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Group friendly cottages and houses

Group breaks on the Isle of Wight offer a blend of natural beauty, historical charm, and adventure, making for an ideal destination for friends, families, or colleagues seeking a memorable getaway. And if you are looking for holiday rentals for large groups, there’s plenty of choice.

The National Trust's Mottistone Manor Farmhouse is a spacious holiday cottage set in the picture-perfect village of Mottistone, with far-reaching views over fields to the sea. It occupies an enviable location close to Mottistone Gardens and the local church. Sleeping fourteen guests, the Farmhouse is surrounded by large, secluded gardens making it perfect for family gatherings and outdoor games.

If you are looking for a secluded place to stay as a large group but with your own space, Newbarn Country Cottages in Gatcombe are four beautiful conversions in a secluded downland valley in the centre of the Island. Sleeping 16 across all properties, there’s even a hot tub to enjoy.

For large group celebrations, The Hermitage in Ventnor is an impressive country house situated in an elevated rural position in just over 11 acres of private grounds. There is a choice of 10 bedrooms all with either en suite shower or bathroom as well as a gym, games room and snug full of toys and games for younger members of the group.

Family-friendly comfortable cottages and a quirky shepherd’s hut are waiting to welcome you at Godshill Park Cottages and Hut. Set on a working livestock farm in a hamlet in part of the Isle of Wight National Landscape, it’s an ideal setting for stargazing, countryside walks and peace and tranquillity. The central location ensures that the many attractions across the Island are just a short journey away.

There’s plenty of space for a group rustic retreat at the renowned Garlic Farm with seven beautifully converted holiday cottages and five luxury yurts, sleeping between two and ten and up to 50 across all. Guests will have exclusive use of a tennis court, football pitch and games room, as well as making the most of the popular on-site restaurant serving up tasty local produce for breakfast, lunch and dinner.

Big enough to sleep the largest of families but equally cosy and welcoming, Tapnell Manor has the rustic appeal of an old farmhouse. Set between two farms, with views towards Tennyson Down and The Solent, you will find yourself surrounded by natural beauty.

Inside the house, there are plenty of rooms for guests to spread out: a games room for the more active, and plenty of open fires for the more relaxed. The farmhouse has 10 bedrooms and outside, there's room to roam, with ponds, ornaments and a wide assortment of flora and fauna to keep green fingers occupied.

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Number of results: 44

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Classic Cottages

Type

Type:

Self-Catering

ISLANDWIDE

For over 45 years, Classic Cottages have been the independent holiday cottage and glamping specialists. Still run and owned by the founding family, we pride ourselves on our local expertise in our areas.

Dates

From:

1 Jan 2025to31 Dec 2025
Island Holiday Homes

Type

Type:

Self-Catering

ISLANDWIDE

Island Holiday Homes is an established agency renowned for delivering top-quality self-catering and serviced accommodation across the Isle of Wight. With a rich history rooted in exceptional service and a commitment to quality, Island Holiday Homes…

Dates

From:

1 Jan 2025to31 Dec 2025
Tourism For All
The Bay Colwell Holiday Resort

Type

Type:

Self-Catering

COLWELL BAY

The Bay Colwell is situated on the beautiful west coast of the Isle of Wight and just a short stroll from the wonderful Colwell Bay beach.

Dates

From:

1 Feb 2025to31 Dec 2025

From:

1 Jan 2026to31 Jan 2026
Gradings
- 4 Visit England Stars Holiday Park
4 Visit England Stars Holiday Park
The Garlic Farm Cottages and Luxury Yurts

Type

Type:

Self-Catering

NEWCHURCH

Self-catering cottages and luxury yurts on the Garlic Farm. A unique and beautiful place to stay with unspoilt scenery, farm walks and the Garlic Farm shop and restaurant on site with discounts for their guests. Tennis court, football pitch, games…

Dates

From:

1 Jan 2025to31 Dec 2025
Tapnell Farm Holiday Destination

Type

Type:

Holiday Village

YARMOUTH

Tapnell Farm is a family owned, award-winning holiday destination set in the beautiful rural West Wight countryside, commanding the most amazing sea views and stunning sunsets!
Home to Tom’s Eco Lodge glamping and farm accommodation, Tapnell Farm…

Dates

From:

1 Jan 2025to31 Dec 2025
Three Gables

Type

Type:

Self-Catering

Newbridge

Three Gables holiday home is in the centre of the small rural village of Newbridge on the western side of the Island.

