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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

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

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    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.

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    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.

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