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There are many holiday cottages and houses across the Island, some in coastal locations, some in our rural areas and others in our towns, offering you the flexibility to choose the perfect location for your needs. You can even find homes with added luxuries such as swimming pools, hot tubs and ones with a seaview!
A break on the Island is the perfect escape from the hustle and bustle of everyday life. You can step back in time in beautiful conversions of historic and former working buildings, often set in stunning secluded areas. Or if you want a bit more going on right on your doorstep, our towns offer vibrant cafes and restaurants, where you can taste local cuisine; or find the ideal balance with a home in one of our villages, close to boutique shops and a cosmopolitan feel, but quiet enough to deliver a good dose of peace.
Families will enjoy holiday cottages located within our holiday parks, allowing you to use the facilities including swimming pools, playparks, nightly entertainment and family-friendly restaurants.
Of course the dog can come too! Treat the pooch to a stay at Dairyman's Cottage, a beautiful holiday cottage situated in the heart of Tapnell Farm in the West Wight. Boasting spectacular views over the countryside towards Tennyson Down and Freshwater Bay, the sunsets are amazing.
Try Somerton Farm Holiday Cottage which is located on the outskirts of the famous sailing town of Cowes. You’ll find spacious, family and dog-friendly accommodation. Or, with a range of two, three and four-bedroom self-catering accommodation, the Island Riding Centre in the heart of the Island also offers a great range of facilities for everyone.
For a classic Isle of Wight staycation, a cottage by the beach is a must. Feel like royalty with a stay at No 1 Sovereign's Gate Cottage. Set in the grounds of Osborne, Queen Vicotira’s former holiday home, you’ll have the chance to explore the beautiful grounds and Queen Victoria's private beach.
Families will love the location of National Trust Compton Farm Holiday Cottages, with the popular Compton Bay just across the road and the location is also excellent for night-time stargazing. Sea Shells by the Beach is a wing of Sea Shell House in historic Bonchurch that has been renovated to a very high standard, providing beautiful accommodation for six people across three bedrooms.
For a touch of luxury, look no further! Dolphin Cottage in the cosmopolitan village of Bembridge, promises an unforgettable and indulgent getaway thanks to its stylish interiors and prime location near the beach and village. Mottistone Manor Farmhouse self-catering holiday cottage, run by the National Trust is set in the picturesque village of Mottistone with far-reaching views across green fields to the sea.
Or for a unique stay, try Signal Point - nestled amongst the exotic plants and trees in the stunning Ventnor Botanic Garden, it has a wealth of period details and elegantly decorated rooms.
Indulge in relaxation by booking a cottage with a hot tub. Haviland Cottage was originally built as a Coach House and Stables after being extensively refurbished now boasts an impressive hot tub with mood lighting and Bluetooth speakers.
Rossiters is a beautiful thatched home set in 10 acres on the outskirts of Yarmouth, making it ideally located for walks around the rural West Wight of the Island. End the day with a warm soak in the luxurious hot tub. The Bay Colwell is situated on the beautiful west coast just a short stroll from the popular sandy Colwell Bay beach. You’ll find an indoor heated swimming pool and tennis court too.
Dive into a fun-filled family escape and book a home with a swimming pool. Rookley Farm Lodge is a five-bedroom house set in the countryside where you’ll discover an outdoor swimming pool and tennis court. Over in the West Wight, Shalfleet Manor is situated on the edge of the beautiful Newtown Estuary, a designated National Nature Reserve, meaning beautiful views to wake up to and a great place for birdwatching. The heated outdoor swimming pool and hard tennis court provide the ideal place to unwind.
Rowborough Cottage is set on a farm in a picturesque spot in the heart of the Island, with countryside views and an indoor pool perfect for a truly relaxing stay.
Make the most of our beautiful coastline and book a holiday home with a sea view.
