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 143 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 143 self-catering cottages on the Isle of Wight available for a Short Break
The Battenburg Studio
36641 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...
Price per week £240 - £620
The Beatrice Studio
36661 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...
Price per week £240 - £620
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!
The Sail Loft
41071 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous top floor one bedroom apartment has spectacular sea views over the rooftops across the Solent and is just a few minutes from Seaview village and the beach. Newly dec...
Price per week £250 - £475
West Flatlet
36921 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...
Price per week £252 - £420
Sea Song
39401 bedroom self catering apartment near Ventnor, Isle of Wight
Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...
Price per week £265 - £485
Mariners Cove
36281 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...
Price per week £266 - £460
Berryl Mead View
39061 bedroom self catering cottage near Ventnor, Isle of Wight
Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...
Price per week £275 - £536
The Ivy
36711 bedroom, dog friendly holiday apartment near the beach in Shanklin, Isle of Wight.
The Ivy is a compact double bedroom annexe offering comfortable accommodation for a couple seeking a relaxing island escape. Ideally located, with Shanklin village and beach a shor...
Price per week £295 - £510
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.
Afton Lodge
35721 bedroom, dog friendly cottage near the beach near Old Freshwater, Isle of Wight.
If a quintessentially English cottage is what you're after for your holiday, look no further than Afton Lodge. Set in Old Freshwater, the lodge boasts a thatched roof, stable door ...
Price per week £335 - £650
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