away from it all."
United States
John Nicholson
The price is AED 3,069
AED 3,069 total
includes taxes & fees
21 Oct - 22 Oct
2 bedroom accommodation in Dungeness
A property with a wooden exterior, a visible staircase, and a well-maintained lawn.

17. 1 bedroom accommodation in Herstmonceux, near Hailsham

1 bedroom accommodation in Herstmonceux, near Hailsham
Herstmonceux, near Hailsham
8.8 out of 10, Excellent, (5 reviews)
"A really lovely, tranquil spot for a break."
United States
Rhiannon L
The price is AED 1,131
AED 1,131 total
includes taxes & fees
3 Nov - 4 Nov
1 bedroom accommodation in Herstmonceux, near Hailsham
A brick building with a tiled roof, a wooden fence, and a grassy area in front.

18. 1 bedroom accommodation in Battle

1 bedroom accommodation in Battle
Battle
9.6 out of 10, Exceptional, (18 reviews)
"THIS WAS OUR 4TH VISIT AND IDEAL FOR IDEAL FOR THE PEACE AND QUITE WE WERE LOOKING FOR. Review independently collected and verified by Reevoo"
United States
John
The price is AED 1,485
AED 1,485 total
includes taxes & fees
18 Oct - 19 Oct
1 bedroom accommodation in Battle
A small brick building with a dark wooden extension, large glass doors, and a patio area with outdoor furniture and potted plants.

19. 2 bedroom accommodation in Hooe, Battle

2 bedroom accommodation in Hooe, Battle
Hooe, Battle
9.8 out of 10, Exceptional, (15 reviews)
"If you want to get away from it all & enjoy the peace of the Sussex countryside the Cart Lodge is perfect. Great little cottage, which is well equipped & in a good location to explore East Sussex. The sheep in the field are great fun, demanding their biscuits as you sit & enjoy the sun. Thanks Nina for a great week"
United Kingdom
Lois H.
The price is AED 1,522
AED 1,522 total
includes taxes & fees
7 Nov - 8 Nov
2 bedroom accommodation in Hooe, Battle
A two-story wooden house with a front porch, a small garden, and a visible front door.

20. Henley Bridge Holiday Cottage

Henley Bridge Holiday Cottage
Ashburnham, near Battle
9.0 out of 10, Wonderful, (7 reviews)
"Great place to stay really cozy with everything you need and more.Great outdoor space too.It was in an ideal location as we were walking the 1066 Country Walk"
United Kingdom
joy G.
The price is AED 1,906
AED 1,906 total
includes taxes & fees
27 Oct - 28 Oct
Henley Bridge Holiday Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchelsea Hotel Reviews

The Burlington Hotel

The Burlington Hotel

8/10 Good
"Evening meals could do with sprucing up a bit."
John 4-night trip
Posted 7 hours ago
The Burlington Hotel

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