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.
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 154 holiday cottages available on the Isle of Wight for you to enjoy some well-deserved time off.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
We have 154 self-catering cottages on the Isle of Wight available for a Short Break
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...
Price per week £345 - £842
Yardley
36972 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
Price per week £347 - £745
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!
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview.
2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...
Price per week £348 - £735
Quiet Corner Cottage
36462 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Quiet Corner is a modestly furnished, comfortable cottage situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests it's tucked away...
Price per week £351 - £806
9 Tollgate Cottage
37552 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Number 9 has an open plan living-room with wood-burning stove for cosy nights in and door opening out to a decked area for the warmer nights. There is seating on the decking to rel...
Price per week £351 - £730
17 Tollgate Cottage
37572 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Number 17 is located at the end of the development looking out to the shared communal grounds and Seaview Nature Reserve. There is a downstairs twin bedroom with a walk-in shower a...
Price per week £351 - £730
18 Tollgate Cottage
37582 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Number 18 is a two bedroomed chalet on the small Tollgate holiday complex on the Seaview Duver. These are ideal to rent out for larger families as you can rent next door and other ...
Price per week £351 - £730
23 Tollgate Cottages
35352 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...
Price per week £351 - £745
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
Seascape
39432 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...
Price per week £352 - £796
5 Sandpipers
35572 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple and small family. The sit...
Price per week £353 - £745