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 14 handpicked cottages for May half term in Somerset

Orchard Barn is a 1 bedroom apartment with countryside views near Weston-super-Mare, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £608

Orchard Barn

5855

1 bedroom apartment with countryside views near Weston-super-Mare, Somerset.


Tucked away in an enviable position, looking out over paddocks and apple orchards you will find Orchard Barn, a stylish apartment for two lucky guests. As soon as you arrive at thi...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £608

The Coach House is a 2 bedroom, dog friendly holiday cottage near Wellington, Somerset.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £615

The Coach House

5816

2 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...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £615

The Cottage at Ford Barton is a 2 bedroom cottage in the Blackdown Hills near Wellington, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £785

The Cottage at Ford Barton

5467

2 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 (whi...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £785

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 £454

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 £454

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

From £97 per night

The Crook

5003

Shepherds 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...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £97 per night

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

From £97 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 £97 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 £734

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 £734

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

7 nights from £594 *

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 £594 *

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £569

Oak Tree Barn

3288

2 bedroom, dog friendly cottage near Taunton, Somerset.


Oak Tree Barn is a family-friendly barn conversion set within the beautiful foothills of the Quantock Hills National Landscape. It is perfectly placed in the peaceful setting of th...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £569

Lamb's Tale Shepherd's Hut is a Dog friendly shepherds hut with a hot tub, near Bridgwater in Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

From £94 per night

Lamb's Tale Shepherd's Hut

3246

Dog friendly shepherds hut with a hot tub, near Bridgwater in Somerset.


Somerset's Quantock Hills – a nine and a half thousand acre Area of Outstanding Natural Beauty – rise up just behind the farm setting for this beautifully crafted, bespoke Shepherd...

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

From £94 per night

Load more

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.