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

Kingston Barns

  • Sleeps 11 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £2392

The Green House is a 2 bedroom, dog friendly cottage overlooking Nunney Brook near Frome, Somerset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £689

The Green House

4529

2 bedroom, dog friendly cottage overlooking Nunney Brook near Frome, Somerset.


Enjoy a glass of fizz overlooking the peaceful stream or curl up in the cosy sitting-room in front of the fire, whichever takes your fancy, this gorgeous retreat will deliver! This...

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

7 nights from £689

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Willow Cottage is a 1 bedroom, dog friendly holiday cottage near Falmouth, West Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £554

Willow Cottage

4516

1 bedroom, dog friendly holiday cottage near Falmouth, West Cornwall.


This idyllic hideaway is set in a tranquil country location, nestled in the owners' smallholding, in the romantic Helford area. Willow Cottage is a beautiful retreat for two (and y...

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

7 nights from £554

Homesdale is a 1 bedroom holiday apartment near the beach in Shaldon, South Devon.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £558

Homesdale

4514

1 bedroom holiday apartment near the beach in Shaldon, South Devon.


In the heart of Shaldon village, found at the mouth of the Teign estuary, is Homesdale. This charming apartment is the perfect hideaway, just right for a couple wanting to enjoy th...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £558

Little Bambaroo is a 1 bedroom cottage near the beach near Marazion, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £515

Little Bambaroo

4511

1 bedroom cottage near the beach near Marazion, West Cornwall.


What a little cutie! Picture-perfect and utterly charming, this delightful bolthole for two is set deep in the heart of the quaint Cornish village of Churchtown Gulval. Spot the 12...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £515

Station A is a Luxury 2 bedroom self catering cottage with sea views and wood burner near Fishguard.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £1276 *

Station A

4481

Luxury 2 bedroom self catering cottage with sea views and wood burner near Fishguard.


Standing magnificently and secluded on the rugged Pembrokeshire coast path, Station A is a unique structure that blends seamlessly into the rolling landscape and has fabulous panor...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £1276 *

View
  • 10% off

    6 Dec 2024 - 13 Dec 2024

    From £1168.00 £1051.20

Old Sandpitts Cottage is a 2 bedroom thatched cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £618

Old Sandpitts Cottage

4504

2 bedroom thatched cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £618

The Old Mill is a 2 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1089

The Old Mill

4503

2 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.


If you are looking for a beautifully unique and special property for a perfect Dorset holiday, then look no further than The Old Mill. Formerly a working mill, this gorgeous proper...

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

7 nights from £1089

Samphire is a 1 bedroom cottage near the beach in Portscatho, South Cornwall.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £941

Samphire

4487

1 bedroom cottage near the beach in Portscatho, South Cornwall.


Higher Rosevine Farm is an attractive collection of luxury barns that are situated around a central courtyard planted with olive trees and large Mediterranean pots giving a relaxed...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £941

View
  • 15% off

    20 Dec 2024 - 27 Dec 2024

    £1256.00 £1067.60

The Tea Hut is a 1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

From £81 per night

The Tea Hut

4477

1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.


The Tea Hut is situated up a private drive in High Hurstwood. Nestled in the picturesque Sussex countryside it is a great base from which to explore Ashdown Forest and the local to...

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

From £81 per night

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