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 1301 self catering cottages available to rent in May

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

Mount Folly Penthouse is a 3 bedroom apartment with sea views near Kingsbridge, South Devon.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1417

Mount Folly Penthouse

6109

3 bedroom apartment with sea views near Kingsbridge, South Devon.


If you're looking for a beautifully finished penthouse apartment, boasting the most spectacular views from almost every window, a glorious hot tub and outdoor sauna perched overloo...

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

7 nights from £1417

Duxbury Lodge is a Dog-friendly elegant countryside lodge for two
  • Sleeps 2
  • Dogs welcome

Duxbury Lodge

201

Dog-friendly elegant countryside lodge for two


Duxbury Lodge is a contemporary barn conversion set alongside Duxbury Cottage, offering a stylish rural retreat for two in the south of the island. Thoughtfully designed and beauti...

  • Sleeps 2
  • Dogs welcome
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Dunks Cottage is a 4 bedroom, dog friendly self catering cottage near Cranbrook.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1287

Dunks Cottage

6074

4 bedroom, dog friendly self catering cottage near Cranbrook.


Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...

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

7 nights from £1287

Sea Breeze Cottage is a An idyllic coastal retreat for that unforgettable holiday.
  • Sleeps 4
  • No pets

Sea Breeze Cottage

200

An idyllic coastal retreat for that unforgettable holiday.


Sea Breeze Cottage is an idyllic coastal retreat for that unforgettable holiday. In the heart of Old Laxey, a stone's throw from the beach, pub & two popular restaurants. Wit...

  • Sleeps 4
  • No pets
The Old Stables is a 2 bedroom self catering cottage near Bridlington.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £741

The Old Stables

6093

2 bedroom self catering cottage near Bridlington.


Welcome to the Old Stables, a sanctuary of weathered red brick and rustic charm that captures the very soul of the Yorkshire Wolds. If you are looking for a getaway that swaps the ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £741

Little Chywoon Barn is a 2 bedroom cottage near Perranporth, North Cornwall
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £564 *

Little Chywoon Barn

6104

2 bedroom cottage near Perranporth, North Cornwall


Tucked away in peaceful countryside, this retreat is surrounded by verdant rural views and peaceful birdsong but is only 10 minutes from the golden sands of Perranporth. This charm...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £564 *

North Wing is a 2 bedroom apartment with sea views near Marazion, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £801 *

North Wing

6113

2 bedroom apartment with sea views near Marazion, West Cornwall.


Perched proudly above Mount's Bay, North Wing apartment forms part of the historic Acton Castle, an iconic landmark built in 1775 and listed with Historic England. Constructed from...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £801 *

The Ballacloan is a Ground floor apartment conveniently located on the promenade in Douglas
  • Sleeps 4 + cot
  • No pets

The Ballacloan

193

Ground floor apartment conveniently located on the promenade in Douglas


A coastal haven in the heart of Douglas Promenade The Ballacloan is the perfect family apartment to enjoy the heart of the Isle of Man in all its glory. Set directly on the prom...

  • Sleeps 4 + cot
  • No pets

Choose from our exclusive collection at the best prices with real time availability.

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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 1301 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.