Isle of Wight Holiday Cottages
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 and arrive on the Island to a world of nature, gorgeous scenery and plenty of fresh sea air. 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.
155 Luxury self catering cottages on the Isle of Wight
7 nights from £540
Buckland Cabin
48531 bedroom cabin near the beach in Seaview, Isle of Wight.
Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...
7 nights from £540
7 nights from £2000
Cara Cottage
48465 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...
7 nights from £2000
7 nights from £840
Daisy Cottage
48242 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...
7 nights from £840
7 nights from £1250
The Gate
48132 bedroom, dog friendly apartment near the beach in Freshwater, Isle of Wight.
Located a stone's throw from Freshwater Bay, The Gate is a superb newly renovated ground floor apartment by the sea. This simply wonderful retreat has been designed and decorated t...
7 nights from £1250
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £1622
Hillside
47895 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
A beautifully renovated house tucked away in The Close, just a few minutes from idyllic Seagrove Bay, Hillside is a truly wonderful place to base yourself on the Isle of Wight. Lig...
7 nights from £1622
7 nights from £935
Old Bembridge House
47913 bedroom, dog friendly holiday cottage near the beach in Bembridge.
Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, this wonderful Classic Cottage has all the makings of a perfect holiday idyll. Laid across th...
7 nights from £935
7 nights from £2184
Harbour View
47314 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...
7 nights from £2184
7 nights from £800
Starboard Side
47362 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...
7 nights from £800
7 nights from £850
The Tap Room
46993 bedroom self catering cottage near the beach in Freshwater, Isle of Wight.
If you are looking for a truly unique island getaway then look no further, welcome to The Tap Room. Set within Golden Hill Fort, a beautifully restored Grade 1 listed hexagonal for...
7 nights from £850
7 nights from £2200
Elmscott
46643 bedroom self catering cottage near the beach in Yarmouth, Isle of Wight.
Welcome to Elmscott a beautifully appointed and luxuriously spacious retreat offering a wonderfully chilled out holiday experience, complete with heated pool within large, manicure...
7 nights from £2200
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.