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

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Winchelsea bed & breakfast

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

1. The Ship Inn

The Ship Inn
4.0 star property
Rye
8.6 out of 10, Excellent, (364 reviews)
"Breakfasts very good"
United Kingdom
Roberta
The price is ￥10,134
￥12,161 total
includes taxes & fees
Nov 16 - Nov 17
The Ship Inn
A traditional brick building with a white facade, a small attached structure, and a paved area with benches.

2. The Hope Anchor

The Hope Anchor
3.0 star property
Rye
9.0 out of 10, Wonderful, (238 reviews)
"Lovely stay, helpful staff, great location."
United Kingdom
William
The price is ￥13,290
￥15,948 total
includes taxes & fees
Nov 25 - Nov 26
The Hope Anchor
A cozy living room with a fireplace, a sofa, a table, and a TV.

3. The Kings Head Rye

The Kings Head Rye
4.0 star property
Rye
8.8 out of 10, Excellent, (221 reviews)
"Hotel was nice and comfortable overall. Breakfast was great! Only hiccup was that hotel rebooked us in a different room than I had booked without telling us, new room didn't have bed set up that we wanted."
United States
Maia
The price is ￥25,176
￥30,212 total
includes taxes & fees
Oct 27 - Oct 28
The Kings Head Rye
A spacious restaurant with wooden tables and chairs, decorative wall panels, and a chandelier.

4. OYO Eagle House Hotel, St Leonards Hastings

OYO Eagle House Hotel, St Leonards Hastings
3.0 star property
St Leonards-On-Sea
7.8 out of 10, Good, (478 reviews)
"Clean and comfortable room for a short stay. Adequate breakfast. Good location in terms of walking down to the seafront. Would note for travellers with accessibility issues the hotel is at the top of a very steep road so may not be suitable for mobility aid users."
United Kingdom
Alyx
The price is ￥7,711
￥9,639 total
includes taxes & fees
Nov 8 - Nov 9
OYO Eagle House Hotel, St Leonards Hastings
A row of white buildings with numbered doors, a wooden deck, and a clear sky.

5. The Bull Inn Lodges

The Bull Inn Lodges
3.0 star property
Cranbrook
8.6 out of 10, Excellent, (77 reviews)
"Really enjoy our stay."
United Kingdom
Sarah
The price is ￥14,511
￥17,414 total
includes taxes & fees
Oct 26 - Oct 27
The Bull Inn Lodges
A brick building with a tiled roof, a gated entrance, and a paved courtyard.

6. Forest Edge Motel

Forest Edge Motel
3.0 star property
Wadhurst
9.2 out of 10, Wonderful, (83 reviews)
"Great location and access to the area"
United Kingdom
Bruce
The price is ￥20,980
￥25,176 total
includes taxes & fees
Oct 26 - Oct 27
Forest Edge Motel
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.

7. The Laindons

The Laindons
5.0 star property
Old Town Hastings
10.0 out of 10, Exceptional, (149 reviews)
"The hotel staff was very friendly and accommodating. It was a very relaxing, quiet stay after days of hectic sightseeing the coast. The beds were so wonderful! The breakfast was fresh with many options made to order. We had a lovely stay."
United States
Maria
The price is ￥35,285
￥42,342 total
includes taxes & fees
Oct 26 - Oct 27
The Laindons
A large brick building with a garden patio featuring outdoor furniture and umbrellas.

8. Sissinghurst Castle Farmhouse

Sissinghurst Castle Farmhouse
3.5 star property
Cranbrook
9.8 out of 10, Exceptional, (61 reviews)
"Fantastic place to stay next door to the Sissinghurst Castle Gardens. Friendly and beautiful. We will definitely return"
United States
Katherina
The price is ￥42,363
￥50,836 total
includes taxes & fees
Oct 26 - Oct 27
Sissinghurst Castle Farmhouse
A building with a sign that reads "Eastbourne."

