Holiday Cottages for May
May, that wonderful bridge between spring and summer, where temperatures begin to rise and blue skies and sunshine become a regular feature. Settle into the holiday mode and make the most of a quieter towns, beaches and countryside before summer crowds arrive. With new life and colour bursting at the scenes, this is a magical time of year, perfect for a holiday to refresh the senses and revive the soul. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 1178 self catering cottages available to rent in May
7 nights from £703
Bess 'n' Blue
61052 bedroom self catering cottage near the beach in Hunstanton.
Step inside this charming Victorian, terraced, holiday home, thoughtfully refurbished for relaxed family holidays and located just a few minutes' walk to the beaches of the gloriou...
7 nights from £703
Thie Vunn
207A blue-hued delight in the heart of Peel
Thie Vunn was lovingly gifted to Manx Wildlife Trust who are working with Island Escapes to welcome explorers eager to soak up every magical Manx moment. Spot this charming blue ho...
7 nights from £796
Northleigh Barn
61472 bedroom, dog friendly holiday cottage near Crediton, North Devon.
Welcome to Northleigh Barn, a splendid rural retreat, located on the Two Moors Way, providing the perfect setting for those wishing to relax and unwind in the most serene countrysi...
7 nights from £796
7 nights from £2391
The Old Dairy
61435 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
Gather family and friends to create cherished holiday memories at The Old Dairy, our delightful holiday cottage for up to 10 guests set on the beautiful Rame peninsula, Cornwall's ...
7 nights from £2391
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Wringford Cottages
7 nights from £4592
7 nights from £501
Bramble Cottage
61391 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
This delightful bolthole is the perfect escape for solo adventurers and couples looking for a charming, bijou retreat in one of Cornwall's most beautiful pockets. Set in the breath...
7 nights from £501
7 nights from £435
Azure Sky
6116Shepherds Hut with wood-fired hot tub and outdoor bath near Tintagel, Cornwall
Nestled within a 30-acre working farm in the scenic north Cornwall countryside, Azure Sky, an idyllic dog-friendly shepherd’s hut, is just the place for that peaceful escape you’ve...
7 nights from £435
7 nights from £645 *
Minnie's Cottage
61262 bedroom, dog friendly cottage near the beach near Bridport.
Minnie's Cottage is a cosy quintessential thatched cottage in the beautiful coastal village of Burton Bradstock. Situated in the heart of the village and just half a mile from the ...
7 nights from £645 *
7 nights from £529
Ketch
61142 bedroom, dog friendly apartment with sea views in Portscatho.
With far reaching views across Gerrans Bay and an easy stroll to the centre of the charming village of Portscatho on the Roseland peninsula, Ketch is a rather lovely first floor ap...
7 nights from £529
7 nights from £654
Shillings Cottage
61401 bedroom, dog friendly holiday cottage near Honiton, South Devon.
Sat on a gentle hillside, this pretty flint cottage with a glorious outdoor seasonal swimming pool and stunning gardens is perfect for those looking for peace and tranquility. Nest...
7 nights from £654
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If you've got children, May half-term provides an excellent opportunity to gather together the family and escape for a while on a dream holiday. Book yourself a luxury self-catering cottage and catch up properly - it's much easier without the distractions of everyday life. However many are in your gang, we'll help you find the perfect cottage. Many of our properties have a games room too, so the kids can keep themselves entertained. Or if your little ones are something of a water baby, why not book a holiday cottage with a swimming pool? We have shared and private pools to offer, so take your pick.
May isn't just about half term though. We also have two bank holidays to look forward to, as well as plenty of chances for spontaneous short breaks and much anticipated weeks away ahead of the summer. From idyllic one-bed retreats up to huge 8-bedroom properties big enough for all your nearest and dearest, you can tailor your dream holiday. It's good news for Fido too, as lots of our cottages are dog-friendly.
May Holidays
From country to coast, the holiday of a lifetime awaits you. Browse our list of 1178 available cottages and take a step closer to a luxury retreat in May. All of our cottages are handpicked; personally inspected and fully equipped with a complete inventory for your total ease and comfort.