School Summer Holiday Cottages on the Isle of Wight
A summer on the Isle of Wight in a Classic cottage combines the ultimate holiday experience with luxury self-catering accommodation. Head out and about during the day and explore all that the Isle of Wight has to offer, and in the evening return to your own private paradise. For an unforgettable summer, we have 142 holiday homes available for you to rent. Read more
The school holidays are finally here! Now, what to do with them? A whole six weeks of entertaining the children on top of everything else can be a struggle, so why not escape for a week or two by heading west. Leave the children with the grandparents for a romantic break away to recharge your batteries, or take advantage of some true family time and have a holiday to remember in a holiday cottage.
Granny and Grandpa can come along and relax (and maybe keep an eye on the kids so you can have a quiet dinner out one evening?) Or bring your friends and their family for one big fun experience in either a large manor house or two separate cottages side by side. Holiday near the sea for bucket and spade beach days, or stay further in land to enjoy panoramic hilltop views and dog walking havens – the moors are a great place to holiday if you want to bring your four-legged friend.
Whatever you are looking for in a summer break, choose the flexibility a holiday cottage on the Isle of Wight will give you.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
142 self-catering cottages for the summer holidays on the Isle of Wight
The Beach Retreat
36652 bedroom self catering cottage near the beach in Seaview.
This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...
Price per week £466 - £704
4 Tollgate Cottage
41182 bedroom, dog friendly holiday cottage near the beach in Seaview.
4 Tollgate Cottages features an open plan living-room with wood-burning stove for cosy nights in and a door opening out to a decked area for the warmer nights. There is outdoor sea...
Price per week £487 - £730
6 Pier View Court
35592 bedroom self catering apartment near the beach in Ryde.
6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...
Price per week £489 - £776
Newlands Cottage
36373 bedroom rural self catering cottage near the beach in St Helens, Isle of Wight
Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...
Price per week £495 - £725
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...
Price per week £497 - £745
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, and just a short walk from the beach and shops. Delightfully renovated, this co...
Price per week £498 - £745
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.
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, and offers comfortable accommodation for couples and families. Enjoy al fresco ...
Price per week £500 - £745
1 Bagwich Barn
35012 bedroom, dog friendly cottage near the beach in Godshill, Isle of Wight.
A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...
Price per week £505 - £796
2 Bagwich Barn
35162 bedroom, dog friendly holiday cottage near the beach in Godshill, Isle of Wight
A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...
Price per week £505 - £796
Smugglers’ Run
39452 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight
Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. Watch the boats sail by from the privacy of the balcony off the living-...
Price per week £505 - £648