Isle of Wight Cottages for May Half-Term
Blue skies, warm sunshine and long days filled with whatever you please. May half-term holidays are an excellent way to welcome summer and slip into a relaxed rhythm. Gather the family, hop in the car and arrive at your own private retreat. With our self-catering cottages you can enjoy all the Isle of Wight has to offer from your very own home-from-home. Read more
Travel solo, have a romantic getaway, or take advantage of some true family time and have a half-term to remember. Our self-catering cottages offer an idyllic retreat from the chaos of everyday life, so welcome in the summer and kick back. Many of our cottages are dog-friendly too, which means no one gets left behind this May half-term.
Self-Catering Cottages on the Isle of Wight this May Half-Term
Whether you're planning a much-anticipated holiday or are looking for a spontaneous last-minute break to spend your May half-term on the Isle of Wight, we will help you to find the holiday cottage of your dreams. At Classic Cottages, we pride ourselves on marketing only the finest quality holiday cottages on the Isle of Wight. Each of our cottages is handpicked; personally inspected and fully equipped to ensure your holiday is the best it can be. Every step of the way, we offer help and support so that your whole experience is as smooth and relaxed as possible.
If you have any questions, don't hesitate to get in touch.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 69 May half-term cottages on the Isle of Wight
7 nights from £1452
Merivale
42404 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...
7 nights from £1452
7 nights from £724
Grace Cottage
42091 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...
7 nights from £724
7 nights from £2300
Bayside House
41784 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight
This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes' walk to the water’s edge, a truly stunning holiday destination. The pro...
7 nights from £2300
7 nights from £1366
61 Solent View
40784 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight
On the outskirts of Seaview and within a few minutes' walk from Seagrove Bay, take in the stunning sea views from not one but two balconies. 61 Solent View is a wonderful holiday h...
7 nights from £1366
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.
7 nights from £1216
Keepers Cottage
40704 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...
7 nights from £1216
7 nights from £2862
Flackstead
39133 bedroom self catering cottage near the beach in Brook, Isle of Wight
Flackstead is a unique eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of co...
7 nights from £2862
7 nights from £597
Orchard Cottage
39362 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...
7 nights from £597
7 nights from £662
Blakes Barn
39072 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
If you are looking for a traditional cottage, look no further than Blakes Barn. Mattingly Farm is made up of three barns in total, Blakes Barn, Dairy Cottage (3912), and Orchard Co...
7 nights from £662
7 nights from £597
Dairy Cottage
39122 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...
7 nights from £597
Mattingley Farm
7 nights from £1855
