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

Riverside is a 2 bedroom, dog friendly cottage with sea views in Flushing, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £707 booking fees included

Riverside

6163

2 bedroom, dog friendly cottage with sea views in Flushing, Cornwall.


Tucked away in the pretty, waterside village of Flushing, this lovely terraced property is perfectly located in a peaceful spot and just a short stroll downhill to the water, only ...

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

7 nights from £707

Porto Cottage is a 1 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £763 booking fees included

Porto Cottage

6195

1 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.


This stylish hideaway with individual interiors is set in a peaceful location just a short walk from the heart of the trendy, yet historic, village of St Agnes. Porto Cottage is a ...

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

7 nights from £763

Choose from our exclusive collection at the best prices with real time availability.

Island Cottage is a 3 bedroom cottage with sea views in Bigbury-on-Sea, South Devon.
  • Sleeps 7 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1468 booking fees included

Island Cottage

6196

3 bedroom cottage with sea views in Bigbury-on-Sea, South Devon.


Welcome to Island Cottage, nestled in the sought-after village of Bigbury-on-Sea, its elevated location provides beautiful views of both Bigbury beach, Bantham beach and the iconic...

  • Sleeps 7 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1468

Paloma is a Converted horsebox with outdoor bath near Malmesbury.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £103 per night + £53 booking fees

Paloma

6187

Converted horsebox with outdoor bath near Malmesbury.


Set in serene countryside near the Cotswolds, Paloma, a beautifully converted vintage horsebox, invites you to truly switch off and enjoy a peaceful break. Leave the daily rout...

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

From £103 per night

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Best company for UK holiday home rentals

1 South Terrace is a 3 bedroom, dog friendly cottage with sea views in Penzance, Cornwall.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1460 booking fees included

1 South Terrace

6162

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


Wake up to the sound of the sea, breathe in the salty air and experience one of Penzance’s most enviable locations. Perfectly positioned overlooking the seafront and iconic promena...

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

7 nights from £1460

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  • 20% off

    14 Aug 2026 - 21 Aug 2026

    From £2406.00 £1937.40 booking fees included

Woonsmith is a 2 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857 * booking fees included

Woonsmith

6192

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


Escape to the peace and allure of the Cornish countryside at this beautifully renovated two bedroom cottage with its secluded, exclusive wild swimming lake just outside the pretty ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857 *

Admiral's Den is a 2 bedroom, dog friendly apartment near the beach in Penzance.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £740 * booking fees included

Admiral's Den

6169

2 bedroom, dog friendly apartment near the beach in Penzance.


Step into a piece of Cornish history at Admiral’s Den, a two-bedroom apartment occupying a wing of the magnificent Grade II Listed Georgian Nancealverne House. Set within 25 acres ...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £740 *

Nancealverne Estate

  • Sleeps 8 + 4 cots in 2 properties
  • Changeover Sat

7 nights from £1613.19 booking fees included

Apple Loft Cottage is a 2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £873 * booking fees included

Apple Loft Cottage

6168

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


Nestled within 25 acres of enchanting grounds of historic Nancealverne House, Apple Loft Cottage is a beautifully restored property offering a peaceful stay steeped in centuries of...

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

7 nights from £873 *

Primrose Cottage is a 2 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £853 * booking fees included

Primrose Cottage

6179

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


Primrose Cottage is the quintessential Dorset coastal property with its pretty village location and gorgeous, enclosed garden - it is packed with character. This semi-detached two ...

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

7 nights from £853 *

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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.