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 33 handpicked cottages for May half term in Somerset

Florian is a Dog friendly converted shipping container with outdoor bath tub near Cheddar.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £706

Florian

5939

Dog friendly converted shipping container with outdoor bath tub near Cheddar.


This bijou beauty is just perfect for romantic getaways or for solo travellers seeking to escape the everyday. A stunning converted shipping container, it boasts idyllic countrysid...

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

7 nights from £706

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

7 nights from £780 *

The Smithy

5832

2 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...

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

7 nights from £780 *

Wheelwrights Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1561

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 £459 *

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 £459 *

View
  • 20% off

    20 Sep 2025 - 26 Sep 2025

    From £434.70 £347.76

  • 20% off

    26 Sep 2025 - 3 Oct 2025

    From £423.00 £338.40

  • 20% off

    3 Oct 2025 - 10 Oct 2025

    From £362.00 £289.60

  • 20% off

    10 Oct 2025 - 17 Oct 2025

    From £362.00 £289.60

  • 20% off

    17 Oct 2025 - 24 Oct 2025

    From £362.00 £289.60

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

7 nights from £592 *

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 £592 *

Merryfields is a 4 bedroom, dog friendly self catering cottage near Bath.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2031

Merryfields

5572

4 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 ...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2031

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 £808

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 Nati...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £808

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

7 nights from £517 *

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 £517 *

Our guests rate us 4.8/5 on Feefo, the independent review site.

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 £475

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 £475

Meadowbank is a 4 bedroom, dog friendly cottage with sea views in Porlock, Somerset.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1019 *

Meadowbank

5187

4 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...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1019 *

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.