Cottages on the Isle of Wight
From the short ferry crossing (guests can receive a discount up to 25% with us) that delivers you to the sun-soaked shores to the caught-in-time atmosphere of the seaside towns, setting off for a stay in a gorgeous self-catering holiday cottage on the Isle of Wight is a true adventure. Our collection of wholesome home-from-homes boasts something special for everyone, from fabulous dog-friendly cottages with sea views to magical shepherd’s huts and safari tents in a little pocket of Island paradise. Whether you’re dreaming of a short break in a cosy cottage with a hot tub or a family-friendly escape for a classic summer holiday by the sea, the Isle of Wight is the perfect holiday destination for all. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 194 self catering cottages on the Isle of Wight
Reayrt Ny Marrey
210Charming Manx cottage in the picturesque village of Kirk Michael
Nestled on the island's western corner, Reayrt Ny Marrey is perfectly placed in Kirk Michael, known for its captivating shorelines, long sandy beaches, and dramatic woodland and gl...
Bwaane Jiass
30Bwaane Jiass is the smallest of one of three cottages located together in a quiet, peaceful location
Bwaane Jiass is the smallest of one of three self catering holiday cottages located together in a quiet, peaceful location at the end of a private driveway in the beautiful country...
Royal 1
98Located in Ramsey, Royal 1 is conveniently located a matter of minutes walk from the town centre
Royal 1 is self-catering annex adjoined to the owner's main house, located just minutes from Ramsey town centre by foot. The town of Ramsey with its independent shops and cafes ...
The Tower
142The Tower is a beautiful converted 17th century outhouse
The Tower is situated in rolling countryside in the west of the Isle of Man, just 5 minutes from Peel. Sleeping 2 and offering use of a private hot tub, this property is perfect fo...
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Close Taggart - Thie Rhennie
39Providing the perfect setting for a special break for two, Thie Rhennie is one of two cottages
We know you will be delighted when you arrive at Close Taggart. These two gold award holiday cottages, Thie Rhennie ("House of Ferns") and Thie Lough ("House of the ...
Close Taggart - Thie Lough
38Providing the perfect setting for a special break for two, Thie Lough is one of two identical cottag
We know you will be delighted when you arrive at Close Taggart. These two gold award holiday cottages, Thie Rhennie ("House of Ferns") and Thie Lough ("House of the ...
Cronk Breck Cottage
48A charming single level home in Ballaugh, a peaceful village in the north west of the Isle of Man.
Cronk Breck is a bright and comfortable single level self catering holiday home in Ballaugh, Isle of Man. Cronk Breck is the ideal base for a couple's visit to the island. The h...
Curlew Cottage
51Curlew cottage is a charming 18th century one bedroom traditional Manx stone cottage in the heart of
Curlew cottage is a charming 18th century one (double) bedroom traditional Manx stone cottage which retains some original features a stone fireplace and open beam ceilings in loung...
Heron at Trail Lodge
177Stylish studio apartment located in an idyllic national glen.
Heron at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasalla...
Drakes at Trail Lodge
176Stylish studio apartment located in an idyllic national glen.
Drakes at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasall...
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.
Holidays on the Isle of Wight
Wind down and enjoy the relaxed pace of Island living with a holiday on the Isle of Wight. Golden beaches promise sun-soaked beach days, historic houses offer a fascinating glimpse into the Island’s past, and patchwork interior invites you to pull on your walking boots for long, leisurely walks - there’s even an annual festival!
Beaches on the Isle of Wight
Settle into island life as you discover beaches around every salt-kissed corner of the Isle of Wight Coastal Path, from secret coves only accessible by boat to great sweeps of sand that call for long days lazing under the sun. With turquoise waters and breathtaking cliffs, Freshwater Bay is a popular choice for scenic sun worshipping (our webcam has gorgeous views across the beach), while Ventnor promises a wonderfully traditional day by the sea with ice creams, paddling pools, and your very own microclimate to enjoy.
Things to do on the Isle of Wight
Packed with ancient forts, family-friendly attractions, and over 500 miles of designated footpaths, the Isle of Wight is a veritable playground with countless things to do during your stay. Walking from Freshwater Bay to The Needles is a fantastic way to explore one of the Island’s most iconic landmarks, with local boat trips offering the opportunity to see the stacks from the sea. Osbourne House is another favourite spot to explore, with royal rooms and sweeping grounds that make it easy to see why Queen Victoria relished her time here. The Isle of Wight is also home to some of the country’s biggest festivals, from music festivals and garlic celebrations to the famous sailing races during Cowes Week.
Places to eat on the Isle of Wight
Making the most of the Island’s microclimate, food producers have put the Isle of Wight firmly on the foodie map, with the Garlic Farm and Isle of Wight Tomatoes both providing world-class ingredients for the Island’s restaurants and cafés. In Seaview, you’ll find a wide range of fabulous eateries, from Michelin recommended restaurants to award-winning pubs full of traditional charm, while Yarmouth promises some of the best sea view restaurants and cafés on the Island.
