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

Kingfishers is a 1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £571

Kingfishers

6035

1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.


Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £571

The Gatehouse is a 2 bedroom self catering cottage in Malmesbury.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £840 *

The Gatehouse

6033

2 bedroom self catering cottage in Malmesbury.


If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £840 *

3 Kelly's Gardens is a 2 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £723 *

3 Kelly's Gardens

6056

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


Tucked away in the very heart of St Ives, 3 Kelly's Gardens is a charming two bedroom terraced cottage and is the perfect spot for couples or families looking to soak up the town's...

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

7 nights from £723 *

Darling Chestnut is a 1 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £863

Darling Chestnut

6009

1 bedroom self catering cottage near Helford, West Cornwall.


Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £863

Starry Skies is a 2 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1342

Starry Skies

6008

2 bedroom self catering cottage near Helford, West Cornwall.


Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1342

Canonteign Cottage is a 4 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £3373

Canonteign Cottage

6018

4 bedroom, dog friendly cottage near Bovey Tracey, South Devon.


Introducing you to the fabulous Canonteign Cottage. Nestled in the idyllic grounds of Canonteign Falls and located in the renowned Dartmoor National Park, this wonderful family hol...

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

7 nights from £3373

The Barn at Great Eckworthy is a 1 bedroom, dog friendly holiday cottage near Bideford, North Devon.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

The Barn at Great Eckworthy

6034

1 bedroom, dog friendly holiday cottage near Bideford, North Devon.


The Barn at Great Eckworthy is a stunning barn conversion, beautifully crafted and perfectly positioned in the rural hamlet of Buckland Brewer in the north Devon countryside yet on...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

Hood's is a 2 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1488

Hood's

6045

2 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hoods provides luxur...

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

7 nights from £1488

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Loaf is a 1 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £770

Loaf

6046

1 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £770

Hood's and Loaf at Kingsland Farm

  • Sleeps 6 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £2258

Load more

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.