Somerset Retreats for May Half Term

Somerset Retreats for May Half Term

Make the most of longer daylight hours and quieter times ahead of the summer holidays; May half term is around the corner. Kick start your holiday and browse our list of available self-catering accommodation. We have a selection of luxury cottages of all shapes and sizes in Somerset primed and ready to welcome you.  Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 13 handpicked cottages for May half term in Somerset

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 £924 *

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 £924 *

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 £672 *

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 £672 *

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  • 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 £774

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 £774

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

From £96 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 £96 per night

Posy is a Shepherds hut with wood-fired outdoor bathtub near Ilminster, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £78 per night

Posy

4861

Shepherds hut with wood-fired outdoor bathtub near Ilminster, Somerset.


Nestled in a secluded spot, Posy is a gorgeous shepherd's hut where every last detail has been thought of. The natural, peaceful setting provides the perfect escape to the countrys...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £78 per night

Frogwell Cottage is a 3 bedroom, dog friendly holiday cottage near Dulverton, Somerset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £574 *

Frogwell Cottage

4714

3 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...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £574 *

The Piggery is a 2 bedroom rural barn conversion near Wells, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £751 *

The Piggery

4384

2 bedroom rural barn conversion near Wells, Somerset.


What a superb barn conversion! The Piggery is an exceptionally high quality detached property, newly converted and beautifully presented. Set on a working family farm, surrounded b...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £751 *

Headford Farm Cottage is a 1 bedroom rural cottage near Taunton, Somerset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Thu

7 nights from £549

Headford Farm Cottage

2809

1 bedroom rural cottage near Taunton, Somerset.


Headford Farm Cottage is on the edge of a rural hamlet, high up in Somerset's Quantock Hills National Landscape. This stunning ancient landscape covers 100 square kilometres of oak...

  • Sleeps 2 + cot
  • No pets
  • Changeover Thu

7 nights from £549

Choose from our exclusive collection at the best prices with real time availability.

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With the chaos of everyday life - school, jobs, housework - it's sometimes easy to let life fly by. Why not slow down the pace this May half term and book a self-catering cottage in Somerset? We have cottages of all shapes and sizes available, with cottages perfect for solo retreats to family-friendly homes big enough for all your nearest and dearest. Explore Somerset by day, making the most of its stunning countryside, impressive gorges, fine cuisine and striking towns. Then, when you've walked all you can walk, return to your private retreat and snuggle up. If you've got little ones in tow, many of our cottages even have games rooms, so the kids can keep themselves entertained in your home-from-home.

Somerset Self-Catering Cottages for May Half Term

At Classic Cottages we pride ourselves on marketing only the finest quality self-catering accommodation in Somerset and Exmoor. We personally inspect all of our properties, carefully handpicking them onto our books. Don't worry about packing everything and the kitchen sink either. Each property is also equipped with a full inventory, so that everything you could need and more is provided for you. From your bed linens to fluffy towels to enough crockery for everyone, we've got you covered. All that's left for you to do? Enjoy.