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 1320 self catering cottages available to rent in May

Wychbury is a 4 bedroom, dog friendly holiday cottage near Sidmouth, South Devon.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2645 booking fees included

Wychbury

6220

4 bedroom, dog friendly holiday cottage near Sidmouth, South Devon.


When it comes to the perfect house for that special family getaway with family or friends, Wychbury is the ideal choice. This beautiful house boasts an outdoor heated swimming pool...

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

7 nights from £2645

Elm Cottage is a 3 bedroom, dog friendly cottage near the sea near Minehead, Somerset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £801 * booking fees included

Elm Cottage

6212

3 bedroom, dog friendly cottage near the sea near Minehead, Somerset.


This gorgeous, dog-friendly three bedroom cottage is deceptively spacious with wonderful open plan living spaces and beautiful cottage gardens making it ideal for gatherings, famil...

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

7 nights from £801 *

Reserve your 2027 holiday for just £40.00

Find out more
Clapper Mill is a 4 bedroom, dog friendly cottage near the beach near Penzance.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1549 * booking fees included

Clapper Mill

6157

4 bedroom, dog friendly cottage near the beach near Penzance.


Tucked away in the peaceful hamlet of Lamorna, surrounded by lush countryside and enchanting gardens, Grade II Llisted Clapper Mill is a truly remarkable retreat where history meet...

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

7 nights from £1549 *

New Mill is a 2 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.
  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £877 booking fees included

New Mill

6191

2 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.


Welcome to this rather unique holiday retreat. New Mill is a rather deceiving name for this Grade II Listed watermill, which boasts many stunning original features, lovingly preser...

  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £877

British Travel Awards 2025 - Best Company For UK Holiday Home Rentals Logo

British Travel Awards 2025
Best company for UK holiday home rentals

Ballachrink Barn is a
  • Sleeps 4 + cot
  • Dogs welcome

Ballachrink Barn

222


Ballachrink Barn is a beautifully presented self-catering holiday cottage located in the peaceful village of Glen Maye on the west coast of the Isle of Man, just south of Peel. ...

  • Sleeps 4 + cot
  • Dogs welcome
Hillside View is a 3 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1005 booking fees included

Hillside View

6215

3 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.


Tucked away in the glorious Tamar Valley, Hillside View is a rather special holiday retreat where peace, beautiful countryside and the great outdoors are right on your doorstep. Wi...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1005

Box Cottage is a 3 bedroom, dog friendly cottage near the beach in Croyde, Devon.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £886 booking fees included

Box Cottage

6207

3 bedroom, dog friendly cottage near the beach in Croyde, Devon.


In the heart of the charming village of Georgeham, just two miles from the golden sands of Croyde Bay and one mile from beautiful Putsborough Beach, Box Cottage is perfectly placed...

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

7 nights from £886

Ruska is a Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £882 booking fees included

Ruska

6209

Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.


Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £882

Greystones at Ago's Leap is a Impressive Douglas home with private gardens and tennis court
  • Sleeps 6 + 2 cots
  • Dogs welcome

Greystones at Ago's Leap

221

Impressive Douglas home with private gardens and tennis court


Set along Quarterbridge Road in Douglas, Greystones is a striking and spacious home offering an impressive place to stay within easy reach of the Island's capital. Beautifully p...

  • Sleeps 6 + 2 cots
  • Dogs welcome
Goaf Cottage is a 2 bedroom, dog friendly self catering cottage near Whitby.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £836 booking fees included

Goaf Cottage

6204

2 bedroom, dog friendly self catering cottage near Whitby.


In a county of hills, dales and sandy beaches, you will find the moors village of Glaisdale and nestled in a sleepy lane sits Goaf Cottage, an old farm building converted into a go...

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

7 nights from £836

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

Load 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 1320 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.