Dates

From:

1 Jan 2025to31 Dec 2025
Holiday Accommodation at Calbourne Water Mill

Type

Type:

Self-Catering

CALBOURNE

Amongst the 35 acre grounds of Calbourne Water Mill, one of the Island's main attractions, there are luxury eco lodges and traditional cottages.

Dates

From:

1 Jan 2025to31 Dec 2025
The Hermitage

Type

Type:

Self-Catering

VENTNOR

An impressive country house situated in an elevated rural position in just over 11 acres of private grounds. Perfect accommodation for large group celebrations.

Dates

From:

1 Jan 2025to31 Dec 2025
Beach Homes on Priory Bay

Type

Type:

Self-Catering

SEAVIEW

Uniquely, these two properties have direct access to Priory Bay via a private track with yummy orchard, Victorian folly and stunning woodland. Not many of you will have seen a taller or more beautiful Oak tree.

Dates
Kingston Manor

Type

Type:

Self-Catering

VENTNOR

Beautiful Grade 2* medieval manor house with lovely gardens, sleeps up to 16 in 8 bedrooms, very peaceful, beautiful surroundings, within reach of everything. Perfect for a large family & friends get-together.

Dates

From:

19 Mar 2025to1 Nov 2025
Brummell Barn

Type

Type:

Self-Catering

Shorwell, Newport

Spacious and well-equipped self-catering cottage on a beautiful Isle of Wight working farm. Indoor pool and games rooms available for use as well as a children's playground and surrounded by superb walking and cycling trails in an AONB.
Suited to…

Dates

From:

20 Dec 2024to3 Nov 2025
Just For You Holiday Homes

Type

Type:

Self-Catering

Just For You Holiday Homes provide a home away from home, personalised and unparalleled service, so you can enjoy an unforgettable holiday experience.

Dates

From:

1 Jan 2025to31 Dec 2025
Gradings
- Visitor Ready Accredited by VisitEngland
Visitor Ready Accredited by VisitEngland
Snaptrip

Type

Type:

Self-Catering

ISLANDWIDE

Home to the largest collection of self-catering accommodation on the Isle of Wight, Snaptrip is a trusted marketplace for holiday cottages online.

Dates

From:

1 Jan 2025to31 Dec 2025
Fair Isle Holiday Cottages

Type

Type:

Self-Catering

NEWPORT

Fair Isle Holiday Cottages is a family-run business offering 7 thoughtfully designed holiday homes, including 5 newly built stylish contemporary lodges and 2 cosy cottages, all with stunning countryside views.

Dates

From:

1 Jan 2025to31 Dec 2025
Spinnakers - Fort Victoria

Type

Type:

Self-Catering

Norton, YARMOUTH

With amazing uninterrupted views over the sea in front, this cottage is a wonderful base for family or friends to explore this beautiful, unspoilt part of the island.

Dates

From:

1 Jan 2025to31 Dec 2025
Solent Cottage - Fort Victoria

Type

Type:

Self-Catering

Norton, YARMOUTH

With amazing uninterrupted views over the sea in front, this cottage is a wonderful base for family or friends to explore this beautiful, unspoilt part of the island.

Dates

From:

1 Jan 2025to31 Dec 2025
Woodlands

Type

Type:

Self-Catering

Seaview

Nestled just a 5-minute stroll from picturesque beaches, the Seaview village shops, and the prestigious Sea View Yacht Club, Woodlands is your dream getaway.

Dates

From:

1 Jan 2025to31 Dec 2025
Bagwich House Holiday Cottages

Type

Type:

Self-Catering

Godshill

Bagwich House Holiday Cottages is surrounded by countryside in Godshill providing the perfect location for a relaxing rural escape.

Dates

From:

1 Jan 2025to31 Dec 2025
Tourism For All

Moor Farm Holiday Cottages

Type

Type:

Self-Catering

GODSHILL

We have four beautifully restored barn conversions located within Moor farm, set in idyllic countryside only 1/2 mile from the picturesque village of Godshill.

Dates

From:

1 Jan 2025to31 Dec 2025
Sea View Cottage - Fort Victoria

Type

Type:

Self-Catering

Norton, YARMOUTH

With amazing uninterrupted views over the sea in front, this cottage is a wonderful base for family or friends to explore this beautiful, unspoilt part of the island.

Dates

From:

1 Jan 2025to31 Dec 2025