May half term holiday cottages

May half term holiday cottages

With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover a beautiful corner of the UK. Read more

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

We've got 516 holiday cottages matching your search in the South West...

Island Cottage is a 3 bedroom, dog friendly cottage set on the beach in Kingsand, Cornwall.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1260

Island Cottage

5960

3 bedroom, dog friendly cottage set on the beach in Kingsand, Cornwall.


Set right on the beach in the charming village of Kingsand, treat yourself to the ultimate seaside escape where the sound of the waves lapping on the seashore become your daily sou...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1260

The Milk Shed is a 2 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £667

The Milk Shed

5977

2 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.


Looking for a retreat that offers peace and tranquility in abundance, yet perfect for immersing yourself in north coast living - then look no further than The Milk Shed. Nestled in...

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

7 nights from £667

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Water's Edge is a 2 bedroom, dog friendly apartment with sea views in Looe, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £828

Water's Edge

5980

2 bedroom, dog friendly apartment with sea views in Looe, Cornwall.


With stunning estuary views over the waters of the Looe River to the countryside beyond and stylish interiors - Water's Edge is an absolute gem! Boasting a prime location, high abo...

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

7 nights from £828

The Works is a 2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £745

The Works

5970

2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.


Tucked away on a quiet road in the centre of vibrant Penzance, The Works is a unique reverse-level house which offers a stylish and welcoming base to explore the beauty and culture...

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

7 nights from £745

Ocean Break is a 2 bedroom holiday cottage near the beach in Croyde, North Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £890

Ocean Break

5965

2 bedroom holiday cottage near the beach in Croyde, North Devon.


Pack your bags and head to the glorious golden sands of Croyde beach with a stay at Ocean Break. This glorious north Devon seaside village is cradled by the surrounding hills. Afte...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £890

Devon Beach Court is a 3 bedroom, dog friendly apartment with sea views in Woolacombe.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1720

Devon Beach Court

5974

3 bedroom, dog friendly apartment with sea views in Woolacombe.


When the call of the sea can no longer be ignored it's time to head to the north Devon seaside town of Woolacombe with miles and miles of golden sand and endless opportunities to e...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1720

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  • 30% off

    11 Jul 2025 - 18 Jul 2025

    From £1701.00 £1190.70

Flat 3, 1 May Terrace is a 1 bedroom, dog friendly apartment near the beach near Sidmouth.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £574

Flat 3, 1 May Terrace

5953

1 bedroom, dog friendly apartment near the beach near Sidmouth.


Welcome to May Terrace and Regency Sidmouth. Just a few minutes' walk takes you to the beautiful seafront, promenade, beaches and magnificent red cliffs. En route you will discover...

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

7 nights from £574

Boak Villa is a 3 bedroom, dog friendly cottage with sea views in Coverack, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £735 *

Boak Villa

5969

3 bedroom, dog friendly cottage with sea views in Coverack, Cornwall.


Cradled into the hillside above the charming fishing village of Coverack, Boak Villa boasts a sunny disposition and offers some of the most spectacular sea views you'll find anywhe...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £735 *

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

The Mowhay is a 3 bedroom, dog friendly cottage with sea views in Padstow, Cornwall.
  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £924

The Mowhay

5945

3 bedroom, dog friendly cottage with sea views in Padstow, Cornwall.


Nestled in the rural hamlet of Crugmeer, surrounded by glorious countryside yet only a 15-minute walk to Cornwall’s dramatic north coast and a mile from Cornwall’s foodie hotspot o...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £924

Higher Pencobben is a 5 bedroom, dog friendly cottage near the beach near Hayle, Cornwall.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1082 *

Higher Pencobben

5950

5 bedroom, dog friendly cottage near the beach near Hayle, Cornwall.


Nestled in the heart of gently rolling countryside, protected by the National Trust, Higher Pencobben, accessed by a private lane, is a beautiful rural home offering a haven of pea...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1082 *

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With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to South West. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.