May Cottages Available in Somerset
The sun is shining, beaches are quiet, the countryside is blossoming and all around local events and festivals are starting to take place. For a getaway in Somerset, May provides the perfect holiday experience. Get out and about as much as you like and relax in equal doses. After all, you're on holiday. Browse our portfolio of [available] cottages and take a step closer to something special this May. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 32 luxury cottages available in Somerset in May
7 nights from £769 * booking fees included
The Old Dairy
60822 bedroom, dog friendly self catering cottage near Taunton, Somerset.
The Old Dairy is a warm and cosy conversion set in the picturesque rolling hills of north Somerset. It offers spacious accommodation for up to four guests and will really strike a ...
7 nights from £769 *
-
25% off
3 Jul 2026 - 10 Jul 2026
From £1008.00 £819.00 booking fees included
Wheelwrights Cottages
7 nights from £1474 booking fees included
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £737 * booking fees included
The Smithy
58322 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
If a stunning conversion bursting with original features situated in a sleepy Somerset village sounds attractive then The Smithy is the place for you. Situated in close proximity t...
7 nights from £737 *
7 nights from £636 * booking fees included
Yew Tree Barn
57842 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
Situated in a peaceful corner of Somerset, with uninterrupted countryside views across the Levels, Yew Tree Barn is a high quality barn conversion with a contemporary feel. Perfect...
7 nights from £636 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £2024 booking fees included
Merryfields
55724 bedroom, dog friendly self catering cottage near Bath.
This spacious detached Victorian house is set on a two acre site in the rural village of Colerne, occupying a spectacular position over Box Valley with views of Salisbury Plain in ...
7 nights from £2024
7 nights from £823 booking fees included
The Cottage at Ford Barton
54672 bedroom cottage in the Blackdown Hills near Wellington, Somerset.
Within the pretty Somerset village of Churchinford, this tranquil cottage has been furnished with comfort in mind. There is so much to explore locally with the Blackdown Hills Nati...
7 nights from £823
7 nights from £1022 * booking fees included
Meadowbank
51874 bedroom, dog friendly cottage with sea views in Porlock, Somerset.
In the perfect situation on the edge of the rugged Exmoor National Park and on the stunning West Somerset coastline, Meadowbank is a stylish and beautiful home from which to explor...
7 nights from £1022 *
7 nights from £797 * booking fees included
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 £797 *
-
25% off
10 Jul 2026 - 17 Jul 2026
From £832.50 £687.38 booking fees included
Wreath Farm
7 nights from £2605 booking fees included
From £76 per night + £53 booking fees
The Crook
5003Shepherds hut with wood-fired hot tub near Ilminster, Somerset.
Perfectly positioned in a peaceful spot, you will find this stunning shepherd's hut that has been masterfully created. The Crook is a true hideaway in glorious surroundings and you...
From £76 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.
Whether you're looking to embrace half-term with the children and do something special, want to secure yourself a private cottage with a hot tub for a romantic retreat, or stay in a dog-friendly holiday cottage for some fun adventures ahead of the summer crowds, make the most of our Somerset offerings in May. From one-bed boltholes to big family-friendly properties with room enough for all your nearest and dearest, you are sure to find the right space and place amongst our luxury collection.
Last-minute short break or well-deserved holiday planned in advance, treat yourself to a little luxury this May. With spring well underway and the county experiencing joyous post-winter rejuvenation, this is an excellent time to come to Somerset and give yourself a hard-earned rest in your own slice of heaven.
Classic Cottages for May in Somerset
From country to coast, wherever you feel most at home we will be able to provide you with luxury self-catering accommodation. Spectacular views, private swimming pool, sizzling barbecue, great local amenities and many, many more choices, we can help you tailor your retreat to be the best it can be. With all of our properties handpicked and personally inspected, we make sure only the finest quality cottages are on our books. Scout out your favourite and get ready to make memories to last a lifetime.
