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

The Barn at Newton Creek is a 3 bedroom, dog friendly cottage with estuary views in Newton Ferrers.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1215

The Barn at Newton Creek

6055

3 bedroom, dog friendly cottage with estuary views in Newton Ferrers.


Escape to the spellbinding haven of The Barn at Newton Creek, a truly enchanting waterside retreat where time slows, hearts rest, and nature whispers its secrets. Set in an enviabl...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1215

Plain An Gwarry is a 4 bedroom, dog friendly cottage near Mevagissey, South Cornwall.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1053

Plain An Gwarry

6064

4 bedroom, dog friendly cottage near Mevagissey, South Cornwall.


Nestled in the heart of the glorious Cornish countryside on the outskirts of the pretty village of St Ewe, close to the fabulous beaches of Gorran Haven and Mevagissey, Plain An Gw...

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

7 nights from £1053

Rosmelin is a 3 bedroom, dog friendly cottage near Wadebridge, North Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1564

Rosmelin

6059

3 bedroom, dog friendly cottage near Wadebridge, North Cornwall.


Nestled in the heart of the Cornish countryside, Rosmelin is a truly stunning hideaway that invites you to wrap yourself in the lap of luxury and be embraced by the peace and calm ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1564

The Byre is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £788

The Byre

6066

1 bedroom self catering cottage near Taunton, Somerset.


Located in the picturesque Blackdown Hills near the Somerset and Devon border you will find The Byre. A one bedroom converted cowshed which combines original character with modern ...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £788

The Stables is a 1 bedroom self catering cottage near Taunton, Somerset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £788

The Stables

6065

1 bedroom self catering cottage near Taunton, Somerset.


Located in the famous Blackdown Hills near the Somerset and Devon border you will find The Stables. A luxurious one bedroom converted stable which combines original character with ...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £788

Higher Trennal Farm is a 4 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1482 *

Higher Trennal Farm

6023

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


Step back in time at Higher Trennal Farm, an historic Cornish home dating back to 1740. Once known as Trenwall, this characterful farmhouse has been lovingly rebuilt and restored o...

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

7 nights from £1482 *

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  • 25% off

    22 Dec 2025 - 29 Dec 2025

    From £2020.50 £1515.38

Soul Surfer is a 2 bedroom apartment with sea views in Newquay, North Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £837

Soul Surfer

6061

2 bedroom apartment with sea views in Newquay, North Cornwall.


The embodiment of the surfing spirit can be found at this stunning apartment, simply open the windows and hear the waves crashing on the shore on the iconic Fistral beach. Gaze out...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £837

Swallow Cottage is a 2 bedroom, dog friendly holiday cottage in Bideford, North Devon.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £701 *

Swallow Cottage

6039

2 bedroom, dog friendly holiday cottage in Bideford, North Devon.


*During the Christmas/New Year period, bookings are available for a minimum of 12 guests staying in a minimum of two cottages.* Perched above a central courtyard with views acro...

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

7 nights from £701 *

Our property managers are local experts who handpick perfect places to stay.

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 *

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.