Isle of Wight Holiday Cottages
Our exclusive Isle of Wight cottages are handpicked and inspected by our team of local island experts. From dog friendly homes with enclosed gardens to luxury cottages with a hot tub, we’ve selected properties with great holidays in mind. With some of the best coast and countryside in Britain, the Isle of Wight is perfect for a romantic break for two or a family gathering with pets and all. Check out our webcams in Ryde and Freshwater to see what awaits you.Read more
About the Isle of Wight
Small but mighty, this 23 by 13 mile island is a hidden gem of escapism in the United Kingdom. The size of the island makes it easy to get around once you’re here and the proximity to the mainland makes it even easier to get here in the first place. Around 3 hours from London, the Isle of Wight is perfect for a weekend getaway in a luxury cottage if you’re looking for a relaxing short break.
We know this island like no one else, and if you’re after some local tips we’ve got plenty, as we document the best things to do on the Isle of Wight on our blog. From top sunset spots to Christmas markets, we’ve found some real island gems for your visit. Whether you’re after a hive of activity or something more off the beaten track, take a look at our blog or speak to our Isle of Wight team for some hints from the experts.
Where to stay on the island
To make your holiday special, we've picked out a great selection of self catered homes across the island for whatever you need. If you're getting the family together and need a place fit for a big group, we have plenty of large family friendly Isle of Wight cottages to accommodate you all. Or for a more romantic feel, tuck yourself away in one of our cottages for two away from it all on the island.
This is a great destination for holidays with pets too, with plenty of dog friendly beaches and pubs welcoming dogs all year round. Most importantly, we’ve got plenty of dog friendly cottages on the Isle of Wight just waiting to welcome you and your furry friend.
Add a little luxury
Our Isle of Wight holiday cottages with a pool might be just what you need, and many properties come equipped with a private hot tub as well. Sink back and embrace the relaxing island lifestyle in a luxury holiday cottage – you’ve earned it.
For an even more relaxing break look no further than a holiday cottage near the beach, with a sunbathe or a sea swim only steps away. Wherever you stay on the Isle of Wight you won’t be too far from the sea but if it’s sandcastles and surfboards on your mind, choosing one of our self catering spots near the beach is a must.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
218 Luxury self catering cottages on the Isle of Wight
7 nights from £335
Afton Lodge
35721 bedroom, dog friendly cottage near the beach near Old Freshwater, Isle of Wight.
If a quintessentially English cottage is what you're after for your holiday, look no further than Afton Lodge. Set in Old Freshwater, the lodge boasts a thatched roof, stable door ...
7 nights from £335
7 nights from £360
The Cadogan Apartment
36671 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...
7 nights from £360
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20% off
20 Dec 2018 - 27 Dec 2018
£659.97 £528.00
7 nights from £309
62 Buddleia Cottage
35662 bedroom self catering cottage near the beach in Seaview.
Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...
7 nights from £309
7 nights from £360
The Worsley Apartment
36821 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...
7 nights from £360
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £251
Trevessa
36872 bedroom, dog friendly holiday cottage near the beach in Ventnor, Isle of Wight.
With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...
7 nights from £251
7 nights from £290
The Beach Retreat
36652 bedroom self catering cottage near the beach in Seaview.
This stylish, compact seaside bungalow is located in a front row position with wonderful views across the Solent. It would ideally suit a family with young children or a couple loo...
7 nights from £290
7 nights from £295
3 Kings House
35442 bedroom, rural self catering cottage near the beach in Bembridge, Isle of Wight.
Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...
7 nights from £295
7 nights from £295
53a Howgate Road
37492 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.
This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...
7 nights from £295
7 nights from £295
The Crows Nest
36702 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...
7 nights from £295
7 nights from £303
35 Cross Street
35502 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...
7 nights from £303
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.