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- Eagles Nest at Greyfriars
- Lake View Millhayes
- The Old Doctors Manor House
- Shepps Cott
- Coast Guard House
- The Hideout
- The Boathouse
- Riverview
- Churchlands
- The Warren
- Vineyard View
- Little Ponds
- Stelling Minnis at Toms Cabin
- The Bolthole
- Luffs Farm
- Waterside Lodge
- Deerson Barn in Preston
- The Griffins Retreat
- Ramsgate at St Mildred’s Church
- Westwood Coach House
- Retreat at Reeves Estate
- Yew Tree Cottage
- Glebe Cottage
- Dairy Cottage
- The Beach Bungalow
- Amberlea
- Coastal at Total Retreat
- The Snug at Pickelden Farmhouse
- The Stables at Churchlands Farm
- Cliffhanger
Winchelsea Holiday Cottages
Rated Top 5 Most Popular Places in Kent 2026 by our visitors
Our Winchelsea holiday cottages offer you a perfect base in this historic hilltop town overlooking the Bexhill marshes. This ancient Cinque Port boasts medieval gates including the Strand Gate and New Gate alongside the atmospheric ruins of St Thomas' Church. You'll discover centuries of Sussex heritage within these atmospheric cobbled streets!
Whether you're travelling as families, couples or groups, our cottages provide comfortable stays with options from traditional rentals to glamping and lodge accommodation. Many properties feature hot tubs for ultimate relaxation after exploring nearby Rye, Camber Sands beach and the Romney Marsh. The UK's southeast coast awaits your discovery from this remarkable medieval settlement.
Visitor Rating
5
- Grade II listed historic apartment
- Private wood-fired hot tub for four
- Luxury bedrooms with premium bedding
- One mile from Winchelsea beach
- Secure garden perfect for dogs
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Visitor Rating
5
- Private wood-fired hot tub
- Grade II listed historic building
- Luxury mattresses and linens
- One mile from beach
- Pet-friendly with washing facilities
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Visitor Rating
4.9
- Hot tub on terrace
- Sleeps 8 luxury accommodation
- Canadian red cedar eco-build
- Rural views Brede Levels
- 2 miles from beaches
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Visitor Rating
4.9
- Hot tub with countryside views
- Fully enclosed dog-safe garden
- Luxury modern interiors
- Close to Rye and beaches
- Generous welcome pack included
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Visitor Rating
4.9
- Private hot tub
- Dog-secure garden
- Near historic Rye
- Close to Camber Sands
- Thoughtful welcome gifts
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Visitor Rating
4.5
- Hot tub on working vineyard
- Pet-friendly barn conversion sleeps 4
- Wood burner and underfloor heating
- Footpath access from the door
- Near Rye and Camber Sands
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Visitor Rating
5
- Private hot tub available
- Wood burner with free logs
- Five acres peaceful farmland
- Adults only romantic retreat
- Historic Rye four miles away
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- Beachfront location with sea views
- Eight en-suite bedrooms
- Hot tub on terrace
- Bar with coastal outlook
- Dog-friendly accommodation
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Visitor Rating
4.8
- Sea views from private roof terrace
- Luxury hot tub experience
- High-end interior finishes
- 5 minutes to beach
- Spacious rooms for large groups
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Visitor Rating
5
- Historic 350-year-old thatched cottage
- Private 6-seater hot tub
- Large enclosed lawned garden
- Pet-friendly countryside location
- Modern kitchen with Sky Movies
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- Private hot tub for four
- Ancient woodland setting location
- Adults only romantic retreat
- Historic Battle Abbey nearby
- Complete privacy and seclusion
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- Hot tub under trees
- Converted shipping container lodge
- Complete woodland privacy
- Adults only couples retreat
- Historic Battle location
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Visitor Rating
4.8
- Vineyard views from your doorstep
- Private wood-fired hot tub
- Complimentary wine tasting included
- Peaceful countryside location
- Cosy mezzanine king-size bedroom
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- Six en-suite ground-floor bedrooms
- Hot tub with vineyard views
- Games room with four activities
- 80 acres of vineyard walks
- Electric vehicle charging available
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Visitor Rating
4.8
- Private hot tub on decking
- Floor-to-ceiling countryside views
- Enclosed garden for dogs
- Contemporary wet room with underfloor heating
- Secluded Kent Weald location
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Visitor Rating
4.9
- Six-person hot tub with canopy
- Two king-size en-suite bedrooms
- Working farm with wildlife cameras
- Welcomes two dogs with facilities
- Near Sissinghurst Castle Gardens
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Visitor Rating
4.5
- Private hot tub with vineyard views
- Tennis court access
- Quirky hand-built lodge
- Two king-size en-suite bedrooms
- Close to Bodiam Castle
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Visitor Rating
4.7
- Private hot tub with vineyard views
- All on one level
- Enclosed dog-friendly garden
- Near historic Rye and beaches
- Peaceful countryside location
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Visitor Rating
4.9
- Hot tub with weatherproof canopy
- Dog walking fields on doorstep
- Four spacious bedrooms
- Fully enclosed garden
- Wood burner for cosy evenings
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Visitor Rating
5
- Private hot tub for six
- Large enclosed garden space
- Working farm peaceful setting
- Three comfortable bedrooms available
- Modern kitchen fully equipped
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Visitor Rating
4.8
- Stunning vineyard views
- Private hot tubs
- Three separate eco-cottages
- Perfect for large gatherings
- High-quality modern interiors
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Visitor Rating
4.9
- Outdoor heated pool
- Hot tub for year-round relaxation
- Games room with pool table
- Five spacious bedrooms
- Beautiful Kent countryside location
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Visitor Rating
5
- Private hot tub with rural views
- King-size beds with quality linen
- Dog-friendly with secure garden
- Modern tech in countryside setting
- Excellent local pubs nearby
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Visitor Rating
4.1
- Spacious farmhouse with countryside views
- Working farm with horses
- Four bathrooms - no morning queues
- Multiple reception rooms for large groups
- Close to vineyards and historical sites
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Visitor Rating
4.7
- Beautiful tiered garden
- Hot tub and sauna
- Exceptionally well-equipped kitchen
- Games room for all ages
- Peaceful Sussex countryside location
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Visitor Rating
4.7
- Huge single-storey property
- Four en-suite bedrooms
- Six-person hot tub
- Games table and Smart TVs
- Acre of enclosed garden
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Visitor Rating
4.9
- Hot tub with vineyard views
- Stunning barn conversion
- Open-plan luxury living space
- Near beaches and historic towns
- Perfect for family gatherings
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Visitor Rating
4.9
- Private hot tub
- One mile from beach
- Three comfortable bedrooms
- Dog-friendly accommodation
- Close to shops and pubs
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Visitor Rating
4.6
- Lakeside vineyard setting
- Private hot tub
- Stylish Scandinavian design
- Close to Bodiam Castle
- Cosy wood burner
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- Private hot tub for couples
- Stylish log cabin accommodation
- 13 acres of private grounds
- Air conditioning and gas heating
- Private parking for two cars
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Explore more of Kent
Popular towns and villages in and around Winchelsea
Ashford Bexley Birchington Brenchley Broadstairs Chatham Chilham Deal Ditton Dover Dunkirk Dymchurch Faversham Folkestone Goudhurst Herne Bay Hythe Ightham Kingsdown Lamberhurst Maidstone Margate New Romney Pluckley Ramsgate Rochester Romney Marsh Sandgate Sandwich Sevenoaks Staplehurst Stoke Sundridge Tenterden Tonbridge Tunbridge Wells Whitstable