Isle of Wight short breaks
The Isle of Wight is perfect for that weekend break or much-needed mid-week breather. The diversity of the island’s environments means you can find lush countryside, dramatic coastal scenes and gorgeous yacht harbours all in one place. If you want a sneaky peak of the Isle of Wight check out our new webcams.Read more
Fall in love with island life and enjoy a cosy rural retreat or a seaside escape in our luxury self-catering cottages. The isle is a perfect little getaway, only four hours from central London by car and you can be in a gorgeous holiday cottage ready to relax for a dreamy short break. Choose from an array of beautiful baby friendly and dog friendly holiday lets to cater for the whole family.
Spring and Autumn Breaks on the Isle of Wight
The mild climate of the isle creates beautiful Spring and Autumn landscapes to enjoy as summer crowds fade away. Spend three to four days surrounded by peaceful forests and serene seascapes away from the hustle and bustle.
Summer Short Breaks
Enjoy yachts, festivals, blue skies and sea breezes with a Summer on the Isle of Wight. With the island playing host to the Isle of Wight festival, Bestival and Cowes Week to name but a few, there are plenty of things to do in the Summer here. A short break in a holiday cottage is the ideal way to enjoy these festivals in style, without having to deal with the mud or rain.
Christmas on the Isle of Wight
Create magical Christmas memories with a holiday away from the mainland to really relax into the festive season. Book a short break on the Isle of Wight to discover an enchanted island filled with beautiful cottages to make your break one to remember. You may even be treated to a touch of snow.
New Year Breaks on the Isle of Wight
With celebrations taking place all over the Isle of Wight, you’re in for an amazing New Year celebration if you choose to go island-style. Close-knit communities means that everyone comes together. Have a memorable time dancing the night away with friends old and new.
Winter Breaks on the Isle of Wight
The island has a warmer climate than the mainland making winters less harsh. Ventnor supposedly benefits from the most daylight hours and the mildest climate in the UK. Although we can’t promise a tropical winter, there’s a good chance that the sun may shine for your winter holiday on the Isle of Wight. For added cosy, choose a holiday cottage with a fire on the Isle of Wight and spend your evenings curled up with a hot chocolate or a mulled wine warming your toes.
We have 97 holiday cottages available on the Isle of Wight for you to enjoy some well-deserved time off.
We have 97 self-catering cottages on the Isle of Wight available for a Short Break
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
7 nights from £776
The Shack
5634A seaside dog friendly holiday home with sea views in Cowes.
Instantly relax into your holiday and breathe in the sea air, The Shack is the perfect holiday getaway. Overlooking the waters of the Solent, start your mornings on the front deck ...
7 nights from £776
Colwell Bay Cottages
7 nights from £1234
7 nights from £617 *
Driftwood
5613A dog friendly luxury retreat with private hot tub sleeping 4.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...
7 nights from £617 *
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 £617 *
Escape Away
5612A luxury retreat with private hot tub and use of swimming pool.
New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...
7 nights from £617 *
7 nights from £1932
Tamarisk House
55164 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...
7 nights from £1932
7 nights from £1181 *
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...
7 nights from £1181 *
From £162 per night
Lazydays Hideaway
53811 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...
From £162 per night
7 nights from £900
Weirside Cottage
53202 bedroom, dog friendly holiday cottage near the beach near Yarmouth.
As pretty as a picture, feast your eyes on Weirside a stunning Grade II Listed cottage at the heart of the idyllic island village of Brighstone, just half mile from the sea and the...
7 nights from £900
7 nights from £428
Berry Cabin
52862 bedroom, dog friendly, self catering cottage in Seaview, Isle of Wight.
What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...
7 nights from £428
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
