May Half Term Holiday Cottages

May Half Term Holiday Cottages

With a cool breeze and warm sunshine, May marks the start of summer and many happy times to come. Kick start your summer properly and hop in the car; a holiday in a luxury self-catering cottage awaits. Browse through our list of 806 available cottages and find your favourite. All of our cottages are handpicked; personally inspected and fully equipped so your holiday is the best it can be.Read more

Spend your days exploring deep, green countryside and skim stones across lazy streams. Follow the scent of salty air and head to the coast, spending long days on the beach flitting between soft sands and cool sea. Perch on a bench and watch as life goes by, before heading to a local restaurant to dine on fresh, local produce lovingly crafted and prepared by skilled hands. Then, when you've had your fill of exploring, turn your attention to relaxing. Throw yourself into the holiday spirit and land in your own private self-catering cottage, primed and ready for you. An early summer break in your own slice of paradise can give you the chance to unwind, catch up and settle into a slower, more considered rhythm.  

Spend your May-Half Term in a Luxury Retreat

Whether you are looking for a solo retreat or want to bring the whole family away for a much-needed break, May half term provides ample opportunity to escape to greener grass for a while. However you'd like to spend your time, our cottages offer wide variety and consistent quality. Many of our cottages are dog-friendly too, meaning everyone can join in this May half term. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 806 cottages available for May half term

Woodbine Barn is a 2 bedroom, dog friendly holiday cottage near Barnstaple, North Devon.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £922

Woodbine Barn

4080

2 bedroom, dog friendly holiday cottage near Barnstaple, North Devon.


Woodbine Barn is in a magical rural setting between the stunning beaches of the north Devon coast and the wilds of Exmoor National Park. This very high quality barn conversion is a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £922

Old Orchard Cabin is a Bespoke dog friendly cabin with hot tub in Colyton, Devon
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534

Old Orchard Cabin

3742

Bespoke dog friendly cabin with hot tub in Colyton, Devon


Snuggled into the hillside and reached on foot up through an ancient orchard, this bespoke cabin is the ultimate rural retreat. Gaze at the stars through the window from your super...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534

Shepherd's Rest is a Dog friendly shepherds hut near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

From £83 per night

Shepherd's Rest

4140

Dog friendly shepherds hut near Looe, South Cornwall.


If a shepherd could pick the perfect spot to take shelter and rest, then this wonderful bolthole for two, in the most glorious countryside setting, overlooking wildlife on the pond...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

From £83 per night

White Cottage is a 3 bedroom, rural cottage with sea views near Falmouth, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1059

White Cottage

4119

3 bedroom, rural cottage with sea views near Falmouth, West Cornwall.


White Cottage is a traditional Cornish cottage with fabulous views over the most beautiful part of the Helford River across to Frenchman's Creek, the rolling countryside and woods ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1059

Creek Cottage is a 3 bedroom, rural cottage with sea views near Falmouth, West Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £915

Creek Cottage

4120

3 bedroom, rural cottage with sea views near Falmouth, West Cornwall.


Hidden in the secluded hamlet of Lower Calamansack along narrow leafy Cornish lanes, Creek Cottage is discovered down a long private lane, with a stunning outlook across the pretti...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £915

Calamansack

  • Sleeps 10 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1974

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Ivy Cottage is a 2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £679

Ivy Cottage

4122

2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty (now ren...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £679

The Witch's Wagon at Warleggan is a Family size, dog friendly shepherds hut near Lostwithiel, South Cornwall with a hot tub
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £620 *

The Witch's Wagon at Warleggan

4090

Family size, dog friendly shepherds hut near Lostwithiel, South Cornwall with a hot tub


Fall under the spell of this stunning location with an unforgettable stay at the enchanting Witch's Wagon. Squirreled away in the pretty hamlet of Warleggan, yes it is a real place...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £620 *

Jays Cottage is a 2 bedroom, dog friendly holiday cottage near Modbury, South Devon.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £724

Jays Cottage

4117

2 bedroom, dog friendly holiday cottage near Modbury, South Devon.


Jays Cottage is a delightful friendly home-from-home situated in the 18th Century country estate of Colmer. The breathtaking locality of this cottage makes venturing out and about ...

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

7 nights from £724

The Old Manor House is a 5 bedroom, dog friendly cottage close to the beach near Lyme Regis.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2412

The Old Manor House

4124

5 bedroom, dog friendly cottage close to the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

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

7 nights from £2412

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