Somerset Cottages for May Day Bank Holiday
With the commitments of everyday life heavy from winter, May presents an excellent opportunity to escape for a while. And where better to spend your May Day bank holiday than Somerset? At Classic Cottages, we have a range of 37 self-catering holiday cottages available for you to choose from. Offering wide variety and consistent quality, you can look forward to a dream retreat in Somerset. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.37 cottages for a Somerset May Day bank holiday break
7 nights from £272 *
The Coach House
58162 bedroom, dog friendly holiday cottage near Wellington, Somerset.
Situated in the beautiful National Landscape of the Blackdown Hills, The Coach House is a spacious, characterful cottage ready to welcome you and your four-legged friend. As yo...
7 nights from £272 *
7 nights from £336 *
Cleveland Cottage
19682 bedroom cottage near the market town of Dulverton, Somerset.
Offering a 20% discount for parties of 2 (unless a special offer is already in place) this very pretty cottage, on the edge of Exmoor National Park, a few miles from the market tow...
7 nights from £336 *
7 nights from £350
Green Place
53131 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.
Wind your way through the historic streets of Wells to find Green Place nestling in a quiet mews offering a romantic getaway. With a vibrant and bustling high street, the city of W...
7 nights from £350
7 nights from £392 *
Pippins
53602 bedroom, dog friendly character cottage near Beaminster, Somerset.
Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...
7 nights from £392 *
7 nights from £428
Week Cottage
16361 bedroom, rural, dog friendly cottage near Dulverton, Somerset.
Sitting in the heart of Exmoor National Park, Week Cottage dates back to the 1690s and is all picture-book old world charm inside. A spacious boot-room, perfect for muddy boots (an...
7 nights from £428
7 nights from £431 *
Frogwell Cottage
47143 bedroom, dog friendly holiday cottage near Dulverton, Somerset.
Under the spectacle of Exmoor National Park International Dark Sky Reserve, picture yourself on holiday with a glass of bubbly in hand, surrounded by nothing but fields and country...
7 nights from £431 *
7 nights from £441 *
The Cowshed
47432 bedroom, dog friendly cottage near Lyme Regis, Dorset.
Nestled in the sleepy Somerset countryside, The Cowshed is a converted farm building, offering an excellent retreat. From the moment you arrive at this 'off the beaten track' setti...
7 nights from £441 *
7 nights from £444 *
Brookside Cottage
26382 bedroom thatched cottage near Nether Stowey, Somerset.
In a beautiful wooded valley in the east Quantock Hills National Landscape, Brookside Cottage is an idyllic getaway. This thatched semi-detached property lies within a conservat...
7 nights from £444 *
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20% off
17 Oct 2025 - 24 Oct 2025
From £589.00 £471.20
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 £466
Dieppy Farm Cottage
27881 bedroom, dog friendly holiday cottage near Dulverton, Somerset.
On the edge of Exmoor's stunning National Park - a designated International Dark Sky Reserve - Dieppy Farm Cottage is in the perfect spot for stargazing; on a cloudless night you w...
7 nights from £466
7 nights from £468 *
Minstrels
49302 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
As soon as you step through the front door of this gorgeous cottage, you will fall in love with its character and charm. It is easy to see where the cottage gets its name when you ...
7 nights from £468 *
Whether you are continuing a tradition and revisiting a firm favourite, or would like to try something different and find somewhere new, our Somerset collection offers ample opportunities to enjoy the county this May. From coastal cottages to country retreats to hubs in the middle of quaint towns, our properties cater for groups of all sizes. It's great news if you have a four-legged friend, as many are dog-friendly too. Browse through our 37 available self-catering cottages in Somerset and Exmoor and find the one to suit you. With each one carefully selected and fully equipped, you are sure to enjoy some of the finest accommodation in Somerset. Start May on the right foot and secure your May Day bank holiday break today. Everyone deserves to indulge in some TLC now and then, so why don't you?
