Perfect for family holidays, shared celebrations and group breaks on the Isle of Wight. Our flexible self-catering holiday homes are also well suited to multi-generational and extended family breaks, offering space to spend time together comfortably.
Our homes are designed for memorable family breaks, shared celebrations and spacious group accommodation on the Isle of Wight.
Family and group holidays work best when there’s space to relax, flexible layouts and a setting that suits time together. Our Isle of Wight holiday homes are owner-managed and thoughtfully set up for family gatherings, multi-generational stays and shared celebrations.
Whether you’re looking for a countryside base with room to spread out or a central Cowes location close to sailing and events, the properties below offer the most suitable options for families and groups travelling together.
Our holiday homes are chosen for space, flexibility and location — ideal for families travelling together, multi-generational stays, and groups who want shared time with the option of privacy when needed.
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Clevelands Country House, Wroxall
- Ideal for larger family groups
- Ability to increase guest numbers by adding on-site apartments
- Perfect for grandparents who want peace and separate space
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Jersey Cottage, Cowes
- Best for families with older children or adult groups
- Central location near ferries, town and sailing activity
Two well-suited options depending on space and location preference.
Clevelands Country House, Wroxall
As the lead home, with the option to add one or two on-site apartments — ideal for grandparents or couples who want peace and their own space
Jersey Cottage, Cowes
This home works particularly well for families with older children or adult groups who want to be close to town, ferries and sailing activity.
When travelling as a family or group, finding the right balance between shared time and personal space makes all the difference. Whether you’re bringing generations together, attending a wedding, or planning a relaxed group break, choosing accommodation that genuinely fits your needs helps everyone enjoy the stay.
With flexible options at Clevelands Country House — including the ability to add on-site apartments — and a central Cowes base at Jersey Cottage, Isle Getaway Escapes offers thoughtful, well-located places to stay that suit different group dynamics, without compromising on comfort or calm.
For larger family groups, you may be able to add one of our nearby one-bedroom apartments to your stay
This can work well for grandparents, adult children or guests who appreciate a little more privacy while staying close together.
Availability varies and this option is best discussed before booking.
Isle Getaway Escapes properties are also well suited to wedding guests attending celebrations at nearby venues on the Isle of Wight, offering comfortable, flexible accommodation for couples, families and groups travelling together.
Wroxall
Our Wroxall properties, including Clevelands Country House and the on-site apartments, are particularly convenient for guests attending weddings at Appuldurcombe House.
Cowes
Jersey Cottage in Cowes is a popular choice for wedding guests celebrating at Northwood House, offering a central base with easy access to venues, transport links and local amenities.
What is the maximum number of guests at Clevelands Country House?
The maximum occupancy at Clevelands Country House is 10 guests in total, including adults, children and babies. This limit is set in line with our fire safety regulations and property insurance and cannot be exceeded under any circumstances.
Are dogs permitted at Clevelands Country House?
Yes, by prior arrangement. Well-behaved dogs may be considered at Clevelands Country House when agreed in advance. Please contact us before booking to discuss suitability and conditions.
What is the maximum number of guests at Jersey Cottage?
The maximum occupancy at Jersey Cottage is 8 guests in total, including adults and children. This limit is set in line with our fire safety regulations and property insurance and cannot be exceeded under any circumstances. The cottage is best suited to families with older children due to the layout and stairs.
Are dogs permitted at Jersey Cottage?
No. Jersey Cottage does not accept dogs, as the property is not suitable for pets.
Which property is best for larger family groups?
Clevelands Country House is our largest holiday home and is best suited to extended families and group stays who value generous space, shared living areas and a countryside setting.
Can we add extra accommodation for larger family groups?
For some larger family groups, it may be possible to add one of our nearby one-bedroom apartments at Clevelands to the booking. This can work well for grandparents, adult children or guests who appreciate additional privacy while staying close together. Availability varies and this option is best discussed before booking.
Are these homes suitable for multi-generational family stays?
Yes. Our family and group holiday homes are well suited to multi-generational stays, offering flexible layouts and space to spend time together comfortably.
Are the properties suitable for parties, stag or hen groups?
No. Our holiday homes are located in residential areas and are not suitable for parties, stag or hen groups. We ask all guests to respect our neighbours and enjoy the properties as relaxed holiday homes rather than event venues.