Holiday Cottages for May

Holiday Cottages for May

May, that wonderful bridge between spring and summer, where temperatures begin to rise and blue skies and sunshine become a regular feature. Settle into the holiday mode and make the most of a quieter towns, beaches and countryside before summer crowds arrive. With new life and colour bursting at the scenes, this is a magical time of year, perfect for a holiday to refresh the senses and revive the soul. Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 1269 self catering cottages available to rent in May

Surby Mount is a A delightful rural setting near Port Erin, ideal for families.
  • Sleeps 7 + 2 cots
  • Dogs welcome

Surby Mount

204

A delightful rural setting near Port Erin, ideal for families.


Surby Mount is a beautifully appointed countryside retreat tucked away in the peaceful Surby, just a few minutes from the coastal village of Port Erin. Surrounded by rolling farmla...

  • Sleeps 7 + 2 cots
  • Dogs welcome
Ocean View at 32 is a 2 bedroom, dog friendly apartment with sea views in Saundersfoot.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £613

Ocean View at 32

6129

2 bedroom, dog friendly apartment with sea views in Saundersfoot.


Wake up to the soothing sound of the sea in Ocean View at 32. You'll fall in love with the glorious Blue Flag beach and uninterrupted, far reaching sea views from this sweet little...

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

7 nights from £613

Little Field is a 3 bedroom, dog friendly holiday cottage near the beach near Ryde.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £896 *

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £896 *

Kipper Cottage is a Cosy Peel cottage by the sea, perfect for sunset evenings
  • Sleeps 3 + cot
  • No pets

Kipper Cottage

202

Cosy Peel cottage by the sea, perfect for sunset evenings


Kipper Cottage is a beautifully refurbished coastal hideaway in the heart of Peel, offering an indulgent blend of contemporary comfort and homely charm just moments from the town’s...

  • Sleeps 3 + cot
  • No pets
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Abbey at Trail Lodge is a Stylish studio apartment located in an idyllic national glen.
  • Sleeps 2
  • Dogs welcome

Abbey at Trail Lodge

174

Stylish studio apartment located in an idyllic national glen.


Abbey at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasalla...

  • Sleeps 2
  • Dogs welcome
Silverburn at Trail Lodge is a Stylish studio apartment located in an idyllic national glen.
  • Sleeps 2
  • Dogs welcome

Silverburn at Trail Lodge

170

Stylish studio apartment located in an idyllic national glen.


Silverburn at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Balla...

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

7 nights from £447

The Gallery

6127

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


A cosy, rural retreat for two and a small dog; nestled in the Cornish countryside but only a 10 minute drive to the stunning north coast and a short drive to the city of Truro. Set...

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

7 nights from £447

Rose End Cottage is a 3 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
  • Sleeps 5
  • Dogs welcome
  • Changeover Fri

7 nights from £746 *

Rose End Cottage

6073

3 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.


Treat yourself to a well deserved break at this gem of a cottage, nestled on the edge of the village of St Issey and perfectly placed for discovering the very best of north Cornwal...

  • Sleeps 5
  • Dogs welcome
  • Changeover Fri

7 nights from £746 *

Y Beudy is a 4 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £913

Y Beudy

6107

4 bedroom, dog friendly cottage with sea views near St Davids.


With far reaching, uninterrupted, spectacular sea views, set in eight acres of countryside and expansive lawns, gorgeous, stone-built Y Beudy is a charming conversion of a traditio...

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

7 nights from £913

Ysgubor is a 2 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £600

Ysgubor

6106

2 bedroom, dog friendly cottage with sea views near St Davids.


Nestling in the magnificent glory of the dramatic, rugged Pembrokeshire coastline, offering golden beaches, crystal blue sea and pretty seaside villages, dog-friendly, Ysgubor (Gra...

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

7 nights from £600

Need more time? Reserve any cottage for up to 24 hours before booking.

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If you've got children, May half-term provides an excellent opportunity to gather together the family and escape for a while on a dream holiday. Book yourself a luxury self-catering cottage and catch up properly - it's much easier without the distractions of everyday life. However many are in your gang, we'll help you find the perfect cottage. Many of our properties have a games room too, so the kids can keep themselves entertained. Or if your little ones are something of a water baby, why not book a holiday cottage with a swimming pool? We have shared and private pools to offer, so take your pick.

May isn't just about half term though. We also have two bank holidays to look forward to, as well as plenty of chances for spontaneous short breaks and much anticipated weeks away ahead of the summer. From idyllic one-bed retreats up to huge 8-bedroom properties big enough for all your nearest and dearest, you can tailor your dream holiday. It's good news for Fido too, as lots of our cottages are dog-friendly.

May Holidays 

From country to coast, the holiday of a lifetime awaits you. Browse our list of 1269 available cottages and take a step closer to a luxury retreat in May. All of our cottages are handpicked; personally inspected and fully equipped with a complete inventory for your total ease and comfort.