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 370 holiday cottages matching your search in the South West...

Little Blue is a 1 bedroom, dog friendly cottage near the sea near Falmouth, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £419

Little Blue

5864

1 bedroom, dog friendly cottage near the sea near Falmouth, Cornwall.


In the heart of the historic yet trendy town of Penryn and only a five minute drive to Falmouth is this perfect bolthole for two. Named one of the best towns to live in in the Sout...

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

7 nights from £419

The Yew Trees is a 2 bedroom dog friendly self catering cottage near Cheltenham.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1402

The Yew Trees

5862

2 bedroom dog friendly self catering cottage near Cheltenham.


This charming holiday cottage, nestled in the peaceful countryside just outside Cheltenham and the gorgeous Cotswolds, offers the perfect retreat for a tranquil getaway. Set in a r...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1402

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

View
  • 20% off

    2 May 2025 - 9 May 2025

    From £587.00 £469.60

Skapya Treehouse is a Luxury treehouse with hot tub in Gweek, Cornwall
  • Sleeps 2
  • No pets
  • Changeover Fri

From £200 per night

Skapya Treehouse

5858

Luxury treehouse with hot tub in Gweek, Cornwall


Surrounded by peaceful woodland in the charming Cornish hamlet of Gweek on the Lizard peninsula, Skapya is a beautifully crafted treehouse, hand-built from the finest cedar to blen...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £200 per night

Wisteria Cottage is a 3 bedroom holiday cottage with sea views in Falmouth, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1015

Wisteria Cottage

5860

3 bedroom holiday cottage with sea views in Falmouth, South Cornwall.


A beautiful Georgian cottage with a fabulous traditional Nordic hot tub with views over the sea. This really makes this property the perfect destination. Wisteria Cottage has be...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1015

View
  • 20% off

    2 May 2025 - 9 May 2025

    £1268.00 £1014.40

  • 20% off

    16 May 2025 - 22 May 2025

    From £1142.10 £913.68

March Hare is a 4 bedroom, dog friendly cottage near the beach in Cadgwith, Cornwall.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1006 *

March Hare

5852

4 bedroom, dog friendly cottage near the beach in Cadgwith, Cornwall.


Nestled in a prime location for exploring the south coast of Cornwall, this charming four bedroom bungalow is the perfect bolthole for families looking to relax and explore, arguab...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1006 *

Bridge Pool Cottage is a 3 bedroom, dog friendly cottage with sea views near Bodmin, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £784

Bridge Pool Cottage

5845

3 bedroom, dog friendly cottage with sea views near Bodmin, Cornwall.


In a picture-perfect setting, nestled on the banks of the River Camel in the pretty hamlet of Tresarrett, is this enchanting getaway, far from the rush of everyday, that promises r...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £784

Glebe Farmhouse is a 4 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £987

Glebe Farmhouse

5838

4 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.


Glebe Farmhouse is a delightful Grade II Listed, detached, granite cottage steeped in history and nestled in the rugged beauty of the Land's End peninsula. Tucked within a tranquil...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £987

View
  • 10% off

    2 May 2025 - 9 May 2025

    £987.00 £888.30

  • 10% off

    9 May 2025 - 16 May 2025

    £987.00 £888.30

  • 10% off

    23 May 2025 - 30 May 2025

    From £1226.00 £1103.40

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

The Barn is a 3 bedroom, dog friendly cottage near Praa Sands, South Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £807 *

The Barn

5847

3 bedroom, dog friendly cottage near Praa Sands, South Cornwall.


Situated in a great accessible location, yet close to sandy beaches and rugged coastal paths, this fabulous detached 'home-from-home' ticks all the holiday boxes. This welcoming th...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £807 *

The Pink Cottage is a 2 bedroom, dog friendly holiday cottage in Bude, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £544

The Pink Cottage

5835

2 bedroom, dog friendly holiday cottage in Bude, North Cornwall.


Nestled in the heart of Stratton, a village on the north Coast of Cornwall near Bude, you will discover The Pink Cottage, a beautiful holiday abode that's packed full of charm and ...

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

7 nights from £544

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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.