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

Clova Cottage is a 2 bedroom self catering cottage near Settle.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £639

Clova Cottage

5552

2 bedroom self catering cottage near Settle.


Nestled in the charming village of Long Preston with its village green and very own Maypole, semi-detached Clova Cottage is waiting to welcome you. The village is almost mid-way be...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £639

Clyst House Apartment is a 3 bedroom, dog friendly holiday apartment near Exeter, South Devon.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1160

Clyst House Apartment

5619

3 bedroom, dog friendly holiday apartment near Exeter, South Devon.


Perfectly situated in the village of Clyst Honiton, just a short journey away from the delights of the south Devon coast and surrounding verdant countryside, Clyst House Apartment ...

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

7 nights from £1160

Blue Mill Retreat is a 1 bedroom, dog friendly apartment near the beach in Fowey, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £676

Blue Mill Retreat

5600

1 bedroom, dog friendly apartment near the beach in Fowey, Cornwall.


For out-of-season breaks or lazy summer stays, come and immerse yourself in the Fowey way of life at the stylish Blue Mill Retreat. Fowey is a magical place, surrounded by beautifu...

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

7 nights from £676

2 West Nolands is a 4 bedroom, dog friendly home close to  Avebury.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1255

2 West Nolands

5603

4 bedroom, dog friendly home close to Avebury.


Within an hour of the beautiful city of Bath and if you tire of the local landscape, the south Cotswolds and the New Forest are close enough for a day trip. Your four-legged friend...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1255

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Bank Cottage is a 3 bedroom self catering cottage in Longborough.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1660

Bank Cottage

5606

3 bedroom self catering cottage in Longborough.


Nestled within the charming village of Longborough in the scenic north Cotswolds, this inviting three bedroom stone cottage embodies quintessential Cotswold charm. The picturesque ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1660

Owl's Rest is a Fabulous dog friendly Shepherds Hut with a outdoor bath near Coverack, South Cornwall.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £107 per night

Owl's Rest

5602

Fabulous dog friendly Shepherds Hut with a outdoor bath near Coverack, South Cornwall.


Hidden away in blissful countryside on the magical Lizard peninsula and within easy reach of the charming fishing villages of Coverack and Cadgwith, Owl's Rest is the sweetest shep...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £107 per night

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £928 *

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £928 *

Driftwood is a 2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £928 *

Driftwood

5613

2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do. Th...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £928 *

Colwell Bay Cottages

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

7 nights from £1856

4 Church Square is a 1 bedroom, dog friendly self catering cottage in Rye.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £553

4 Church Square

5520

1 bedroom, dog friendly self catering cottage in Rye.


Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...

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

7 nights from £553

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

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