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 1264 self catering cottages available to rent in May

Pen Den Har is a 6 bedroom, dog friendly home with sea views in Kingsand, Cornwall.
  • Sleeps 12 + 4 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2804 *

Pen Den Har

6170

6 bedroom, dog friendly home with sea views in Kingsand, Cornwall.


Come and fall under the spell of this very special house, perfectly positioned in the heart of the utterly charming villages of Kingsand and Cawsand. Set in a plum elevated positio...

  • Sleeps 12 + 4 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2804 *

Ivy Cottage is a Charming Castletown cottage with large private garden
  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)

Ivy Cottage

216

Charming Castletown cottage with large private garden


Set in the heart of historic Castletown, Ivy Cottage is a beautifully presented holiday home offering spacious accommodation, charming interiors and a surprisingly large private ga...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
Ebony is a Dog friendly cabin for two, with a wood-fired hot tub in Holsworthy, Devon.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £592

Ebony

6171

Dog friendly cabin for two, with a wood-fired hot tub in Holsworthy, Devon.


Nestled in the heart of the Devonshire countryside, this beautifully crafted curved cabin offers the ultimate romantic retreat for two. Designed to blend comfort and nature, Eb...

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

7 nights from £592

Marina View is a 3 bedroom apartment with sea views in Falmouth, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1204

Marina View

6153

3 bedroom apartment with sea views in Falmouth, South Cornwall.


A stunning, elegant waterside apartment in the heart of the marina in Falmouth overlooking bobbing boats within a gated development. A wonderful location for exploring the town on ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1204

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Best company for UK holiday home rentals

Fisherman's View is a 2 bedroom, dog friendly apartment with sea views in Saundersfoot.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £515

Fisherman's View

6181

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


For a seaside holiday, the beach doesn't get any closer than this! Step from the garden onto the sand. Fisherman's View is a superbly located ground floor apartment, sleeping up to...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £515

The Bowjy is a 4 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1846

The Bowjy

6172

4 bedroom, dog friendly holiday cottage near Looe, South Cornwall.


Come and create cherished holiday memories with family and friends at this stunning barn conversion. Tucked away along a quiet country lane, it is ideally located within easy reach...

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

7 nights from £1846

Juniper is a Converted 1900s railway wagon with an outdoor bath in Wales.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £517

Juniper

6133

Converted 1900s railway wagon with an outdoor bath in Wales.


Surrounded by the rolling landscapes of Wales, Juniper is a secluded hideaway where rustic charm meets modern comfort. Thoughtfully designed for slow living, it offers the perfect ...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £517

Seren is a Converted 1900s railway wagon with an outdoor bath in Wales.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £517

Seren

6134

Converted 1900s railway wagon with an outdoor bath in Wales.


Nestled amongst the rolling landscapes of Wales, Seren offers a peaceful escape for two. Surrounded by nature, this tranquil hideaway is designed for slowing down, unwinding, and r...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £517

View
  • 20% off

    10 Jul 2026 - 17 Jul 2026

    £763.00 £610.40

Larkspur Cottage is a 3 bedroom, dog friendly cottage near the beach in Praa Sands.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £885 *

Larkspur Cottage

6151

3 bedroom, dog friendly cottage near the beach in Praa Sands.


Located in the peaceful village of Germoe in west Cornwall, Larkspur Cottage is a picture-perfect thatched home brimming with history, charm and countryside tranquility. This encha...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £885 *

Bee's Cottage is a 2 bedroom, dog friendly cottage near the beach near Hunstanton.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £806

Bee's Cottage

6155

2 bedroom, dog friendly cottage near the beach near Hunstanton.


Escape to the stunning Norfolk coast and stay at Bee's Cottage that sits in the pretty village of Heacham. Sleeping up to four guests, this welcoming abode is perfect for couples, ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £806

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 1264 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.