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.
We have 143 self catering cottages on the Isle of Wight
From £110 per night
Farm Cottage
57182 bedroom, dog friendly self catering cottage near Ventnor.
For those looking for a peaceful and calming cottage then look no further than Farm Cottage, it's set in the delightful grounds of the owners' home and has been furnished with care...
From £110 per night
From £72 per night
The Stables
56511 bedroom, dog friendly holiday cottage close to the beach, near Ventnor.
Welcome to The Stables, a romantic getaway for two! Close to the seaside town of Ventnor, with its beautiful beachfront, you can explore this corner of the Island and then retreat ...
From £72 per night
7 nights from £713
Bentinck
57243 bedroom self catering cottage near the beach in Ventnor.
Located in a quiet spot, just moments from the vibrant high street and picturesque seafront, Bentinck offers a welcoming, beautifully refurbished home with everything you could wis...
7 nights from £713
7 nights from £1469 *
Pepita
57195 bedroom dog friendly cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1469 *
7 nights from £982
The Dairy
56313 bedroom holiday cottage near the beach in Seaview.
Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...
7 nights from £982
7 nights from £1200
The Observatory
56934 bedroom apartment with beautiful views in Seaview.
What a view! The most perfect seascape vistas will be found from this pretty apartment in the heart of the traditional seaside village of Seaview. This quirky home-from-home is the...
7 nights from £1200
From £85 per night
Sunrise and Stars
5672Dog friendly shepherds hut with a hot tub near Ventnor.
Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...
From £85 per night
7 nights from £716 *
Tangle Cottage
56694 bedroom family home close to the beach in Seaview.
Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...
7 nights from £716 *
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
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
