Clevelands Country House, Isle of Wight

06/09/2026

The group chat has 147 messages.

Three people haven't replied.

Someone can only do alternate weekends.

And nobody wants the sofa bed.

We can't help with the group chat.

We can help with the house.

Clevelands gives groups of 8 plenty of room to spend an autumn weekend together, with five bedrooms, a large kitchen, cosy dining room and Isle of Wight countryside on the doorstep.

Sleeps up to 10.

Explore now...
https://www.clevelandsiow.co.uk/property/clevelands-country-house-isle-of-wight

05/09/2026

There comes a point when getting everyone together becomes harder than it ought to be.

October gives you a rather good excuse.

Clevelands Country House in Wroxall sleeps up to 10 across five bedrooms, with plenty of room for families and friends to spread out — and plenty of space to come back together.

Spend the day walking, exploring the Island or finding somewhere good for lunch. Come home, cook together, open something nice and enjoy an evening when nobody has to rush off.

October is also a wonderful time to explore the Isle of Wight on foot, with the Autumn Walking Festival taking place from 3–11 October.

Clevelands currently has availability from 1–23 October.

🐾 Up to two dogs welcome when booking direct.
⛴️ Discounted car ferry travel can be arranged for direct guests.

Planning an October Isle of Wight get-together? Check availability and book direct.

www.clevelandsiow.co.uk

03/09/2026

Grab the boots — October is walking month on the Isle of Wight.

The Autumn Walking Festival returns from 3–11 October 2026, with guided walks across the Island and routes for different interests and abilities.

Make a few days of it and choose the Isle Getaway base that suits you.

Clevelands Country House — bring the walking gang or family together. Sleeps up to 10.

Hunter Heights — peaceful adults-only countryside base, ideal for two.

Jersey Cottage — stay in Cowes and explore different parts of the Island.

And while Dubarry Downs is already occupied for much of the Festival itself, it has later October availability if you'd prefer your walking break once the Festival crowds have gone.

Boots packed? October awaits.

https://www.clevelandsiow.co.uk/search

Owner-managed self-catering holiday homes in Cowes and Wroxall, Isle of Wight. Thoughtfully maintained stays for families, couples and short breaks.

02/09/2026

Getting eight people together can be the hardest part.

Once you've managed that, we'll provide the house.

Clevelands Country House is made for autumn weekends with family or friends — five bedrooms, a big kitchen for cooking together and a cosy dining room where dinner can turn into drinks, stories and another bottle being opened.

Outside, you've got the Isle of Wight countryside to explore.

Inside, you've got somewhere warm to come home to.

Sleeps up to 10, but wonderfully spacious for 8.

Autumn stays now available.

Book direct and ask us about discounted car ferry travel from Southampton.

ENQUIRE 👇
https://www.clevelandsiow.co.uk/property/clevelands-country-house-isle-of-wight

Owner-managed self-catering holiday homes in Cowes and Wroxall, Isle of Wight. Thoughtfully maintained stays for families, couples and short breaks.

30/08/2026

One of the Isle of Wight's most loved festive events returns this December.

From 3rd–6th December 2026, the beautiful village of Brighstone is transformed as its historic church fills with hundreds of beautifully decorated Christmas trees, accompanied by festive music, local crafts and a wonderful community atmosphere.

It's one of those special Island traditions that visitors return to year after year.

Make a weekend of it by exploring festive Ventnor, enjoying coastal walks, discovering cosy cafés and experiencing the Island at its most magical.

Whether you're staying in Dubarry Downs Annexe or Clevelands Country House in Wroxall, Brighstone is an easy drive away and makes a wonderful festive day out.

🏡 Stay with Isle Getaway Escapes

🚢 Discounted ferry crossings available when you book direct.

Plan your festive Isle of Wight getaway and book early for the best choice of dates.
https://www.clevelandsiow.co.uk/search

29/08/2026

There comes a point when getting everyone together becomes harder than it ought to be.

October gives you a rather good excuse.

Clevelands Country House in Wroxall sleeps up to 10 across five bedrooms, with plenty of room for families and friends to spread out — and plenty of space to come back together.

Spend the day walking, exploring the Island or finding somewhere good for lunch. Come home, cook together, open something nice and enjoy an evening when nobody has to rush off.

October is also a wonderful time to explore the Isle of Wight on foot, with the Autumn Walking Festival taking place from 3–11 October.

Clevelands currently has availability from 1–23 October.

⛴️ Discounted car ferry travel can be arranged for direct guests.

Planning an October Isle of Wight get-together? Check availability and book direct.
Need more space, look at our one bedroom apartments too...

www.clevelandsiow.co.uk

27/08/2026

We know. It's still August.

But when ten people need to agree on Christmas plans, August suddenly doesn't seem quite so early.

Clevelands was made for getting everyone under one roof.

Five bedrooms. A big kitchen. Space for ten around the table. Countryside outside the door.

And, importantly, enough room for everyone to spread out when they've had quite enough family time for one afternoon!

Christmas 2026 at Clevelands is now available to book.

Direct-booking guests can also ask us about discounted Isle of Wight car ferry travel.

🎄 Christmas 2026
🏡 Sleeps 10
📍 Isle of Wight

25/08/2026

Autumn on the Isle of Wight has a completely different rhythm.

The summer crowds begin to thin, walking becomes a pleasure again and there's something very satisfying about coming back from a day outdoors to a house full of people you actually want to spend time with.

Clevelands sleeps up to 10, making it particularly suited to family gatherings, friends, walking groups and multi-generational stays.

And autumn is only the beginning.

October half term is approaching — and we're now taking bookings for Diwali, Christmas and New Year too.

If you've ever fancied gathering everyone together on the Isle of Wight for the festive season, now is a very good time to start planning.

23/08/2026

October half term hols, Diwali or Autumn/ Winter Weekends— bring the generations together.

Bring the grandparents. Bring the teenagers. Bring the walking boots.

At Clevelands Country House there are five bedrooms, a big family kitchen, space for ten around the dining table and enough room for everyone to have a little space of their own too.

Need more room? We have two additional one-bedroom apartments onsite too. Perfect for Grandparents that just need a space of their own, away fron the excitement!

Spend the day exploring the Island, walking the downs or visiting one of our historic attractions — then come home, cook something good and settle in for the evening.

For larger and multi-generational families, that's often the best bit: actually having time together.

🏡 Sleeps up to 10 or add on some more...
🛏️ Five bedrooms, add more with our two one bedroom apartments on site.
🚗 Parking for three cars and another two...
⛴️ Discounted car ferry fares available to direct guests

October half-term hols, Diwali and Family weekends stays now available.

Need more room? We have two additional one-bedroom apartments onsite too. Perfect for Grandparents that just need a space of their own, away fron all the excitement!

20/08/2026

Autumn weekends ✔
Half term ✔
Diwali ✔
Christmas ✔
New Year ✔

Which would you choose?

www.clevelandsiow.co.uk