Luxury Cottages in May on the Isle of Wight
Put a spring in your step and stay in a luxury self-catering cottage on the Isle of Wight this May. Whether it's a May half-term holiday, a short break over a May bank holiday or a much-anticipated getaway ahead of the summer crowds, our portfolio of 57 available properties provide an idyllic base. Look forward to adventure, fun and total comfort all with the Isle of Wight's stunning backdrop. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.See our range of 57 available cottages in May on the Isle of Wight
7 nights from £1369
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1369
7 nights from £986
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 £986
7 nights from £1135
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 £1135
7 nights from £1888 *
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 £1888 *
7 nights from £1249
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 £1249
7 nights from £963 *
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 £963 *
7 nights from £1155
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 £1155
7 nights from £798 *
Escape Away
56122 bedroom self catering cottage near the beach in Freshwater.
Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...
7 nights from £798 *
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £798 *
Driftwood
56132 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do. Th...
7 nights from £798 *
Colwell Bay Cottages
7 nights from £1595
Whoever you want to spend your dream holiday with on the Isle of Wight, be it a solo retreat, family holiday or catch up with friends, the choice is yours. One thing is for certain though: where you want to spend it. At Classic Cottages, we offer the finest quality self-catering accommodation around. With each property carefully selected onto our books, we personally inspect all of our cottages to maintain the highest standards.
From cosy one-bed retreats to spacious family-friendly properties, we have a wide range of properties ready and waiting to welcome you. Fall in love with a beach-side cottage with spectacular sea views, or luxuriate in a rural retreat with a beautiful garden perfect for long afternoons in the sunshine. Pick a private escape set back away from it all, or choose a bolthole close to all the local amenities. The holiday of your dreams awaits.
May Cottages on the Isle of Wight
At Classic Cottages, we understand the importance of accommodation in making or breaking your holiday. That's why all of our self-catering cottages have been handpicked; personally inspected to make sure only the best make it onto our books. You needn't worry about cramming everything into your luggage either. Each of our cottages is equipped with a full inventory. Everything from your bed linens to your morning coffee pot to enough crockery is provided, so you needn't worry about a thing.
