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Windchasers internal courtyard with dining area and hot tub

group stays

Gather your loved ones and choose from several options designed to accommodate larger groups. Cosy cottages offer a home-from-home that’s perfect for family groups, or holiday parks offer a wide range of facilities such as pools and playgrounds for keeping little ones entertained. Campsites are another great alternative with several scenic spots to enjoy the outdoors together, while sleek self-catering apartments or glamping sites offer a chic stay for groups of friends or celebrations. From countryside to coast, the Island offers some idyllic locations for R&R and making new memories together.

Save up to 10%
Windchasers internal courtyard with dining area and hot tub
By The Sea, Group Stays, Hot Tubs & Pools, IOW Apartments & Villas | Cowes

Windchasers

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Castle Road Apartment decking with outdoor furniture and a sea view
By The Sea, Group Stays, IOW Apartments & Villas | Cowes

Castle Road Apartment

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Sleeps up to 6 people
Adults Only
Adults only
Car Parking icon
Car parking
Save up to 10%
The Chambers Apartment lounge
Dog Friendly, Family Holidays, Group Stays, IOW Apartments & Villas | Cowes

The Chambers Apartment

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Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Theatre House a view of the street below looking towards the sea
By The Sea, Family Holidays, Group Stays, IOW Apartments & Villas | Cowes

Theatre House

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Sleeps up to 7 people
Children Welcome icon
Children welcome
Sea View icon
Sea view
Art Deco HouseUK exterior
Accessible Breaks, Group Stays, Luxury Stays, Unique & Glamping, IOW Unique Retreats | Shanklin

Art Deco HouseUK

Bed Icon
Sleeps up to 16 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
New Bay deck
By The Sea, Group Stays, Hot Tubs & Pools, IOW Cottages | St Lawrence

Bay View

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Car Parking icon
Car parking
Save up to 10%
Coach House spacious living area with large dining table
Family Holidays, Group Stays, IOW Cottages | Cowes

Coach House

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Close to Beach icon
Close to beach
Save up to 10%
The View Point roof terrace
By The Sea, Dog Friendly, Group Stays, IOW Cottages | Cowes

The View Point

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Three Gables front elevation
Countryside Getaways, Dog Friendly, Group Stays, IOW Cottages | Near Yarmouth

Three Gables

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Regatta Cottage treble bedroom with a double and single bed
Family Holidays, Group Stays, IOW Cottages | Cowes

Regatta Cottage

Bed Icon
Sleeps up to 7 people
Children Welcome icon
Children welcome
Close to town
Close to town
The Watch House roof terrace with sea views
By The Sea, Family Holidays, Group Stays, IOW Cottages | Cowes

The Watch House

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Sea View icon
Sea view
Bermuda House double bedroom
By The Sea, Family Holidays, Group Stays, IOW Cottages | Ventnor

Bermuda House

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Close to Beach icon
Close to beach
Seaview Holidays exterior view of properties
Dog Friendly, Family Holidays, Group Stays, IOW Cottages | Seaview

Seaview Holidays

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Westhill king-size bedroom
By The Sea, Dog Friendly, Group Stays, IOW Cottages | Cowes

Westhill

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Rotherwood lounge area
By The Sea, Dog Friendly, Group Stays, IOW Cottages | Cowes

Rotherwood

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Seacroft Cottage dining area with view to the garden
IOW Cottages, Dog Friendly, Family Holidays, Group Stays | Bembridge

Seacroft Cottage

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Firefly House double bedroom
Dog Friendly, Family Holidays, Group Stays, IOW Cottages | Cowes

Firefly House

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Dog Friendly icon
Dog friendly
Save up to 10%
Crews Nest twin bedroom
Family Holidays, Group Stays, IOW Cottages | Cowes

Crews Nest

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Close to town
Close to town
Save up to 10%
Crossjack Cottage dining table and kitchen
By The Sea, Family Holidays, Group Stays, IOW Cottages | Cowes

Crossjack Cottage

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Close to town
Close to town
Save up to 10%
Fellows House kitchen
Family Holidays, Group Stays, Luxury Stays, IOW Cottages | Cowes

Fellows House

Bed Icon
Sleeps up to 8 people
Children Welcome icon
Children welcome
Car Parking icon
Car parking
Save up to 10%
Beken House kitchen
By The Sea, Family Holidays, Group Stays, IOW Cottages | Cowes

Beken House

Bed Icon
Sleeps up to 10 people
Children Welcome icon
Children welcome
Bed Linen Included
Bed linen included
Save up to 10%
The Retreat kitchen and dining area
By The Sea, Family Holidays, Group Stays, IOW Cottages | Cowes

The Retreat

Bed Icon
Sleeps up to 7 people
Children Welcome icon
Children welcome
Car Parking icon
Car parking