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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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 £343
includes taxes & fees
25 Sept - 26 Sept
1 bedroom accommodation in Winchelsea Beach, near Rye
A traditional building with a sign for 'Swan Cottage Tea Rooms' and 'Accommodations' offering real ales and good food.

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 £233
includes taxes & fees
6 Sept - 7 Sept
An unusual two-storey apartment with beams and an open fire.
A white brick building with a black door, multiple windows, and a visible sign on the right side.

3. 3 Cinque Ports Street

3 Cinque Ports Street
2.0 star property
Rye
The price is £427
includes taxes & fees
31 Aug - 1 Sept
3 Cinque Ports Street
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
9.6 out of 10, Exceptional, (5 reviews)
"Very comfortable accommodation and so central to shops and restaurants. Particularly loved the wood burning stove."
United States
Sheila Davies
The price is £233
includes taxes & fees
20 Sept - 21 Sept
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 £210
includes taxes & fees
1 Sept - 2 Sept
The Grain Store - a holiday let that sleeps 2 guests in 1 bedroom

6. Pett Beach Cove - a holiday let that sleeps 2 guests in 1 bedroom

Pett Beach Cove - a holiday let that sleeps 2 guests in 1 bedroom
Hastings
The price is £640
includes taxes & fees
3 Sept - 4 Sept
Pett Beach Cove - 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.

7. 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 £507
includes taxes & fees
10 Sept - 11 Sept
4 bedroom accommodation in Pett
A cozy cottage with a sloped roof, a small porch, and a well-maintained garden.

8. 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)
"Had a great time, thank you very much ! Would definitely stay again! Good location, easy to get into Rye and surounds."
United States
Anonymous traveller
The price is £223
includes taxes & fees
1 Sept - 2 Sept
The Garden Room - a holiday let 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 £333
includes taxes & fees
22 Sept - 23 Sept
2 bedroom accommodation in Lydd, Romney Marsh
A wooden deck with a wooden chair and table, a blanket, and breakfast items.

10. 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
8.8 out of 10, Excellent, (5 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 £257
includes taxes & fees
1 Sept - 2 Sept
Ernest - a holiday let by Bloom Stays that sleeps 2 guests in 1 bedroom
A table with a bottle of wine, a glass of wine, and a vase with flowers.

11. 1 bedroom accommodation in Cowbeech, near Hailsham

1 bedroom accommodation in Cowbeech, near Hailsham
Cowbeech, near Hailsham
10.0 out of 10, Exceptional, (3 reviews)
"Excellent lodge. Everything you need for a lovely relaxing break. Beautiful view. Central to lots of places to visit. Hosts very friendly."
United States
Viv Emmens
The price is £143
includes taxes & fees
10 Sept - 11 Sept
1 bedroom accommodation in Cowbeech, near Hailsham
A cobblestone street lined with traditional buildings, some with ivy and flower boxes, and street lamps.

12. 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, (19 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 £838
includes taxes & fees
27 Sept - 28 Sept
Mafeking by inspirestays-com - a cottage that sleeps 6 guests in 3 bedrooms
A white building with multiple windows and doors, stone steps leading to a gated entrance, and potted plants on the walls.

13. 1A Coastguard Cottages

1A Coastguard Cottages
3.0 star property
Rye
The price is £502
includes taxes & fees
3 Sept - 4 Sept
1A Coastguard Cottages
A small brick building with a dark wooden extension, large glass doors, and a patio area with outdoor furniture and potted plants.

14. 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 £337
includes taxes & fees
24 Sept - 25 Sept
2 bedroom accommodation in Hooe, Battle
A house with a glass door entrance, a small patio, and a garden with flowers.

15. 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 £661
includes taxes & fees
25 Sept - 26 Sept
2 bedroom accommodation in Dungeness
A two-story wooden house with a front porch, a small garden, and a visible front door.

16. Henley Bridge Holiday Cottage

Henley Bridge Holiday Cottage
Ashburnham, near Battle
8.8 out of 10, Excellent, (6 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 £317
includes taxes & fees
24 Sept - 25 Sept
Henley Bridge Holiday Cottage

17. 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 £415
includes taxes & fees
11 Sept - 12 Sept
1 bedroom accommodation in Battle
A small blue house with a wooden deck, surrounded by a grassy yard and trees.

18. 1 bedroom accommodation in Herstmonceux, near Hailsham

1 bedroom accommodation in Herstmonceux, near Hailsham
Herstmonceux, near Hailsham
10.0 out of 10, Exceptional, (2 reviews)
"We had a ln absolutely lovely weekend away, so peaceful and the hut was very cosy and welcoming, would definitely return."
United States
Neil Brooks
The price is £237
includes taxes & fees
28 Sept - 29 Sept
1 bedroom accommodation in Herstmonceux, near Hailsham
A beachside building with outdoor seating and umbrellas.

19. 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, (2 reviews)
"Stone’s Throw was so close to the beach but also the Royal Military Canal and the High Street, so a perfect location. An amazing property, so small but with everything we could possibly need for a few days away. Beautifully designed with a stylish vibe. A tardis sprang to mind as we opened the door! Spotlessly clean and bright and welcoming. Everything had been thought about carefully, even storage, under the bed. Such a comfortable bed too. We were fully informed about everything and lots of...
United States
Carol W.
The price is £142
includes taxes & fees
1 Sept - 2 Sept
Stone's Throw - a holiday let that sleeps 2 guests in 1 bedroom
A small wooden cottage with a tiled roof, a gravel driveway, and a wooden fence.

20. 1 bedroom accommodation in Mersham, near Ashford

1 bedroom accommodation in Mersham, near Ashford
Mersham, near Ashford
10.0 out of 10, Exceptional, (1 review)
"Nice peaceful and relaxing 4 nights. Host's were friendly and helpful, accommodation clean and well appointed."
United States
Trevor Paveley
The price is £223
includes taxes & fees
25 Sept - 26 Sept
1 bedroom accommodation in Mersham, near Ashford
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 Grand Hotel Eastbourne

The Grand Hotel Eastbourne

8/10 Good
"Absolutely lovely stay ! Staff were pleasant !"
Hayley 1-night trip
Posted 13 hours ago
The Grand Hotel Eastbourne

Find out more about Winchelsea

Winchelsea Cottages information

Number of reviews
149
Accommodation
711 Cottages
Lowest Price
£142
Highest Price
£838

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