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
177 Luxury self catering cottages on the Isle of Wight
7 nights from £352
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...
7 nights from £352
7 nights from £354
Yardley
36972 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £354
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 £357
The Coach House
40382 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight
One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...
7 nights from £357
7 nights from £357
The Stables
40372 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight
Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...
7 nights from £357
7 nights from £358
Quiet Corner Cottage
36462 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Quiet Corner is a modestly furnished, comfortable cottage situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests it's tucked away...
7 nights from £358
7 nights from £359
23 Tollgate Cottages
35352 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...
7 nights from £359
7 nights from £359
Seascape
39432 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...
7 nights from £359
7 nights from £361
5 Sandpipers
35572 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...
7 nights from £361
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 £364
Dairy Cottage
39122 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...
7 nights from £364
7 nights from £364
Orchard Cottage
39362 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...
7 nights from £364