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

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 1152 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. 

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

We have 1152 self catering cottages available to rent in May

The Studio is a 1 bedroom, dog friendly, cosy cottage near Ryde.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £440

The Studio

5753

1 bedroom, dog friendly, cosy cottage near Ryde.


Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...

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

7 nights from £440

The Old Dairy

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1278

Greenawell Farm Cottages

  • Sleeps 5 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £934

Horseshoe Cottage is a 2 bedroom self catering cottage near Moretonhampstead, Dartmoor.
  • Sleeps 3 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £486

Horseshoe Cottage

5747

2 bedroom self catering cottage near Moretonhampstead, Dartmoor.


Welcoming a true Dartmoor gem! This charming semi-detached stone cottage nestles neatly within the grounds of Greenawell Farm, boasting oodles of space, homely touches, and a fabul...

  • Sleeps 3 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £486

Greystones is a 5 bedroom dog friendly self catering cottage near the beach in Staithes.
  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £850

Greystones

5737

5 bedroom dog friendly self catering cottage near the beach in Staithes.


Welcome to Greystones, a fantastic holiday property for all the family, full of original features and perfectly located in the beautiful seaside village of Staithes in North Yorksh...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £850

No 12 is a 3 bedroom, dog friendly cottage with sea views in Ilfracombe, Devon.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £763 *

No 12

5738

3 bedroom, dog friendly cottage with sea views in Ilfracombe, Devon.


With views of Ilfracombe harbour framed by the gorgeous north Devon coastline, and where the sea meets the horizon, you've found not only a fabulous Victorian villa that has been s...

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

7 nights from £763 *

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

Bridge Cottage is a 4 bedroom, dog friendly cottage with sea views near Truro, Cornwall.
  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £965

Bridge Cottage

5751

4 bedroom, dog friendly cottage with sea views near Truro, Cornwall.


A charming and tranquil creekside cottage making the perfect escape, allowing one to wind down and appreciate the simpler things in life. Days can be enjoyed at a slower pace, in a...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £965

Sealark is a 2 bedroom, dog friendly holiday cottage near the beach near Whitby.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £630

Sealark

5626

2 bedroom, dog friendly holiday cottage near the beach near Whitby.


Close to the beautiful coastline, cliffs and sandy beaches of Runswick Bay, Staithes and Whitby sits this gem of a cottage sleeping four. Exuding a subtle and stylish coastal charm...

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

7 nights from £630

Kittiwake is a 2 bedroom apartment with sea views near Whitsand Bay, South Cornwall
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £895

Kittiwake

5754

2 bedroom apartment with sea views near Whitsand Bay, South Cornwall


With wonderful views of the sea and a mere hop, skip and jump to the beach, come and immerse yourself in the coastal way of life at this stunning retreat in the seaside hamlet of P...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £895

Gam Bridge Cottage is a 2 bedroom self catering cottage near Port Isaac, North Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £698

Gam Bridge Cottage

5639

2 bedroom self catering cottage near Port Isaac, North Cornwall.


Gam Bridge Cottage is an absolute gem! Set along a country lane in the heart of north Cornwall, it has been flawlessly renovated and impeccably styled to offer an extra special get...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £698

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