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 1311 self catering cottages available to rent in May

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

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

From £230 per night + £53 booking fees

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

From £230 per night

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
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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

Ballacosney Cottage is a Stylish Laxey cottage with private gym and sauna
  • Sleeps 6 + cot
  • No pets

Ballacosney Cottage

219

Stylish Laxey cottage with private gym and sauna


Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...

  • Sleeps 6 + cot
  • No pets
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Rubena Cottage is a 2 bedroom, dog friendly cottage near the beach in Port Isaac.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £923 booking fees included

Rubena Cottage

6200

2 bedroom, dog friendly cottage near the beach in Port Isaac.


A mere hop, skip and a jump from the water's edge, this absolute gem of a cottage has been restored with exquisite care, creating a most desirable retreat that's perfect for warm s...

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

7 nights from £923

St Peter's House is a 2 bedroom self catering cottage in Gloucester.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £983 booking fees included

St Peter's House

6202

2 bedroom self catering cottage in Gloucester.


Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £983

Hooper's House is a 4 bedroom self catering cottage in Gloucester.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1241 booking fees included

Hooper's House

6203

4 bedroom self catering cottage in Gloucester.


Hooper's House is a centuries-old property sitting in harmony with the historic buildings of Gloucester Cathedral but with a contemporary interior vibe, mixing traditional and mode...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1241

Round Table House is a A unique countryside retreat with breathtaking southern views
  • Sleeps 8 + cot
  • Dogs welcome

Round Table House

218

A unique countryside retreat with breathtaking southern views


Round Table House stands high above the rolling countryside of Ronague, a remarkable retreat where contemporary style meets the character of a much-loved home. Its elevated positio...

  • Sleeps 8 + cot
  • Dogs welcome

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

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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 1311 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.