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 596 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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 596 cottages available for May half term

The Barn is a 3 bedroom, dog friendly cottage near Praa Sands, South Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £889 *

The Barn

5847

3 bedroom, dog friendly cottage near Praa Sands, South Cornwall.


Situated in a great accessible location, yet close to sandy beaches and rugged coastal paths, this fabulous 'home from home' ticks all the holiday boxes. This welcoming three bedro...

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

7 nights from £889 *

The Pink Cottage is a 2 bedroom, dog friendly holiday cottage in Bude, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £713

The Pink Cottage

5835

2 bedroom, dog friendly holiday cottage in Bude, North Cornwall.


Nestled in the heart of Stratton, a village on the north Coast of Cornwall near Bude, you will discover The Pink Cottage, a beautiful holiday abode that's packed full of charm and ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £713

Bodillys Cottage is a 2 bedroom, dog friendly cottage near the beach in Newlyn, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £868 *

Bodillys Cottage

5805

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


Nestled in a tucked away quiet lane amidst the vibrant harbour town of Newlyn, this charming, cosy terraced cottage offers a perfect retreat for up to four lucky guests. Lovingly u...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £868 *

The Lighthouse Keeper's Cabin is a Dog friendly lighthouse cabin, with sea views and hot tub near Cardiff, Wales.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Mon

From £195 per night

The Lighthouse Keeper's Cabin

5836

Dog friendly lighthouse cabin, with sea views and hot tub near Cardiff, Wales.


Set sail for the getaway of your dreams with a magical stay in a very special hideaway overlooking the ocean. The Lighthouse Keeper's Cabin is perfectly situated just a stone's thr...

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

From £195 per night

The Dell is a Dog friendly shepherds hut with a hot tub and wood-burner near Kingsbridge, South Devon.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

From £98 per night

The Dell

5841

Dog friendly shepherds hut with a hot tub and wood-burner near Kingsbridge, South Devon.


Nestled in the lush verdant countryside of rural south Devon, The Dell is a nature lover's delight and ideally situated just a short drive away from the stunning Devonshire coast a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

From £98 per night

Lodge Cottage is a 3 bedroom, dog friendly self catering cottage near Helmsley.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1044

Lodge Cottage

5834

3 bedroom, dog friendly self catering cottage near Helmsley.


Nestled in the beautiful Yorkshire countryside is Lodge Cottage, close to the popular market town of Helmsley, foodie town of Malton and Hovingham, a delightful village with a stre...

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

7 nights from £1044

Mellifount Farm is a 2 bedroom self catering cottage near Haywards Heath.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £741

Mellifount Farm

5839

2 bedroom self catering cottage near Haywards Heath.


Escape to the Sussex countryside and stay in this beautiful oak-framed barn situated in a quiet rural location overlooking wooded farmland and paddocks, where you can sometimes see...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £741

The Smithy is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £757

The Smithy

5832

2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.


If a stunning conversion bursting with original features situated in a sleepy Somerset village sounds attractive then The Smithy is the place for you. Situated in close proximity t...

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

7 nights from £757

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

Wheelwrights Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1514

Brea Barn Cottage is a 2 bedroom, dog friendly cottage with sea views near Penzance.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £872 *

Brea Barn Cottage

5837

2 bedroom, dog friendly cottage with sea views near Penzance.


Escape to this delightful 17th Century barn conversion set within a National Landscape (formerly known as an Area of Outstanding Natural Beauty). With exceptional sea views and stu...

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

7 nights from £872 *

View
  • 10% off

    14 Mar 2025 - 21 Mar 2025

    From £768.00 £691.20

  • 10% off

    21 Mar 2025 - 28 Mar 2025

    From £827.00 £744.30

Load 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.