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 1006 self catering cottages available to rent in May

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)
Moaney Quill Lodge is a Elegant countryside retreat in Laxey with beautiful gardens
  • Sleeps 7 + 2 cots
  • No pets

Moaney Quill Lodge

215

Elegant countryside retreat in Laxey with beautiful gardens


Tucked away in the heart of picturesque Laxey, Moaney Quill Lodge is a truly exceptional escape, blending timeless character with luxurious comfort to create a stay that feels both...

  • Sleeps 7 + 2 cots
  • No pets
Bay View House is a Large town house in Port Erin with view of Bradda head
  • Sleeps 12 + cot
  • Dogs welcome

Bay View House

214

Large town house in Port Erin with view of Bradda head


Bay View is a beautifully renovated six-bedroom townhouse in the heart of Port Erin, offering stylish and spacious accommodation for large families, groups of friends, and multi-ge...

  • Sleeps 12 + cot
  • Dogs welcome
The Sandy Den is a 1 bedroom, dog friendly apartment with sea views in Shaldon, Devon.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £554

The Sandy Den

6156

1 bedroom, dog friendly apartment with sea views in Shaldon, Devon.


Introducing The Sandy Den, a fabulous ground floor retreat for two within a converted Victorian residence located in the heart of the village of Shaldon in Teignmouth. This fabulou...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £554

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British Travel Awards 2025
Best company for UK holiday home rentals

Coniston is a
  • Sleeps 4
  • No pets

Coniston

213


Nestled on sought-after Scarlett Road in Castletown, this beautifully presented bungalow enjoys stunning sea views and offers a peaceful coastal retreat ideal for those seeking com...

  • Sleeps 4
  • No pets
Calf View is a Tranquil Cregneash cottage overlooking the Calf of Man
  • Sleeps 5 + cot
  • Dogs welcome

Calf View

206

Tranquil Cregneash cottage overlooking the Calf of Man


Perched above the timeless village of Cregneash, Calf View is a serene cottage with views framed by sweeping Manx vistas stretching towards shimmering seas and the wild beauty of t...

  • Sleeps 5 + cot
  • Dogs welcome
Bramley Lodge is a 1 bedroom self catering cottage near Heathfield.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Bramley Lodge

6137

1 bedroom self catering cottage near Heathfield.


Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Fenella Cottage is a Stylish coastal cottage in Peel, moments from the sandy beach
  • Sleeps 5 + 2 cots
  • No pets

Fenella Cottage

212

Stylish coastal cottage in Peel, moments from the sandy beach


This beautifully finished coastal cottage in the heart of Peel offers an effortless blend of contemporary comfort and genuine homely charm, just moments from the town's historic ha...

  • Sleeps 5 + 2 cots
  • No pets
Rheidiol Cottage is a 3 bedroom self catering cottage near the beach in St Davids.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £2000

Rheidiol Cottage

6149

3 bedroom self catering cottage near the beach in St Davids.


Let your next coastal adventure begin in splendid Rheidiol Cottage. Set in the heart of enchanting St Davids, on Wales' breathtaking Pembrokeshire coast, soak up the mystical vibe,...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £2000

The Woodlands is a 3 bedroom, dog friendly self catering cottage near Great Malvern.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £957 *

The Woodlands

6135

3 bedroom, dog friendly self catering cottage near Great Malvern.


A traditional bolthole with contemporary flair is just what you will find at The Woodlands. Cosseted in over two acres of gardens, this is a luxury retreat for families and friends...

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

7 nights from £957 *

We are Gold accredited with the Green Tourism Business Scheme.

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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 1006 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.