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

14 Regent Terrace is a 2 bedroom, dog friendly, lower ground floor apartment with sea views in Penzance.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £695 *

14 Regent Terrace

6004

2 bedroom, dog friendly, lower ground floor apartment with sea views in Penzance.


Tucked away just behind the iconic promenade in Penzance and mere moments from the Jubilee Pool and the sparkling sea beyond, 14 Regent Terrace is a restored two bedroom traditiona...

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

7 nights from £695 *

The Granary is a 2 bedroom self catering cottage near Moretonhampstead, South Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £918

The Granary

6010

2 bedroom self catering cottage near Moretonhampstead, South Devon.


If it's a superb rural retreat you are looking for, look no further, The Granary at Greenawell Farm is the perfect package. The Granary is a beautiful stone cottage, finished to an...

  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £918

Greenawell Farm Cottages

  • Sleeps 9 + 4 cots in 3 properties
  • Changeover Fri

7 nights from £1921

The Little Woodland House is a Family size cabin with hot tub near Fowey, South Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £728 *

The Little Woodland House

6001

Family size cabin with hot tub near Fowey, South Cornwall.


Welcome to Little Woodland House, a peaceful yet full-of-life glamping retreat nestled in the picturesque Fowey Valley. This thoughtfully crafted wooden cabin is ideal for a romant...

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

7 nights from £728 *

Port and Starboard
 is a 4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1258

Port and Starboard

5982

4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.


In prime position overlooking St Mawes Bay with wonderful seascape views, beautiful interiors and gorgeous contemporary furnishings, semi-detached Port and Starboard is a fabulous ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1258

Hobbit Corner is a 1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £470

Hobbit Corner

5959

1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.


Wind your way along the leafy lanes to the peaceful hamlet of Trevelmond, in the heart of southeast Cornwall, where this little beauty is waiting to welcome you with open arms and ...

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

7 nights from £470

Roselands is a 4 bedroom, dog friendly cottage near the beach in Mullion, Cornwall.
  • Sleeps 8 + 3 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1488

Roselands

5989

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


A thoughtful and imaginative renovation has completely transformed this once humble bungalow into an spacious and elegant four-bedroom sanctuary, perfectly placed on Cornwall's rug...

  • Sleeps 8 + 3 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1488

View
  • 5% off

    4 Sep 2025 - 11 Sep 2025

    £1711.00 £1625.45

  • 5% off

    11 Sep 2025 - 18 Sep 2025

    From £1711.00 £1625.45

Brookfield is a 3 bedroom, dog friendly cottage near Callington, South Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1980 *

Brookfield

5999

3 bedroom, dog friendly cottage near Callington, South Cornwall.


Looking for a very special escape to the country, surrounded by open farmland, where peace and tranquility reign supreme, then look no further than Brookfield. Nestled on the edge ...

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

7 nights from £1980 *

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

Armsyde is a 4 bedroom, dog friendly cottage near the beach in Padstow, Cornwall.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1540

Armsyde

5978

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


Armsyde is the perfect holiday home for a group of family or friends who want to experience the ultimate slice of Padstow life. Situated in the old town, this gorgeous three-storey...

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

7 nights from £1540

Copper Bal Cottage is a 2 bedroom, dog friendly cottage near the beach near Marazion.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £556 *

Copper Bal Cottage

5998

2 bedroom, dog friendly cottage near the beach near Marazion.


Nestled in the picturesque Cornish village of Goldsithney, just moments from the coast and the hidden gem of Prussia Cove, Copper Bal Cottage is a delightful dog-friendly, two bedr...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £556 *

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.