Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- Castlemans Coach House
- Sea Dreams
- Marsh Mellow Camber Sands
- 4 West Street
- Denswood House
- Breeze
- 50 Harbour Road
- Hyrst Rise
- 44 West Front Road
- House On The Hill Hastings
- The Granary Ticehurst
- Wave Crest
- The Gate House Hadlow Down
- Hastings House
- Hastings Heights
- St Giles In The Wood
- The Old Vicarage Icklesham
- Knoll House
- Luffs Farm
- Waters Edge Pevensey Bay
- Ashdown Forest Escape
- Camberfornia
- Orchard House
- Archery Retreat
- Scrag Oak
- Cliffhanger
- Pett Level Beach House
- Primrose Place
- Casasands
- La Villa
Winchelsea Holiday Cottages
Our curated collection of Winchelsea cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Winchelsea holiday home today.
Visitor Rating
4
- Sleeps 12 in six bedrooms
- Games room with pool table
- Large enclosed garden with summer house
- Four bathrooms across three floors
- Walking distance to traditional pub
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Visitor Rating
4
- Sleeps 7 in 4 bedrooms
- Stunning Tillingham Valley views
- 10-minute walk to Rye centre
- Enclosed garden with BBQ
- Private parking for two cars
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Visitor Rating
5
- Sleeps 12 with five bathrooms
- Five private parking spaces included
- Games room with shuffleboard entertainment
- Enclosed garden perfect for dogs
- Ten minute walk to Rye centre
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Visitor Rating
4.8
- Central Rye location near shops
- Four bedrooms sleeping six guests
- Cosy wood burner in lounge
- Period Georgian house with character
- Walking distance to train station
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Visitor Rating
4.6
- Central Rye location near station
- Sleeps six across four bedrooms
- Enclosed courtyard with garden furniture
- Modern kitchen with Rangemaster cooker
- Walk to shops pubs and restaurants
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Visitor Rating
4.5
- Hot tub in three gardens
- Grade II listed farmhouse
- Sleeps up to 12 guests
- Dining table seats 12
- Working Aga and inglenook fires
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- 150 metres from Pett Level Beach
- Sleeps 8 in 4 bedrooms
- Parking for 4 cars included
- Large wraparound garden with patio
- Ground floor bedroom and bathroom
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Visitor Rating
4.7
- Sleeps eight across five bedrooms
- Stunning countryside to sea views
- Extensive gardens with play equipment
- Walking distance to historic Rye
- Perfect for multi-generational groups
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Visitor Rating
4
- Sleeps 8 with parking for 2
- 10 minute walk to sandy beach
- Enclosed garden with BBQ area
- Four bedrooms across three floors
- Dog-friendly with welcome pack included
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- Half mile from Camber Sands beach
- Sleeps eight across four bedrooms
- Fully enclosed garden with BBQ
- Private parking for two cars
- Two pets welcome at property
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Visitor Rating
4.9
- Sleeps 8 in two properties
- Four en-suite bedrooms throughout
- Enclosed Mediterranean courtyard garden
- Working farm in High Weald
- Three miles from historic Rye
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Visitor Rating
5
- 100 metres from Camber Sands beach
- Sleeps 12 in six bedrooms
- Dedicated snug games room entertainment
- Enclosed garden with play equipment
- Two ground floor en-suite bedrooms
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- Sleeps 10 with hot tub
- Five bedrooms and three bathrooms
- Games room with pool table
- Enclosed gardens for privacy
- Near Camber Sands beach
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- Sleeps 10 in five bedrooms
- Games room for group entertainment
- Three bathrooms throughout property
- Near Camber Sands beach
- Close to historic Rye town
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Visitor Rating
4.9
- Sleeps 7 with parking for 4 cars
- Four-acre private mown paddock access
- Three bathrooms including two en-suites
- High Weald AONB countryside views
- Red Lion pub just 20 metres away
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- Sleeps 10 in five bedrooms
- Three bathrooms for larger groups
- Sea views and beach nearby
- Enclosed garden with patio furniture
- Victorian house in Hastings Old Town
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Visitor Rating
5
- Grade II-listed with sea views
- Sleeps 10 across five bedrooms
- Four bathrooms for larger groups
- Hastings Old Town location
- Dining table seats twelve guests
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Visitor Rating
4.2
- Indoor heated swimming pool
- Sleeps 13 across seven bedrooms
- Parking for 10 cars included
- Welcomes four dogs no charge
- Full acre of private grounds
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Visitor Rating
4
- Sleeps six in Old Town location
- Wood burner and Smart TVs throughout
- Half mile walk to beach
- Two dogs welcome at property
- Four bedrooms with two bathrooms
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Visitor Rating
4
- Sleeps 11 in seven bedrooms
- Directly opposite Hastings Pier
- Spectacular sea views multiple floors
- Large open-plan living space
- Beach access across the road
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Visitor Rating
4.8
- Sleeps 8 in 5 bedrooms
- Three bathrooms throughout
- Enclosed garden with BBQ
- Dog-friendly, welcomes 3 dogs
- Near Battle, Rye and Hastings
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- Sleeps 10 with hot tub
- Two fully equipped kitchens
- Four en-suite bedrooms available
- Peaceful working vineyard setting
- Near Bodiam Castle and Battle
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- Beachfront property sleeping 16 guests
- Eight en-suite bedrooms included
- Hot tub with stunning sea views
- Secure parking for two cars
- Former award-winning boutique hotel standard
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Visitor Rating
5
- Heated outdoor pool April-October
- Four en-suite king-size bedrooms
- Parking for five cars
- Five miles from beaches
- Air-conditioned conservatory with garden access
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Visitor Rating
4.9
- Sleeps 10 adults plus 2 children
- Grade II-listed Georgian seaside home
- Five bedrooms with luxurious bathrooms
- Sea views from dining area
- Just 0.3 miles from beach
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Visitor Rating
4.8
- Private roof terrace with hot tub
- Six en-suite bedrooms sleep 14
- Five minutes walk to beach
- Kitchen dining seats 14 guests
- Former hotel renovated to luxury standard
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Visitor Rating
4.6
- Sleeps 8 in 5 bedrooms
- 4 bathrooms with 3 en-suites
- Three reception rooms with open fires
- Acres of enclosed gardens
- Walking distance to Bodiam Castle
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- Wheelchair accessible with lift
- Games room with table tennis
- Sleeps 10 across five bedrooms
- Six car parking spaces
- Battle Abbey views from garden
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- Private outdoor swimming pool for groups
- Five bedrooms sleeping ten guests comfortably
- Pool table and table tennis entertainment
- Lakeside garden with multiple seating areas
- One mile from Battle Abbey history
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Visitor Rating
4.7
- Gothic Revival tower with countryside views
- Sleeps eight across four spacious bedrooms
- Open-plan lounge perfect for group gatherings
- Surrounded by Eatenden Wood and wildlife
- Three miles from Battle Abbey history
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