Isle of Wight Cottages
The Isle of Wight benefits from the best parts of the British coast and countryside. Our exclusive collection of Isle of Wight cottages have been handpicked and inspected by our team of local experts. Bring your four legged friend for a run on the island’s beaches and stay in one of our dog friendly cottages or plan a big family getaway for Cowes Week in the summer. Take a break for two and relax by the sea in Ventnor or get active with a cycling or walking holiday on the Isle of Wight.
We take the hassle out of travel by sorting out the ferry arrangements for you so hop on board and be transported to this pretty isle with dramatic coastlines, beautiful forests, a wonderful history and of course, the best pick of holiday cottages.With its iconic Needles and white cliffs, the Isle of Wight is a world away from the mainland. Hop on a ferry and be transported to a pretty isle with dramatic coastlines, beautiful forests and a wonderful history left by its Victorian visitors which can still be seen today.
This 23 by 13 mile island is a hidden gem of escapism in the United Kingdom. The Isle of Wight is small but mighty. The size of the island makes it easy to get around once you’re here and the proximity to the mainland makes it even easier to get to the island in the first place. Around 3 hours from London, the Isle of Wight is the perfect weekend getaway if you’re looking for a relaxing short break.
Choosing a luxury holiday cottage on the Isle of Wight is a tough decision. We've welcomed Wight Locations into our fold and kept the office on the island filled with knowledgeable local staff to help with your holiday cottage needs. There are beautiful large properties for all the family in the popular village of Seaview. Find a couples bolthole on the sea front at Shanklin. Go for a traditional thatched cottage or a thoroughly modern family apartment, it’s up to you. We have plenty of dog friendly and family friendly cottages to choose from. The island is particularly great for dogs: many of the beaches and restaurants are dog friendly year round, just like our properties across Cornwall, Devon, Dorset, Somerset and Hampshire.
Regardless of where your self catering cottage is, you’ll be able to get around the island easily. In South Wight, take long walks along the promenade at Sandown, Shanklin and Ventnor, explore the magic of Shanklin Chine and find some fresh fish to take home for dinner at Ventnor Haven. Stop at the pretty chocolate box village of Godshill for a classic cream tea and a look around the famous Godshill model village.
In West Wight, get on your walking boots for a stomp along the coastal path. Take in the dramatic views of Freshwater Bay, the iconic Needles and Totland Bay stopping off for lunch at one of the traditional pubs en route. The north of the island is a sailors paradise, Cowes plays host to the annual sailing festival Cowes Week in August, a must for all sailing fanatics. East Cowes was the former home of Queen Victoria who loved the area so much she built Osborne House, a great day out for all. East Wight is home to gorgeous valley views and plenty of things to do. The majority of the population live in the east so you’ll find eateries, vineyards, roman villas and more on this side of the island. A great place to use as a base for your holiday to the Isle of Wight.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
198 Luxury self catering Isle of Wight cottages.
The Cadogan Apartment
36671 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...
Price per week £360 - £940
62 Buddleia Cottage
35662 bedroom self catering cottage near the beach in Seaview.
Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...
Price per week £309 - £670
The Worsley Apartment
36821 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...
Price per week £360 - £940
3 Kings House
35442 bedroom, rural self catering cottage near the beach in Bembridge, Isle of Wight.
Take a few steps up to the entrance, and you'll find yourself in 3 Kings House, a ground floor apartment in a small development. The property is just a short walk from Bembridge Ha...
Price per week £295 - £630
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.
53a Howgate Road
37492 bedroom, dog friendly apartment near the beach near St Helens, Isle of Wight.
This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...
Price per week £295 - £695
The Crows Nest
36702 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
The Crow's Nest is a second floor apartment of a Victoria property in the historic village of Seaview. Simply furnished but with wonderful views over the village rooftops to the So...
Price per week £295 - £595
35 Cross Street
35502 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...
Price per week £303 - £680
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...
Price per week £309 - £660
61 Drake Cottage
35652 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...
Price per week £309 - £670
The Lobster Pot
36722 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...
Price per week £312 - £690
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details in the post two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!