9. Eastbourne Reymar - B&B

Eastbourne Reymar - B&B
3.0 star property
Eastbourne
9.0 out of 10, Wonderful, (270 reviews)
"Fantastic stay, Nick was a very attentive and helpful host."
United Kingdom
Olivia
The price is ￥8,287
￥9,944 total
includes taxes & fees
Nov 1 - Nov 2
Eastbourne Reymar - B&B
A room with a bed, a dining table with various items, and a view of a garden through open doors.

10. Wilderness B&B

Wilderness B&B
4.0 star property
Ashford
9.2 out of 10, Wonderful, (54 reviews)
"Nice and private"
United Kingdom
Karen
The price is ￥19,056
￥19,056 total
includes taxes & fees
Oct 27 - Oct 28
Wilderness B&B
Front of property

11. Anne's House

Anne's House
5.0 star property
Hastings
10.0 out of 10, Exceptional, (33 reviews)
"Lovely room, very clean, delightful hosts, great breakfast-I would stay again!!!!"
United Kingdom
Christine
The price is ￥39,464
￥39,464 total
includes taxes & fees
Oct 27 - Oct 28
Anne's House
A coastal cityscape viewed from a high vantage point, including buildings, a sea view, and a clear sky.

12. The Highlands Inn

The Highlands Inn
3.0 star property
St Leonards-On-Sea
7.0 out of 10, Good, (314 reviews)
"Good location and reasonable rooms. Parking limited, although streets nearby. Slightly tired in places, however clean."
United Kingdom
Mark
The price is ￥8,917
￥10,701 total
includes taxes & fees
Oct 26 - Oct 27
The Highlands Inn
A restaurant with wooden tables and chairs, hanging pendant lights, a fireplace, and a bar area with shelves of bottles.

13. Ravilious

Ravilious
4.0 star property
Eastbourne
10.0 out of 10, Exceptional, (349 reviews)
"A beautiful property and wonderful hosts. Parking was easy, room was lovely and breakfast was delicious!"
Australia
Kellie
The price is ￥17,938
￥21,525 total
includes taxes & fees
Oct 26 - Oct 27
Ravilious
A balcony with a view of a road, a street lamp, and a small table with chairs.

14. The New England

The New England
4.0 star property
Eastbourne
9.8 out of 10, Exceptional, (134 reviews)
"Very friendly staff and nice breakfast, highly recommended"
United Kingdom
Lukas
The price is ￥22,728
￥27,274 total
includes taxes & fees
Oct 26 - Oct 27
The New England
A sunlit room with large windows, a wooden table, chairs, and a view of the sea and parked cars.

15. Beach Front Guest House

Beach Front Guest House
3.0 star property
Eastbourne
9.8 out of 10, Exceptional, (246 reviews)
"The owners and staff here are excellent, from very useful messaging before you arrive and through to the end of your stay"
United Kingdom
Jenny
The price is ￥17,151
￥20,581 total
includes taxes & fees
Nov 8 - Nov 9
Beach Front Guest House
A spacious lounge area with multiple seating options, including sofas and chairs, and a dining area with tables and chairs.

16. Moore House

Moore House
3.5 star property
Old Town Hastings
9.8 out of 10, Exceptional, (168 reviews)
"Amazing location, clean room and very kind staff!!"
United Kingdom
Patricia
The price is ￥25,351
￥30,421 total
includes taxes & fees
Oct 26 - Oct 27
Moore House
An outdoor patio area with multiple tables and chairs, brick walls, and large windows.

17. The Ship Hotel

The Ship Hotel
3.0 star property
New Romney
8.2 out of 10, Very good, (452 reviews)
"Great staff that could not do enough for us, newly decorated room very good restaurant (but very busy) breakfast is amazing but it you do have to be a bit patient but it is very much worth the wait. Parking is adequate but i would think if you turn up later in the evening you would struggle for space Our second stay there and would do it again"
United Kingdom
Paul
The price is ￥17,257
￥20,709 total
includes taxes & fees
Nov 7 - Nov 8
The Ship Hotel
A garden pathway with a glass structure in the center, surrounded by lush greenery and climbing plants.