The Old Boat House is an attractive stone cottage on the outskirts of the popular sailing village of Seaview. Set in a stunning position with views across The Solent, it’s just moments from the beach. The Sea House, also in Seaview offers a stylish, luxurious, seafront holiday home with panoramic sea views and direct access to the beach at Seagrove Bay. Or try The Beach Hut, located at Steephill Cove in Ventnor. With uninterrupted views of the sea and the charm of the peaceful cove, it's the perfect place to stay throughout the year.
If being near a local pub where you can grab a bite to eat and enjoy a couple of drinks is high on your list, then look no further.
Pheasant Cottage is set on a working farm in the pretty village of Godshill and is a short walk to the village centre, where you will find a couple of country pubs as well as cafes and restaurants. The Old School Hall in Shanklin retains the character of the converted school and is within walking distance of the several pubs, attractions and beaches that Shanklin and The Old Village are famous for. Briary Cottage is situated on the vibrant Cowes seafront and provides spectacular views out across the Solent, plus is well within easy walking distance to the variety of pubs in Cowes town.
Perfect for the whole family, these cottages are great for young children too.
Mill Cottages are tucked away within the grounds of one of the Island’s popular family attractions, Calbourne Water Mill, which is set in 10 acres of landscaped gardens on the outskirts of the West Wight. Three Gables holiday home is in the centre of the small rural village of Newbridge and has a secure garden for children to run around in, as well as beautiful panoramic country views. Therles Cottage is situated on the unspoilt southwest coast of the Island overlooking Brook Beach and just a 10-minute walk from Compton Bay, making it the perfect place for a family getaway where you can have a go at surfing too.
If you’ve got a large family or are looking for a getaway with all your friends, some of our properties are perfect for larger group bookings.
Tapnell Manor is set on the grounds of Tapnell Farm. With views out towards Tennyson Down and The Solent it’s the perfect spot for walks and making the most of neighbouring Freshwater and Yarmouth. Tiny Homes Holidays is a boutique eco-retreat near to Cowes. Discover the six unique tiny homes and enjoy a wellness retreat or team-building break for groups.
The Art Deco House is an original Art Deco house built in 1929 overlooking Sandown Bay. Offering amazing sea views (and sunrises) over the beach towards Culver Cliff, this magnificent villa takes full advantage of the cliff-top location.
If you want the peace of mind of booking with an agent, there are many reputable firms to try. With ten years of experience and many returning customers, Wight Coast Holidays has a range of holiday homes for you to choose from. Which? Recommended Classic Cottages is one of the Island-wide holiday cottage specialists, with a fabulous collection of cottages waiting for your arrival. HB Holiday Lettings offers an excellent range of quality holiday homes on the East Coast, many with beach and village locations.
If it’s a slice of the good life you are after, staying in the heart of the countryside is your best bet. Nettlecombe Farm is a working farm that offers luxurious self-catering holiday accommodation. Nestled in the heart of the rolling South Wight countryside, half a mile from the village of Whitwell, you can meet the farm animals and make the most of the popular village pub.
Surrounded by countryside but benefitting from close proximity to the coast, Brook Farmhouse Cottages provide a relaxing getaway and a great base from which to explore the Island. The Cottage at Great East Standen Manor is a historic thatched cottage on the outskirts of Newport and has been restored to the highest standard. The cottage retains much charm and character, having won the Island Conservation Award for 2006. It is situated within the grounds of a historic Manor House on 60 acres of beautiful downland with beautiful views.
Number of results: 208
, currently showing 1 to 20.
Self-Catering
ISLANDWIDE
For over 45 years, Classic Cottages have been the independent holiday cottage and glamping specialists. Still run and owned by the founding family, we pride ourselves on our local expertise in our areas.
Holiday Village
YARMOUTH
Tapnell Farm is a family owned, award-winning holiday destination set in the beautiful rural West Wight countryside, commanding the most amazing sea views and stunning sunsets!
