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 107 self catering cottages on the Isle of Wight
7 nights from £1521 booking fees included
St Hubert's Lodge
60573 bedroom, dog friendly self catering cottage near Yarmouth.
Surrounded by tranquil countryside on the edge of the Isle of Wight National Landscape and close to the charming seaside island towns of Yarmouth and Cowes, St Hubert's Lodge is a ...
7 nights from £1521
7 nights from £853 * booking fees included
Grey Gulls
61594 bedroom dog friendly self catering cottage with sea views in Seaview.
This beautifully presented, semi-detached, three-storey townhouse is set in the sought-after village of Seaview, just a stone's throw away from stunning beaches with crystal clear ...
7 nights from £853 *
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £513 booking fees included
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £513
7 nights from £850 booking fees included
Wickings
61013 bedroom, dog friendly holiday cottage near the beach in Ventnor.
Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...
7 nights from £850
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £818 * booking fees included
Little Field
61233 bedroom, dog friendly holiday cottage near the beach near Ryde.
Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...
7 nights from £818 *
7 nights from £905 * booking fees included
The Police House
60514 bedroom, dog friendly holiday cottage near the beach in Seaview.
Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...
7 nights from £905 *
7 nights from £549 booking fees included
Seascape
59442 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
Located in the cosmopolitan town of Ventnor within a Victorian townhouse, Seascape is a modern two-bedroom, ground floor, apartment with spectacular sea views overlooking the bay. ...
7 nights from £549
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20% off
25 Jul 2026 - 1 Aug 2026
£873.00 £711.00 booking fees included
7 nights from £1047 booking fees included
Maybury
59913 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Your dream coastal escape awaits in Seaview! Escape to elegant Maybury and stay in this beautifully styled home with sandy beaches and village amenities on your doorstep. This blis...
7 nights from £1047
7 nights from £850 booking fees included
Fenders
59873 bedroom, dog friendly cottage near the beach in Totland.
Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...
7 nights from £850
7 nights from £1098 booking fees included
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1098
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.
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.