18. St Benedict B&B

St Benedict B&B
2.0 star property
St Leonards-On-Sea
9.6 out of 10, Exceptional, (81 reviews)
"This property is unbelievably beautiful and comfortable. Easy on street parking and close to the sea front and good restaurants. The hosts were welcoming and helpful. We highly recommend staying and experiencing Victorian living at its best."
United States
John
The price is ￥24,477
￥29,372 total
includes taxes & fees
Oct 28 - Oct 29
St Benedict B&B
A bedroom with a large window overlooking a beach, a bed with white and brown bedding, and a lamp on a bedside table.

19. Alexander's

Alexander's
4.0 star property
Hastings
8.2 out of 10, Very good, (347 reviews)
"I spent two nights here while attending a local event. Very kind hosts and a well-equipped room in a great location (my event was only a short walk away). I had a nice stay here."
United States
James
The price is ￥18,358
￥22,030 total
includes taxes & fees
Oct 26 - Oct 27
Alexander's
A hotel room with a large bed, a nightstand with a lamp, a bathroom visible through an open door, and a small table with a chair.

20. The Wayfarer

The Wayfarer
3.5 star property
Bexhill-on-Sea
9.6 out of 10, Exceptional, (250 reviews)
"A really lovely hotel with even lovelier staff. Right next to the beach and perfect for our little get away. Breakfast was also really lovely and the staff were really accommodating"
United Kingdom
Megan
The price is ￥23,603
￥28,324 total
includes taxes & fees
Oct 27 - Oct 28
The Wayfarer
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

Cavendish Hotel

Cavendish Hotel

10/10 Excellent
"Good hotel"
Justin 2-night trip
Posted 1 hour ago
Cavendish Hotel

Find out more about Winchelsea

Winchelsea B&B information

Number of reviews
2,993
Accommodation
47 B&B
Lowest Price
￥9,639
Highest Price
￥50,836

Frequently asked questions

Searching for B&Bs in Winchelsea?
If you're looking for something a little quirkier than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. During your time in Winchelsea, you might want to spend some time strolling along the water at Winchelsea Beach and Pett Level Beach.
Why choose a B&B versus a traditional hotel?
With attentive service, opportunities to mingle with other guests, and breakfast served on site, B&Bs provide a one-of-a-kind environment.
What are the best B&Bs in Winchelsea?
Below are some B&Bs in the surrounding area: The Hope Anchor: 13 rooms. 2 mi (3.2 km) from the heart of Winchelsea. Enjoy the free cooked breakfast and patio area. The Ship Inn: 11 rooms. 1.9 mi (3.1 km) from the downtown core. Enjoy the unique décor and onsite dining. OYO Eagle House Hotel, St Leonards Hastings: 21 rooms. Situated 8.2 mi (13.2 km) from the heart of Winchelsea. Enjoy the free English breakfast and bar/lounge. The Highlands Inn: 12 rooms. 8.6 mi (13.9 km) from the heart of downtown.
What's the best time of year to stay at a B&B in Winchelsea?
When you're dreaming of a getaway to Winchelsea, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 61°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Winchelsea is 29 inches.
What is there to do in Winchelsea?
Spend some time exploring Winchelsea Beach and High Weald if you're hoping to see some of the area's natural features. You might put Pett Level Beach and St. Thomas the Martyr on your list if you want to see more of the area.
How can I get to and around Winchelsea?
Planning your excursions in and around Winchelsea is easier with these transportation options. Fly into Gatwick Airport (LGW), which is located 41.2 mi (66.3 km) away from the heart of the city. If you'd like to venture out around the area, you may want a rental car for your journey.

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