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 805 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 805 cottages available for May half term

Wiggy's Cottage is a 3 bedroom, dog friendly cottage near the beach in St Mawes, Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £868

Wiggy's Cottage

5220

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


Situated in the vibrant heart of the much sought-after Roseland village of St Mawes, Wiggy's Cottage is a traditional Cornish cottage with oodles of character and perfectly positio...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £868

Jessie is a Luxury dog friendly Shepherds Hut near Battle.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £79 per night

Jessie

5231

Luxury dog friendly Shepherds Hut near Battle.


Jessie is a gorgeous shepherd's hut situated two hours from London, tucked away down a long meandering path in a paddock between crab apple and cherry trees, with views of the Suss...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £79 per night

South Barn at Pickeridge is a 3 bedroom, dog friendly self catering cottage near Haywards Heath.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1224

South Barn at Pickeridge

5211

3 bedroom, dog friendly self catering cottage near Haywards Heath.


South Barn at Pickeridge is tucked away on a 120 acre working farm in a secluded valley between West Hoathly and Ardingly. It's the perfect retreat for families and friends looking...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1224

The Fold is a 4 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2293

The Fold

5219

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


Choose The Fold for an unforgettable Pembrokeshire holiday. Let the photos speak a thousand words. Immersed in the enchanting, unspoilt beauty of North Pembrokeshire, very near Abe...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2293

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

Newclose Houseboat is a 4 bedroom houseboat with sea views in Bembridge, Isle of Wight
  • Sleeps 8
  • No pets
  • Changeover Sat

7 nights from £1791 *

Newclose Houseboat

5200

4 bedroom houseboat with sea views in Bembridge, Isle of Wight


Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...

  • Sleeps 8
  • No pets
  • Changeover Sat

7 nights from £1791 *

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

7 nights from £812

Chapel Cottage

5221

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


Chapel Cottage is a simply delightful traditional Cornish cottage situated in the corner of a row of similar properties in an elevated position overlooking beautiful St Mawes and F...

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

7 nights from £812

Bosun's Locker is a 1 bedroom apartment near the beach in St Mawes, South Cornwall.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £567

Bosun's Locker

5213

1 bedroom apartment near the beach in St Mawes, South Cornwall.


Welcome to Bosun's Locker, a hidden away apartment conveniently situated in the heart of the vibrant Roseland village of St Mawes and perfect for a car-free Cornish getaway for two...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £567

Meadowbank is a 4 bedroom, dog friendly cottage with sea views in Porlock, Somerset.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £999 *

Meadowbank

5187

4 bedroom, dog friendly cottage with sea views in Porlock, Somerset.


In the perfect situation on the edge of the rugged Exmoor National Park and on the stunning West Somerset coastline, Meadowbank is a stylish and beautiful home from which to explor...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £999 *

The Hillside Hut is a Dog-friendly shepherds hut near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

From £71 per night

The Hillside Hut

5199

Dog-friendly shepherds hut near Looe, South Cornwall.


Welcome to The Hillside Hut, an idyllic, peaceful retreat where you can immerse yourself in the very best that nature has to offer, surrounded by beautiful Cornish countryside and ...

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

From £71 per night

Polvellan Heights is a 2 bedroom apartment with sea views in Mousehole, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £1425

Polvellan Heights

5196

2 bedroom apartment with sea views in Mousehole, West Cornwall.


Tucked away in a prime cliffside position, with views that stretch out across the shimmering waters of Mousehole and as far as the eye can see along the west Cornish coast, Polvell...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £1425

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

Loading more