Home to Tom’s Eco Lodge glamping and farm accommodation, Tapnell Farm…
Self-Catering
Brighstone
Charming Grade II listed Isle of Wight holiday cottage beside quiet lane on edge of pretty village of Brighstone, 1/2 mile from sea
Self-Catering
Newchurch
Self-catering cottages and luxury yurts on the Garlic Farm. A unique and beautiful place to stay with unspoilt scenery, farm walks and the Garlic Farm shop and restaurant on site with discounts for their guests. Tennis court, football pitch, games…
Self-Catering
BEMBRIDGE
HB Holiday Lettings offers an excellent range of quality holiday homes on the East Coast of the Island namely the villages of Bembridge, St Helens and Seaview. We offer both beach and village located houses of which most are pet friendly.
Self-Catering
ROOKLEY
The Lakes Rookley is set in 23 acres of beautifully manicured parkland in the heart of the Isle of Wight and makes for the perfect leafy lakeside hideaway.
Self-Catering
VENTNOR
Set in the Undercliff area of Isle of Wight National Landscape (formerly known as Area of Outstanding Natural Beauty), Woodcliffe stands in peaceful secluded terraced gardens. The house, cottage and modern apartments face south across the Undercliff…
Self-Catering
COLWELL BAY
The Bay Colwell is situated on the beautiful west coast of the Isle of Wight and just a short stroll from the wonderful Colwell Bay beach.
Self-Catering
Ventnor
Four star luxury self catering house with a Gold Award in a quiet location right next to the town centre and with panoramic sea views over the harbour and beach. Sleeps 10 in five bedrooms.
Self-Catering
TOTLAND BAY
Great location, 3 bedrooms - 2 doubles and one twin bedded room. West Wight - close to Colwell Bay, walking distance to Totland Bay and a slightly longer walk to Freshwater Bay. Quiet, pretty cottage. Lots of home comforts.
Self-Catering
Cowes
Set on a rare breed smallholding in Thorness, The Old Cowshed is a newly converted barn providing a peaceful escape with a little bit of luxury thrown in, any time of the year.
Self-Catering
Newbridge
Three Gables holiday home is in the centre of the small rural village of Newbridge on the western side of the Island.
Self-Catering
St Lawrence
Stay at Ventnor Botanic Garden, a tranquil setting, in a luxury lodge, an elegant beautifully restored Victorian cottage or charming cabins. Have a unique stay for a weekend or a week and enjoy the microclimate on the south coast of the Isle of…
Self-Catering
Bembridge
Wight Coast Holidays are a local, independent company who offer a range of self-catering holiday homes in Bembridge, Seaview, St Helens, Shanklin, Sandown, Cowes and the West Wight.
Self-Catering
BEMBRIDGE
This utterly fabulous three bed, two-bath, exceptionally loved beachside family holiday home, suitable for 6 guests is located in the coastal development of Solent Landing in Bembridge on the East coast of the island.
Self-Catering
TOTLAND BAY
Self-catering holiday let - 4-bed Norwegian log house
Self-Catering
COWES
Firefly House is a 4 bedroom luxury Victorian house with 2 parking spaces, just a few minutes walk from the historic town centre, waterfront and marinas of Cowes, home of UK yacht racing, and gateway to the Isle of Wight.
Self-Catering
NEWPORT
Pinkmead Estate & Vineyard is an incredibly unique holiday residency and one of a kind in terms of boutique self catering.
Self-Catering
St Lawrence, VENTNOR
This amazingly positioned chalet style house is a brilliant choice for a large family or group of friends as it has 4 bedrooms and sleeps up to 8 people. With French doors leading on to the wrapped around decking and a large south facing garden, an…
Self-Catering
RYDE
The Auction House is a luxury two bedroom mews house (sleeps 4) set in a tranquil courtyard in the heart of Ryde. It is just 5 minutes stroll to the beach. It forms part of a stylish conversion of Ryde's Victorian sale rooms and has been equipped…
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