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 842 self catering cottages available to rent in May

Maybury is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1240

Maybury

5991

3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


Your dream coastal escape awaits in Seaview! Escape to elegant Maybury and stay in this beautifully styled home with sandy beaches and village amenities on your doorstep. This blis...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1240

Flipflops is a 3 bedroom, dog friendly cottage near the beach in Padstow, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £990

Flipflops

5981

3 bedroom, dog friendly cottage near the beach in Padstow, Cornwall.


Come and create cherished holiday memories at our coastal retreat, set in the little hamlet of Windmill, only half a mile from the beautiful sandy beach and rockpools of Trevone Ba...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £990

Our guests rate us 4.8/5 on Feefo, the independent review site.

Fenders is a 3 bedroom, dog friendly cottage near the beach in Totland.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1041

Fenders

5987

3 bedroom, dog friendly cottage near the beach in Totland.


Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1041

Dynnargh is a 5 bedroom, dog friendly cottage near Tavistock, North Cornwall.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1397 *

Dynnargh

5954

5 bedroom, dog friendly cottage near Tavistock, North Cornwall.


If you're looking for a house of dreams, tucked away in a Cornish hamlet surrounded by woodlands and lush green rolling hills, with that all important hot tub and outdoor terrace, ...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1397 *

Jolie Brise is a 3 bedroom, dog friendly cottage near the beach in Port Isaac.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £737 *

Jolie Brise

5875

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


Come and enjoy a coastal escape on the beautiful north Cornish coast, at this one-of-a-kind cottage. Tucked away along the wonderfully named 'Squeeze-ee-belly-alley', in the heart ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £737 *

The Barn at Little Windsor  is a 1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £479

The Barn at Little Windsor

5968

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


Nestled in the exceptionally pretty Looe valley, with wonderful views across the rolling countryside, come and immerse yourself in Cornish charm, rural bliss and a wonderful wildli...

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

7 nights from £479

Bluebell is a Dog-friendly showmans wagon with outdoor bath near Mawgan Porth, North Cornwall
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £583

Bluebell

5988

Dog-friendly showmans wagon with outdoor bath near Mawgan Porth, North Cornwall


We're super excited to introduce you to our very first showman's wagon, a stunningly romantic hideaway for two nestled in north Cornwall that's dog friendly too. Lovingly handcr...

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

7 nights from £583

Quay Cottage is a 2 bedroom, dog friendly cottage with sea views in Devoran, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £761

Quay Cottage

5975

2 bedroom, dog friendly cottage with sea views in Devoran, Cornwall.


With creekside views where you can watch the tide ebb and flow this cottage is the perfect escape. Tucked away in the heart of the charming creekside village of Devoran, this beaut...

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

7 nights from £761

We are Gold accredited with the Green Tourism Business Scheme.

Anderton Mill is a 2 bedroom, dog friendly cottage near Boscastle, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £685

Anderton Mill

5979

2 bedroom, dog friendly cottage near Boscastle, North Cornwall.


Looking for the ultimate 'escape away from it all' retreat, where peace and seclusion abound, then look no further than this enchanting woodland hideaway. Tucked away in the beauti...

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

7 nights from £685

Penberi is a 1 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £808

Penberi

5985

1 bedroom, dog friendly cottage with sea views near St Davids.


An idyllic getaway for two, a darling gem nestling in the magnificent Pembrokeshire coast within the National Park, surrounded by delightful landscaped gardens, panoramic sea views...

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

7 nights from £808

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 842 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.