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- House for 7 in Rye
- Handsome Coach House for 8 in Sedlescombe
- Hyrst Rise
- Spacious House for 7 in Saltdean
- Large Farmhouse for 12 in Magham Down
- Beachfront House for 8 in Middleton-on-Sea
- Number 5
- Spacious Three-Storey House for 8 in Camber
- 16th-Century Grade II-Listed Farmhouse for 8 in Heathfield
- 44 West Front Road
Group Cottages in Winchelsea
Rated Top 5 Most Popular Places in Sussex 2026 by our visitors
Large group cottages in and around Winchelsea, from converted barns to country houses that sleep 8 or more. Compare sleeping space, bedrooms and features such as hot tubs, games rooms and pet-friendly options, then check live availability with the booking partner.
1 cottage in Winchelsea39 more within 15 miles
Visitor Rating
4
Grade II-Listed Georgian Vicarage for 12 in Icklesham
Hot Tub
Sleeps 12
Pets 2
Bedrooms: 6
- 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
From £2,298 for 7 Nts
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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
From £958 for 7 Nts
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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
From £3,128 for 7 Nts
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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
From £973 for 7 Nts
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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
From £1,137 for 7 Nts
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Visitor Rating
4.5
Grade II-Listed Farmhouse for 8 in Icklesham
2 miles from Winchelsea
Hot Tub
Sleeps 8
Pets 3
Bedrooms: 4
- Hot tub in three gardens
- Grade II listed farmhouse
- Sleeps up to 12 guests
- Dining table seats 12
- Working Aga and inglenook fires
From £1,592 for 7 Nts
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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
From £1,512 for 7 Nts
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Visitor Rating
4.7
- Sleeps up to 20 guests
- Multiple self-contained lodges on site
- Minutes from medieval Rye town
- Camber Sands beach 4 miles away
- Easy access to Bodiam Castle
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- Private hot tub for groups
- Medieval Rye town on doorstep
- Camber Sands beach 3 miles away
- Bodiam Castle 20 minutes drive
- Spacious group social areas
From £2,193 for 7 Nts
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Visitor Rating
4
Spacious Three-Storey House for 8 in Camber
4 miles from Winchelsea
Hot Tub
Sleeps 8
Pets 2
Bedrooms: 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
From £957 for 7 Nts
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Visitor Rating
4.7
- Luxury detached East Sussex barn
- Exposed oak beams throughout
- Minutes from Hastings and Rye
- Private and peaceful countryside setting
- Ideal group touring base
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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
From £1,022 for 7 Nts
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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
From £2,310 for 7 Nts
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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
From £1,182 for 7 Nts
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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
From £1,052 for 7 Nts
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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
From £1,736 for 7 Nts
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Visitor Rating
4.1
- 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
Georgian Seafront House for 11 in St Leonards on Sea
8 miles from Winchelsea
Hot Tub
Sleeps 11
Pets 2
Bedrooms: 7
- Sleeps 11 in seven bedrooms
- Directly opposite Hastings Pier
- Spectacular sea views multiple floors
- Large open-plan living space
- Beach access across the road
From £1,696 for 7 Nts
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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
From £1,599 for 7 Nts
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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
From £863 for 3 Nts
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Zanzibar Beach House
East Sussex » St Leonards-On-Sea
8 miles from Winchelsea
Hot Tub
Sleeps 16
Pets 1
Bedrooms: 8
- 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
Large Enclosed Garden Cottage for 8 in Sedlescombe
8 miles from Winchelsea
Hot Tub
Sleeps 8
Bedrooms: 4
- 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
From £2,238 for 7 Nts
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Visitor Rating
4.6
- Sleeps 11 in five bedrooms
- Dedicated basement cinema room
- Three full bathrooms throughout
- Under 100 metres from beach
- Period townhouse with modern comforts
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Visitor Rating
4.9
Archery Retreat
East Sussex » St Leonards-On-Sea
8 miles from Winchelsea
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 5
- 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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More group cottages in Sussex
Popular towns and villages in and around Winchelsea