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 1271 self catering cottages available to rent in May

Apple Loft Cottage is a 2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £856 * booking fees included

Apple Loft Cottage

6168

2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.


Nestled within 25 acres of enchanting grounds of historic Nancealverne House, Apple Loft Cottage is a beautifully restored property offering a peaceful stay steeped in centuries of...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £856 *

Lavender Cottage is a 2 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £893 * booking fees included

Lavender Cottage

6176

2 bedroom, dog friendly cottage near the beach in Christchurch.


Lavender Cottage is a delightful two bedroom home with open plan living areas and wonderful outdoor space. Set in the exclusive Wick Village it is just a short walk from one of Dor...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £893 *

Need more time? Reserve any cottage for up to 24 hours before booking.

Primrose Cottage is a 2 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £800 * booking fees included

Primrose Cottage

6179

2 bedroom, dog friendly self catering cottage in Bridport, Dorset.


Primrose Cottage is the quintessential Dorset coastal property with its pretty village location and gorgeous, enclosed garden - it is packed with character. This semi-detached two ...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £800 *

View
  • 10% off

    17 Jul 2026 - 24 Jul 2026

    From £957.60 £924.84 booking fees included

  • 10% off

    24 Jul 2026 - 31 Jul 2026

    From £907.20 £879.48 booking fees included

Langmoor House is a 4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.
  • Sleeps 8 + 4 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1615 * booking fees included

Langmoor House

6175

4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.


Langmoor House is a luxury four bedroom property with commanding sea views and just a 30 second walk into Lyme Regis town. This exquisite and dog-friendly home is laid out over thr...

  • Sleeps 8 + 4 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1615 *

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Bloomsbury Cottage is a 1 bedroom, dog friendly self catering cottage in Wadhurst.
  • Sleeps 2 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £601 booking fees included

Bloomsbury Cottage

6186

1 bedroom, dog friendly self catering cottage in Wadhurst.


For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...

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

7 nights from £601

Broyle Cottage is a 3 bedroom, dog friendly self catering cottage near Hailsham.
  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £816 * booking fees included

Broyle Cottage

6174

3 bedroom, dog friendly self catering cottage near Hailsham.


Tucked away in a peaceful hamlet near the village of Herstmonceux, this quintessential English country cottage lends itself to family gatherings, celebrations or romantic breaks. B...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £816 *

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 £2867 * booking fees included

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 £2867 *

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)
The Old Carriage House is a 2 bedroom, dog friendly holiday cottage near Crediton, Devon.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £776 booking fees included

The Old Carriage House

6188

2 bedroom, dog friendly holiday cottage near Crediton, Devon.


  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £776

View
  • 15% off

    3 Jul 2026 - 10 Jul 2026

    £1088.00 £987.80 booking fees included

  • 15% off

    10 Jul 2026 - 17 Jul 2026

    From £1088.00 £987.80 booking fees included

  • 15% off

    17 Jul 2026 - 24 Jul 2026

    £1250.00 £1125.50 booking fees included

  • 15% off

    24 Jul 2026 - 31 Jul 2026

    £1250.00 £1125.50 booking fees included

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 £645 booking fees included

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 £645

View
  • 10% off

    2 Jul 2026 - 12 Jul 2026

    £874.00 £839.60 booking fees included

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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 1271 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.