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 880 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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 880 cottages available for May half term

Kingfishers is a 1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £571

Kingfishers

6035

1 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.


Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Mon

7 nights from £571

The Gatehouse is a 2 bedroom self catering cottage in Malmesbury.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £840 *

The Gatehouse

6033

2 bedroom self catering cottage in Malmesbury.


If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £840 *

3 Kelly's Gardens is a 2 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £723 *

3 Kelly's Gardens

6056

2 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.


Tucked away in the very heart of St Ives, 3 Kelly's Gardens is a charming two bedroom terraced cottage and is the perfect spot for couples or families looking to soak up the town's...

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

7 nights from £723 *

Rockfield Lodge is a 3 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £957

Rockfield Lodge

6054

3 bedroom, dog friendly self catering cottage near Battle.


Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...

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

7 nights from £957

The Police House is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1572

The Police House

6051

4 bedroom, dog friendly holiday cottage near the beach in Seaview.


Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1572

Darling Chestnut is a 1 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £863

Darling Chestnut

6009

1 bedroom self catering cottage near Helford, West Cornwall.


Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £863

Starry Skies is a 2 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1342

Starry Skies

6008

2 bedroom self catering cottage near Helford, West Cornwall.


Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...

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

7 nights from £1342

Canonteign Cottage is a 4 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £3373

Canonteign Cottage

6018

4 bedroom, dog friendly cottage near Bovey Tracey, South Devon.


Introducing you to the fabulous Canonteign Cottage. Nestled in the idyllic grounds of Canonteign Falls and located in the renowned Dartmoor National Park, this wonderful family hol...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £3373

We are Gold accredited with the Green Tourism Business Scheme.

The Barn at Great Eckworthy is a 1 bedroom, dog friendly holiday cottage near Bideford, North Devon.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

The Barn at Great Eckworthy

6034

1 bedroom, dog friendly holiday cottage near Bideford, North Devon.


The Barn at Great Eckworthy is a stunning barn conversion, beautifully crafted and perfectly positioned in the rural hamlet of Buckland Brewer in the north Devon countryside yet on...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £185 per night

Hood's is a 2 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1488

Hood's

6045

2 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hoods provides luxur...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1488

Load 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.