May Cottages Available in Somerset

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 23 luxury cottages available in Somerset in May

The Cygnet - Lodge 11 is a 2 bedroom self catering cottage near Lyme Regis, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £862 *

The Cygnet - Lodge 11

6044

2 bedroom self catering cottage near Lyme Regis, Somerset.


Situated on the Cricket St Thomas estate and close to the borders of Somerset, Dorset and Devon, is The Cygnet - Lodge 11, a luxury Scandinavian style lodge. It is part of the sele...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £862 *

The Old Dairy is a 2 bedroom, dog friendly self catering cottage near Taunton, Somerset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £627 *

The Old Dairy

6082

2 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 ...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £627 *

View
  • 20% off

    15 May 2026 - 22 May 2026

    From £756.00 £604.80

  • 20% off

    5 Jun 2026 - 12 Jun 2026

    From £907.20 £725.76

The Byre is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £708

The Byre

6066

1 bedroom self catering cottage near Taunton, Somerset.


**The Byre can accommodate flexible check in days – please contact us to request.** Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find T...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £708

The Stables is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £637

The Stables

6065

1 bedroom self catering cottage near Taunton, Somerset.


**The Stables can accommodate flexible check in days – please contact us to request.** Located in the famous Blackdown Hills near the Somerset and Devon border you will find The...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £637

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Yew Tree Barn is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £573 *

Yew Tree Barn

5784

2 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...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £573 *

Pippins is a 2 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £510 *

Pippins

5360

2 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...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £510 *

Green Place is a 1 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £450

Green Place

5313

1 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...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £450

The Cowshed is a 2 bedroom, dog friendly cottage near Lyme Regis, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £632 *

The Cowshed

4743

2 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...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £632 *

View
  • 20% off

    15 May 2026 - 22 May 2026

    From £711.00 £568.80

The Whistle is a Shepherds hut with wood-fired hot tub near Ilminster, Somerset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £94 per night

The Whistle

5004

Shepherds hut with wood-fired hot tub near Ilminster, Somerset.


If you are looking for a luxurious and unique glamping experience, then look no further than The Whistle. A gorgeously designed shepherd's hut, complete with enchanting outside spa...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £94 per night

Minstrels is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £674 *

Minstrels

4930

2 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 ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £674 *

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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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.