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 1235 self catering cottages available to rent in May
7 nights from £3290
Canonteign Cottage
60184 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
Introducing you to the fabulous Canonteign Cottage. Nestled in the idyllic grounds of Canonteign Falls, located in the infamous Dartmoor National Park. This wonderful family holida...
7 nights from £3290
From £185 per night
The Barn at Great Eckworthy
60341 bedroom, dog friendly holiday cottage near Bideford, North Devon.
The Barn at Great Eckworthy is a stunning barn conversion, beautifully crafted and perfectly positioned in the rural hamlet of Buckland Brewer in the north Devon countryside yet on...
From £185 per night
7 nights from £1400
Hood's
60452 bedroom, dog friendly self catering cottage near Bridport, Dorset.
This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hoods provides luxur...
7 nights from £1400
7 nights from £770
Loaf
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...
7 nights from £770
Hood's and Loaf at Kingsland Farm
7 nights from £2170
7 nights from £1295
Bro Tref Cottage
60224 bedroom, dog friendly cottage near the sea near Mawgan Porth.
A charming, semi-detached cottage found in the pretty village of St Mawgan; just a couple of miles away from the sandy beaches of Mawgan Porth and Watergate Bay. With a village sho...
7 nights from £1295
From £87 per night
Hornbeam Hideaway
6028Tipi with wood-fired outdoor bath near Hereford.
Reconnect with nature and book a getaway to your very own Tipi, hand-made in the Sioux-style and tucked away in the rolling Herefordshire countryside. Hornbeam Hideaway has eve...
From £87 per night
Tara
171A spacious family home just a short walk from Laxey village.
New for 2026! Tara is a modern and spacious family home in an elevated position in Laxey, offering stunning views of the sea and surrounding hills. This stylish self-catering a...
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £615
Mayflower Cottage
60202 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
Steeped in charm and just moments from the water's edge, this historic pink-washed cottage offers a quintessential taste of coastal life in one of Cornwall's most picturesque corne...
7 nights from £615
7 nights from £732 *
10 Hamilton Close
60303 bedroom, dog friendly holiday cottage in Hayle, West Cornwall.
Escape to the Cornish coast with a stay at 10 Hamilton Close, a beautifully presented three bedroomed detached home tucked away in the heart of Hayle. Perfect for families and frie...
7 nights from £732 *
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 1235 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.
