May Half Term Holiday Cottages
With a cool breeze and warm sunshine, May marks the start of summer and many happy times to come. Kick start your summer properly and hop in the car; a holiday in a luxury self-catering cottage awaits. Browse through our list of 1029 available cottages and find your favourite. All of our cottages are handpicked; personally inspected and fully equipped so your holiday is the best it can be. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 1029 cottages available for May half term
7 nights from £1788 booking fees included
Langmoor House
61754 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.
Langmoor House is a luxury four bedroom property with commanding sea views and just a 30 second walk into Lyme Regis town. This exquisite and dog-friendly home is laid out over thr...
7 nights from £1788
7 nights from £678 booking fees included
Bloomsbury Cottage
61861 bedroom, dog friendly self catering cottage in Wadhurst.
For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...
7 nights from £678
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £1067 booking fees included
Broyle Cottage
61743 bedroom, dog friendly self catering cottage near Hailsham.
Tucked away in a peaceful hamlet near the village of Herstmonceux, this quintessential English country cottage lends itself to family gatherings, celebrations or romantic breaks. B...
7 nights from £1067
7 nights from £3732 booking fees included
Pen Den Har
61706 bedroom, dog friendly home with sea views in Kingsand, Cornwall.
Come and fall under the spell of this very special house, perfectly positioned in the heart of the utterly charming villages of Kingsand and Cawsand. Set in a plum elevated positio...
7 nights from £3732
British Travel Awards 2025
Best company for UK holiday home rentals
Ivy Cottage
216Charming Castletown cottage with large private garden
Set in the heart of historic Castletown, Ivy Cottage is a beautifully presented holiday home offering spacious accommodation, charming interiors and a surprisingly large private ga...
7 nights from £672 booking fees included
Ebony
6171Dog friendly cabin for two, with a wood-fired hot tub in Holsworthy, Devon.
Nestled in the heart of the Devonshire countryside, this beautifully crafted curved cabin offers the ultimate romantic retreat for two. Designed to blend comfort and nature, Eb...
7 nights from £672
7 nights from £1323 booking fees included
Marina View
61533 bedroom apartment with sea views in Falmouth, South Cornwall.
A stunning, elegant waterside apartment in the heart of the marina in Falmouth overlooking bobbing boats within a gated development. A wonderful location for exploring the town on ...
7 nights from £1323
7 nights from £590 booking fees included
Fisherman's View
61812 bedroom, dog friendly apartment with sea views in Saundersfoot.
For a seaside holiday, the beach doesn't get any closer than this! Step from the garden onto the sand. Fisherman's View is a superbly located ground floor apartment, sleeping up to...
7 nights from £590
7 nights from £1995 booking fees included
The Bowjy
61724 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
Come and create cherished holiday memories with family and friends at this stunning barn conversion. Tucked away along a quiet country lane, it is ideally located within easy reach...
7 nights from £1995
7 nights from £594 booking fees included
Juniper
6133Converted 1900s railway wagon with an outdoor bath in Wales.
Surrounded by the rolling landscapes of Wales, Juniper is a secluded hideaway where rustic charm meets modern comfort. Thoughtfully designed for slow living, it offers the perfect ...
7 nights from £594
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!
Spend your days exploring deep, green countryside and skim stones across lazy streams. Follow the scent of salty air and head to the coast, spending long days on the beach flitting between soft sands and cool sea. Perch on a bench and watch as life goes by, before heading to a local restaurant to dine on fresh, local produce lovingly crafted and prepared by skilled hands. Then, when you've had your fill of exploring, turn your attention to relaxing. Throw yourself into the holiday spirit and land in your own private self-catering cottage, primed and ready for you. An early summer break in your own slice of paradise can give you the chance to unwind, catch up and settle into a slower, more considered rhythm.
Spend your May-Half Term in a Luxury Retreat
Whether you are looking for a solo retreat or want to bring the whole family away for a much-needed break, May half term provides ample opportunity to escape to greener grass for a while. However you'd like to spend your time, our cottages offer wide variety and consistent quality. Many of our cottages are dog-friendly too, meaning everyone can join in this May half term.
