Cottages on the Isle of Wight
Setting off on holiday to the Isle of Wight often feels like you’re going on a grand adventure. Sit back and relax on a short ferry crossing (don't forget you can make use of our exclusive ferry discounts!), and arrive on the Island to a world of nature, gorgeous scenery and plenty of fresh sea air (and fresh seafood). Discover the many gardens, historic buildings, beaches, and walks that can be found across this beautiful island. An Isle of Wight holiday is like no other, and we have a handpicked collection of gorgeous self catering holiday cottages for you to discover…Read more
There’s plenty for you to do, whether you’re after the picture perfect sunset or an outdoor adventure. We’ve compiled an Isle of Wight Bucket List for you to take your pick of holiday adventures! Why not try something new? There’s kayaking, paragliding, sailing or coasteering for the adventurous, gentle coastal walks and plenty of family friendly attractions. And don't forget the many Isle of Wight festivals!
And as for accommodation, we have dog friendly cottages, cottages with a hot tub, beautiful homes perfect for a family gathering or gorgeous retreats for a romantic getaway. Find your perfect holiday cottage in the Isle of Wight here…
Check out our webcams in Ryde and Freshwater to see what awaits you.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 144 self catering cottages on the Isle of Wight
7 nights from £908
Inglefield
5637Dog friendly holiday cottage with 4 bedroom near the beach in St Helens.
This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...
7 nights from £908
7 nights from £650
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £650
7 nights from £776
The Shack
5634A seaside dog friendly holiday home with sea views in Cowes.
Instantly relax into your holiday and breathe in the sea air, The Shack is the perfect holiday getaway. Overlooking the waters of the Solent, start your mornings on the front deck ...
7 nights from £776
7 nights from £617 *
Driftwood
5613A dog friendly luxury retreat with private hot tub sleeping 4.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...
7 nights from £617 *
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
Colwell Bay Cottages
7 nights from £1234
7 nights from £617 *
Escape Away
5612A luxury retreat with private hot tub and use of swimming pool.
New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...
7 nights from £617 *
7 nights from £508
Blakesley Cottage
55652 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...
7 nights from £508
Bagwich House
7 nights from £1524
7 nights from £1932
Tamarisk House
55164 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...
7 nights from £1932
7 nights from £1181 *
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...
7 nights from £1181 *
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
