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

Sandpiper is a 3 bedroom, dog friendly cottage with sea views in Shaldon, Devon.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1578

Sandpiper

4697

3 bedroom, dog friendly cottage with sea views in Shaldon, Devon.


This delightful house has marvellous views across the Teign estuary from the enclosed patio and garden, and from almost every room in the house. For those wanting to relax, thi...

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

7 nights from £1578

Walnut Barn is a 5 bedroom, dog friendly holiday cottage near Honiton, South Devon.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1302

Walnut Barn

4709

5 bedroom, dog friendly holiday cottage near Honiton, South Devon.


Welcome to Walnut Barn, a superbly renovated detached barn surrounded by magnificent countryside views which stretch for miles over the beautiful rolling Devon countryside. Soaking...

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

7 nights from £1302

Frogwell Cottage is a 3 bedroom, dog friendly holiday cottage near Dulverton, Somerset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £590 *

Frogwell Cottage

4714

3 bedroom, dog friendly holiday cottage near Dulverton, Somerset.


Under the spectacle of Exmoor National Park International Dark Sky Reserve, picture yourself on holiday with a glass of bubbly in hand, surrounded by nothing but fields and country...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £590 *

The Old Piggery is a 2 bedroom, dog friendly cottage near the beach near St Agnes.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £735

The Old Piggery

4749

2 bedroom, dog friendly cottage near the beach near St Agnes.


Nestled on the outskirts of the pretty Cornish seaside village of Porthtowan, up a windy track, this very special barn is the ideal 'get away from it all' destination. The Old Pigg...

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

7 nights from £735

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

Harbour View is a 4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2364

Harbour View

4731

4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.


Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2364

The Aval Loft is a 1 bedroom, dog friendly cottage near Tavistock, North Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £922

The Aval Loft

4706

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


Oh my goodness, The Aval Loft is simply gorgeous! Nestled in the heart of the countryside with the most lush and awe inspiring views stretching out across rolling pastures, ancient...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £922

La Cabine Francaise is a 1 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

From £87 per night

La Cabine Francaise

4726

1 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.


Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...

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

From £87 per night

Toby's Hut is a Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £95 per night

Toby's Hut

4723

Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.


Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...

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

From £95 per night

Belle Vue Cottage is a 3 bedroom, dog friendly self catering cottage in Totnes, South Devon.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £758

Belle Vue Cottage

4657

3 bedroom, dog friendly self catering cottage in Totnes, South Devon.


Nestled in the village of Rattery, only a short distance from Totnes and the glorious south Devon coast, this beautiful cottage is furnished with real charm and style. With an e...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £758

Chyvean is a 3 bedroom, dog friendly cottage near the beach near Porthleven.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £810 *

Chyvean

4724

3 bedroom, dog friendly cottage near the beach near Porthleven.


In the heart of a quintessential Cornish village and only 500 yards from the sea you will find the charming Chyvean. Nestled in Gunwalloe on the Lizard peninsula, this delightful s...

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

7 nights from £810 *

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

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