Plan your trip

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

Photo by Adam Kumiszcza (Creative Commons Attribution-Share Alike 4.0)

Find a Bed and Breakfast in Winchelsea from CA $69

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Sign in

  • Be picky

    Search almost a million properties worldwide

    • Check prices for these dates

    Check prices for these dates, December 14–15, 2026

    View in a map

    Our top choices for Winchelsea bed & breakfast

    1. The Ship Inn

    A neatly made bed with a lamp, a bottle, and glasses on a bedside table, and a letter 'N' on the wall.

    2. The Hope Anchor

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

    3. The Kings Head Rye

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

    4. NORTHRISE RETREAT

    A large house with a hot tub in the foreground, a deck, and a well-maintained lawn.

    5. OYO Eagle House Hotel, St Leonards Hastings

    A spacious dining area with wooden tables and chairs, a chandelier, and decorative wall panels.

    6. Eastbourne Reymar - B&B

    A room with a blue carpet, two armchairs, a sofa, and a coffee table.

    7. The Laindons

    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.

    8. 17 Wilmington Square

    A hotel room with two beds, each with a headboard, and two wall-mounted lamps.

    9. Forest Edge Motel

    A row of wooden cabins with red roofs, surrounded by a wooden fence, set against a backdrop of green fields and trees.

    10. Sissinghurst Castle Farmhouse

    A rural landscape with a large open field, dense greenery, and a few scattered structures.

    11. Anne's House

    Garden

    12. Beach Front Guest House

    A wooden door with a number 7, leading to a bedroom with a bed, pillows, and a nightstand.

    13. Alexander's

    A bedroom with a large window overlooking a beach, a bed with white and brown bedding, and a lamp on a bedside table.

    14. Ravilious

    A pier extending into the sea with a building at its end.

    15. The New England

    A balcony with a view of a road, a street lamp, and a small table with chairs.

    16. The Highlands Inn

    A coastal cityscape viewed from a high vantage point, including buildings, a sea view, and a clear sky.

    17. Moore House

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

    18. St Benedict B&B

    A garden pathway with a glass structure in the center, surrounded by lush greenery and climbing plants.

    19. The Ship Hotel

    A dining area with brick walls, exposed beams, and a fireplace. There are several tables and chairs arranged for dining.

    20. Wilderness B&B

    A black wooden house with a sloped roof, a wooden door, and a window.

    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.

    View all properties

    Learn more about Winchelsea

    This medieval town's cobblestone streets lead to the ancient Court Hall museum and St Thomas' Church with its panoramic views. Climb Strand Hill for sweeping vistas of Romney Marsh or join locals at The New Inn for traditional English pub fare.

    See all hotels in Winchelsea

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

    Photo by Adam Kumiszcza

    Top reviews in Winchelsea

    The Hope Anchor

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

    The Ship Inn

    A neatly made bed with a lamp, a bottle, and glasses on a bedside table, and a letter 'N' on the wall.

    Moore House

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

    The Laindons

    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.

    Ravilious

    A pier extending into the sea with a building at its end.

    Sissinghurst Castle Farmhouse

    A rural landscape with a large open field, dense greenery, and a few scattered structures.

    The Wayfarer

    A hotel room with a bed, a desk, a chair, and a lamp.

    Beach Front Guest House

    A wooden door with a number 7, leading to a bedroom with a bed, pillows, and a nightstand.

    Eastbourne Reymar - B&B

    A room with a blue carpet, two armchairs, a sofa, and a coffee table.

    The Rose & Crown

    A traditional brick building with a sign reading "ROSE AND CROWN."

    The New England

    A balcony with a view of a road, a street lamp, and a small table with chairs.

    OYO Eagle House Hotel, St Leonards Hastings

    A spacious dining area with wooden tables and chairs, a chandelier, and decorative wall panels.

    Alexander's

    A bedroom with a large window overlooking a beach, a bed with white and brown bedding, and a lamp on a bedside table.

    The Sheldon B&B

    A bedroom with a large bed, a wooden wardrobe, a desk with a chair, a vanity with a mirror, and a window with a view of buildings.

    Frequently Asked Questions

    What is the nightly rate for a Bed and Breakfast in Winchelsea?

    Prices for B&Bs in Winchelsea often vary, but you can find a great deal from CA $69 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchelsea B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

    When is the best time to book a Bed & Breakfast in Winchelsea?

    The best time to book a B&B in Winchelsea is during the late spring and early summer months, particularly May and June. This period is particularly inviting as the weather is typically mild, with temperatures ranging from around 12 to 20 degrees Celsius. The charming coastal town comes alive with vibrant flowers and bustling local markets, making it an ideal time for leisurely strolls along the picturesque streets.

    As the summer approaches, the peak tourist season kicks off in July and August. This is when visitors flock to Winchelsea for its beautiful beaches, historical sites, and outdoor activities. The lively atmosphere during these months is superb for families and groups looking to soak up the sun while enjoying local events and festivals. Expect to find an array of activities, from beachcombing to exploring the nearby Rye Harbour Nature Reserve.

    If you're seeking a more budget-friendly experience, consider visiting in September. The weather remains pleasant, and the summer crowds start to dwindle, allowing for a more relaxed exploration of the area's attractions. This quieter month is superb for those who appreciate the tranquillity of coastal walks and the beauty of the changing scenery.

    What is the difference between a Winchelsea Bed & Breakfast and a hotel?

    Every Winchelsea B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchelsea B&Bs.

    Explore a world of travel with Expedia