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

Blakes Barn is a 2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £662

Blakes Barn

3907

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


If you are looking for a traditional cottage, look no further than Blakes Barn. Mattingly Farm is made up of three barns in total, Blakes Barn, Dairy Cottage (3912), and Orchard Co...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £662

Dairy Cottage is a 2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £597

Dairy Cottage

3912

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £597

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Mattingley Farm

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1855

Foxglove is a 2 bedroom self catering cottage near Kingsbridge, South Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £780

Foxglove

3855

2 bedroom self catering cottage near Kingsbridge, South Devon.


Foxglove is an exceptionally charming, stone-built cottage nestled within 21 acres of the fabulous Stancombe Manor grounds. This picturesque and tranquil setting doesn't just offer...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £780

Coombe Cottage is a 2 bedroom, rural holiday cottage near Launceston, North Cornwall.
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £548

Coombe Cottage

3858

2 bedroom, rural holiday cottage near Launceston, North Cornwall.


Tucked away along a country lane, in 23 acres of Cornish meadows, woodland and streams, Coombe Cottage is the perfect retreat for those who want to get away from it all and enjoy a...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £548

Little Tregerry is a 1 bedroom, rural holiday cottage near Launceston, North Cornwall.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £397

Little Tregerry

3859

1 bedroom, rural holiday cottage near Launceston, North Cornwall.


If you're looking for a peaceful break for two, you need look no further than Little Tregerry. Located down a country lane, in the heart of the Cornish countryside, with meadows, s...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £397

The Studio is a 2 bedroom, dog friendly cottage near the beach in Mousehole.
  • Sleeps 3 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £735

The Studio

3853

2 bedroom, dog friendly cottage near the beach in Mousehole.


Welcome to The Studio, a gorgeous holiday abode nestled in beautiful countryside yet close to the stunning beaches and breath-taking scenery of the far west of Cornwall. Former...

  • Sleeps 3 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £735

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £731

6 St Josephs

3846

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £731

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The Chocolate House is a 1 bedroom holiday cottage near the beach in Penzance, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £666

The Chocolate House

3794

1 bedroom holiday cottage near the beach in Penzance, West Cornwall.


A perfect retreat for a couple to relax, The Chocolate House is a beautifully renovated 18th Century cottage set in iconic Chapel Street in Penzance. Although located close to the ...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £666

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

7 nights from £620 *

The Lion's Den at Warleggan

3831

Family-size shepherds hut with hot tub and dog friendly near Lostwithiel, South Cornwall.


As you wind through the moorland lanes that lead to the pretty rural hamlet of Warleggan, you'll appreciate why the locals have twinned this special place with CS Lewis' fantasy wo...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £620 *

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