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 1180 self catering cottages available to rent in May
7 nights from £1084
Rosslyn
58004 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
Perfectly situated in the heart of the charming seaside village of St Mawes on the stunning Roseland peninsula, Rosslyn is a gorgeous traditional cottage, beautifully styled and ju...
7 nights from £1084
7 nights from £783
Strawberry Hole Barn
58142 bedroom thatched, dog friendly self catering cottage near Rye.
Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...
7 nights from £783
7 nights from £727
One Old School Cottages
58033 bedroom, dog friendly cottage near the beach in Portscatho.
Situated in the pretty hamlet of Gerrans, just a stroll away from the charming seaside village of Portscatho on the beautiful Roseland peninsula, One Old School Cottages is a charm...
7 nights from £727
7 nights from £604
Whipsiderry
58091 bedroom, dog friendly apartment near the beach in Newquay.
A fabulous top floor apartment with a great roof terrace with gorgeous views over the Gannel Estuary, rolling Cornish countryside and a snip of a sea view too. This bolthole for tw...
7 nights from £604
7 nights from £1200
The Old Farmhouse
57923 bedroom, dog friendly self catering cottage in Pickering.
Nestled on the edge of the North York Moors in the charming town of Pickering, this Grade II Listed terraced cottage effortlessly combines historic charm with contemporary luxury. ...
7 nights from £1200
7 nights from £494
Fell View
58123 bedroom, dog friendly self catering cottage near Hawes.
If you want to get away from it all, why not visit Fell View in Gunnerside! A cosy three bedroom cottage in the heart of the village with a local pub on your doorstep and a front c...
7 nights from £494
7 nights from £1020
Brooks Cottage
57443 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
Situated in the heart of St Mawes, you'll find the beautiful Brooks Cottage gazing out to sea. This welcoming three bedroom waterside getaway is the perfect place to unwind with yo...
7 nights from £1020
7 nights from £1184
Bryn Teifi
58073 bedroom self catering cottage near the beach near Abersoch.
At first glance, Bryn Teifi presents itself as a small traditional cottage with all its original features, yet behind the white-washed facade lies a bold, contemporary Scandinavian...
7 nights from £1184
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!
7 nights from £762
Glebe House
57432 bedroom, dog friendly cottage near the beach in St Mawes, Cornwall.
Tucked away in a quiet corner, just a stone's throw from the picturesque harbourside of St Mawes on the Roseland peninsula you will find Glebe House, a charming Cornish cottage, pe...
7 nights from £762
7 nights from £2135 *
La Casita
58064 bedroom self catering cottage in Porthleven, South Cornwall.
Discover your perfect countryside escape, nestled in the picturesque countryside, just a 20 minute stroll from the charming fishing village of Porthleven. This modern and luxurious...
7 nights from £2135 *
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 1180 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.
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