Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- Chestnut Cottage at The Cottages
- Overchurch
- Sunset Lodge
- Paisley Cottage
- Westpoundland View
- Lake View Millhayes
- The Griffins Retreat
- Coast Guard House
- Amazing Cottage
- Dreamwood Lodge
- Luffs Farm
- Solton Manor
- Gem Manor
- Sunset View Millhayes
- Amberlea
- Bokes Barn
- Maple Cottage
- Sunset Retreat
- Birch Cottage
- Moon Cottage
- Vineyard Hollow
- Churchlands Barn
- Riverview
- Stone Cottage Kingsnorth
- Churchlands
- Great Everden Manor Estate
- The Hideout
- The Grape Escape
- Waterside Lodge
- The Old Cowshed
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
4.9
- Hot tub with countryside views
- Fully enclosed dog-safe garden
- Luxury modern interiors
- Close to Rye and beaches
- Generous welcome pack included
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Private hot tub
- Dog-secure garden
- Near historic Rye
- Close to Camber Sands
- Thoughtful welcome gifts
View Cottage
[+] To Favourites
- Beachfront location with sea views
- Eight en-suite bedrooms
- Hot tub on terrace
- Bar with coastal outlook
- Dog-friendly accommodation
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
- 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
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Stunning vineyard views
- Private hot tubs
- Three separate eco-cottages
- Perfect for large gatherings
- High-quality modern interiors
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Beautiful tiered garden
- Hot tub and sauna
- Exceptionally well-equipped kitchen
- Games room for all ages
- Peaceful Sussex countryside location
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
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
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Private hot tub
- One mile from beach
- Three comfortable bedrooms
- Dog-friendly accommodation
- Close to shops and pubs
View Cottage
[+] To Favourites
Visitor Rating
4.6
- Lakeside vineyard setting
- Private hot tub
- Stylish Scandinavian design
- Close to Bodiam Castle
- Cosy wood burner
View Cottage
[+] To Favourites
Visitor Rating
4.8
- Cosy one-bedroom lodge
- Enclosed private garden with hammock
- Rainfall shower with luxury toiletries
- Dog-friendly with secure outdoor space
- Cafe and shop next door
View Cottage
[+] To Favourites
Visitor Rating
5
- Private hot tub for six
- Homemade scones on arrival
- Games room with multiple activities
- Flexible bedroom arrangements
- Enclosed garden for pets
View Cottage
[+] To Favourites
Visitor Rating
5
- Wood-fired hot tub relaxation
- Ground floor accessible accommodation
- Electric vehicle charging point
- Enclosed gardens with fire pit
- Modern kitchen with wine cooler
View Cottage
[+] To Favourites
Visitor Rating
5
- Newly renovated stylish property
- Wood-fired hot tub
- Three spacious bedrooms
- Garden with BBQ
- Near historic Kent attractions
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Hot tub with countryside views
- Stunning oak beams and vaulted ceiling
- Near historic Rye and Camber Sands
- Cosy wood burner for winter evenings
- Fully equipped modern kitchen
View Cottage
[+] To Favourites
- Sleeps 24 in nine bedrooms
- Indoor pool and hot tub
- Marquee seats 90 guests
- Tennis court and gym facilities
- 40-space car park included
View Cottage
[+] To Favourites
- Indoor pool and hot tub
- Sleeps 48 across seven properties
- 12th-century estate with 7 acres
- Floodlit tennis court and gym
- Marquee for 90 guests available
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Wood-fired hot tub under stars
- Peaceful countryside location
- Close to Canterbury
- Spotlessly clean accommodation
- Train station walking distance
View Cottage
[+] To Favourites
- Sleeps 14 with hot tub
- Six bedrooms and six bathrooms
- Tennis court and play area
- 1.5 acres of private grounds
- Six car parking spaces
View Cottage
[+] To Favourites
Visitor Rating
4.7
- Two hot tubs with vineyard views
- Luxury barn conversion in Kent
- Sleeps 12 across 6 bedrooms
- Perfect for group celebrations
- Close to beaches and attractions
View Cottage
[+] To Favourites
- Authentic Japanese tea house retreat
- Private hot tub in separate building
- Traditional tatami mats and futon bedding
- Peaceful Zen garden with maples
- Near Leeds Castle and Canterbury
View Cottage
[+] To Favourites
Visitor Rating
4.9
- Private hot tub
- Peaceful village location
- Near historic Rye
- Garden for outdoor dining
- Close to vineyards
View Cottage
[+] To Favourites
- Private hot tub with river views
- Three bedrooms sleeping five guests
- Two miles from Canterbury Cathedral
- Raised terrace and courtyard garden
- Modern kitchen with full appliances
View Cottage
[+] To Favourites
Visitor Rating
4.4
- Vineyard setting with amazing views
- Private hot tub on terrace
- Stylish brick lookers hut
- Wood burner for cosy evenings
- Close to Rye and beaches
View Cottage
[+] To Favourites
Explore more of Kent
Popular towns and villages in and around Winchelsea
Ashford Bexley Birchington Blackheath 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 Stone Sundridge Tenterden Tonbridge Tunbridge Wells Whitstable