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 1214 self catering cottages available to rent in May
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
Norfolk Place
209Homestay registered property - only available for bookings during TT & MGP periods
This beautiful property is registered with Homestay IOM Limited and is marketed exclusively through Island Escapes. Norfolk Place is available for self-catering accommodation durin...
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
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £670
Mr Brightside
61223 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
This semi-detached townhouse is perfectly placed to enjoy a traditional Norfolk seaside holiday; create special memories with loved ones in this well thought-out holiday home which...
7 nights from £670
7 nights from £478
Number 67
61311 bedroom, dog friendly apartment near the beach near Falmouth.
A beautifully stylish abode offering the ultimate retreat; just a 10 minute walk into Falmouth town centre or to the beach, this gorgeous ground floor apartment has been thoughtful...
7 nights from £478
7 nights from £1147
Dormy House
60843 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
Dormy House is single-storey beach house, nestled in an idyllic spot, just moments away from the stunning beaches of this much-loved village, along the north west Norfolk coastline...
7 nights from £1147
7 nights from £404
The Bothy
61251 bedroom, dog friendly self catering cottage near Skipton.
If you are craving a cosy getaway for two or a quiet friend's weekend, The Bothy is a great choice. It is a traditional, restored stone cottage sitting right in the heart of the de...
7 nights from £404
7 nights from £1120 *
12 Castle Street
61304 bedroom, dog friendly self catering cottage near Ruthin.
Step into a world of timeless elegance and sheer comfort in 12 Castle Street, where classic charm meets modern luxury and pure relaxation. Escape to this superbly renovated Victori...
7 nights from £1120 *
7 nights from £961 *
Mount View Cottage
61283 bedroom, dog friendly cottage with sea views in Marazion, Cornwall.
Tucked away along a narrow Cornish lane in the heart of Marazion, Mount View Cottage is a delightful coastal retreat with sweeping views across Mount's Bay towards the iconic St Mi...
7 nights from £961 *
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
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 1214 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.
