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. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 86 self-catering cottages on the Isle of Wight available for a Short Break
7 nights from £648 *
48 Solent View
58283 bedroom self catering cottage with sea views in Seaview.
Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...
7 nights from £648 *
7 nights from £1050
Pucks Oak
56984 bedroom, dog friendly holiday cottage with sea views in Seaview.
Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...
7 nights from £1050
7 nights from £372
The Studio
57531 bedroom, dog friendly, cosy cottage near Ryde.
Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...
7 nights from £372
The Old Dairy
7 nights from £1037
7 nights from £721
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £721
7 nights from £1498 *
Pepita
57195 bedroom, dog friendly holiday cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1498 *
7 nights from £991
The Dairy
56313 bedroom self catering cottage near the beach in Seaview.
Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...
7 nights from £991
From £85 per night
Sunrise and Stars
5672Dog friendly shepherds hut with a hot tub and use of pool, near Ventnor.
Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...
From £85 per night
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £728 *
Tangle Cottage
56694 bedroom self catering cottage near the beach in Seaview.
Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...
7 nights from £728 *
7 nights from £726 *
Inglefield
56374 bedroom, dog friendly holiday cottage near the beach in St Helens.
This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...
7 nights from £726 *
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 86 holiday cottages available on the Isle of Wight for you to enjoy some well-deserved time off.
