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 1306 self catering cottages available to rent in May
Round Table House
218A unique countryside retreat with breathtaking southern views
Round Table House stands high above the rolling countryside of Ronague, a remarkable retreat where contemporary style meets the character of a much-loved home. Its elevated positio...
From £108 per night + £53 booking fees
Bottle Lodge
6206Grade II Listed, lovingly restored 1807 Bottle Lodge for two in Staffordshire.
Sitting in the Staffordshire countryside at the entrance to Tixall Estate, a unique and historic stay awaits at Bottle Lodge - named for its quirky octagonal shape that looks like ...
From £108 per night
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £833 booking fees included
Beau's Barn
61973 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
Escape the everyday with a well-deserved break at this rural retreat, nestled in the glorious Cornish countryside, yet only four miles from Padstow, Cornwall's culinary capital, an...
7 nights from £833
7 nights from £672 booking fees included
Hawcombe Cottage
62051 bedroom, dog friendly cottage with sea views near Tavistock.
Tucked away in the pretty riverside village of Bere Ferrers, Hawcombe Cottage is a charming hideaway for two, perfectly placed for those seeking a peaceful escape surrounded by the...
7 nights from £672
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £687 booking fees included
April Cottage
61992 bedroom, dog friendly cottage near the beach near Coverack.
Tucked away in an historic beachside location, this chic yet characterful semi-detached cottage has been lovingly restored and brought back to life, creating the perfect escape for...
7 nights from £687
7 nights from £776 booking fees included
Little Owl Barn
61941 bedroom holiday cottage near the beach in Croyde, North Devon.
Tucked away in a secluded oasis, in the charming hamlet of Putsborough on north Devon's spectacular coastline, this beautifully renovated retreat is a hidden gem. Just a short stro...
7 nights from £776
7 nights from £949 booking fees included
Camusasaig
61892 bedroom self catering cottage with loch views near Fort William.
Perched on the water’s edge, with uninterrupted views of Loch Linnhe in all its glory, sits Camusasaig a charming and perfectly located cottage for two with all the romance of a Sc...
7 nights from £949
7 nights from £679 booking fees included
Riverside Cottage
61632 bedroom, dog friendly cottage with sea views in Flushing, Cornwall.
Tucked away in the pretty, waterside village of Flushing, this lovely terraced property is perfectly located in a peaceful spot and just a short stroll downhill to the water, only ...
7 nights from £679
7 nights from £2342 * booking fees included
Trevaskis Farmhouse
61666 bedroom, dog friendly self catering home near Hayle, West Cornwall.
Set within 28 acres of beautiful Cornish countryside, Trevaskis Farmhouse offers a truly special stay in the heart of rural west Cornwall. Located within the grounds of the much-lo...
7 nights from £2342 *
7 nights from £2050 * booking fees included
Carn Marth Lodge
61984 bedroom self catering cottage near Portreath, North Cornwall.
From the moment you arrive at Carn Marth Lodge, it's clear this is somewhere rather special. Beautifully designed throughout with luxurious finishes, generous living spaces and exc...
7 nights from £2050 *
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 1306 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.
