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

Captains Cottage is a 3 bedroom, dog friendly cottage with sea views in Brixham, Devon.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £744

Captains Cottage

5444

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


Captains Cottage sits in an enviable position just moments away from the bustling Brixham harbourside, perfectly placed for family holidays or groups of friends looking for a coast...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £744

View
  • 15% off

    22 Nov 2024 - 29 Nov 2024

    £624.00 £530.40

  • 15% off

    29 Nov 2024 - 6 Dec 2024

    £624.00 £530.40

  • 15% off

    6 Dec 2024 - 13 Dec 2024

    £624.00 £530.40

  • 15% off

    13 Dec 2024 - 20 Dec 2024

    From £624.00 £530.40

Freshfields is a 4 bedroom self catering cottage near Dorchester, Dorset.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1233

Freshfields

5706

4 bedroom self catering cottage near Dorchester, Dorset.


Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1233

Aurora at 24 Acres is a Shepherds Hut in Devon with outdoor bath and luxury interiors.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £120 per night

Aurora at 24 Acres

5736

Shepherds Hut in Devon with outdoor bath and luxury interiors.


Welcome to Aurora, a gorgeous shepherd's hut for two, hidden away in a secluded setting in the Blackdown Hills. Nestled within a peaceful meadow on a 24-acre site and surrounded by...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £120 per night

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1040

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1040

Briar Lea is a 2 bedroom, dog friendly cottage with sea views in Robin Hoods Bay.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £744

Briar Lea

5694

2 bedroom, dog friendly cottage with sea views in Robin Hoods Bay.


Nestled in the quiet coastal village of Fylingthorpe with views across the sea to the rugged Yorkshire coastline and within minutes of the historic Robin Hood's Bay, this beautiful...

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

7 nights from £744

Penfoye is a 3 bedroom, dog friendly cottage with sea views near Fowey, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2377

Penfoye

5728

3 bedroom, dog friendly cottage with sea views near Fowey, Cornwall.


If there was a definition of 'heaven on earth' then Penfoye would be it. With spellbinding waterside scenes, beautifully curated interiors and glorious gardens, this extra-special ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2377

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

Rivendell Cottage is a 2 bedroom, dog friendly cottage near Camelford, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £529

Rivendell Cottage

5732

2 bedroom, dog friendly cottage near Camelford, North Cornwall.


Wind your way along the country lanes to this picture-perfect cottage, nestled in the rural hamlet of Tremail in the heart of north Cornwall. Serving up the best of both worlds, th...

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

7 nights from £529

The Threshing Barn is a 3 bedroom, dog friendly holiday cottage near Okehampton, North Devon.
  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £600 *

The Threshing Barn

5733

3 bedroom, dog friendly holiday cottage near Okehampton, North Devon.


Nestled in a quaint west Devon village, escape to the tranquility of village life and a slower pace at The Threshing Barn. This newly fully refurbished barn offers style and charm ...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £600 *

View
  • 15% off

    22 Nov 2024 - 29 Nov 2024

    From £585.00 £497.25

  • 15% off

    6 Dec 2024 - 13 Dec 2024

    From £585.00 £497.25

  • 20% off

    13 Dec 2024 - 20 Dec 2024

    From £585.00 £468.00

  • 20% off

    27 Dec 2024 - 3 Jan 2025

    £1078.00 £862.40

The Hayloft is a 2 bedroom thatched, dog friendly cottage near Okehampton, Devon.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £650

The Hayloft

5734

2 bedroom thatched, dog friendly cottage near Okehampton, Devon.


Escape to rural Devon bliss and become an Exbourne village local for a week; from walking the numerous bridle paths to popping to the local pub for a swift half, not forgetting you...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £650

View
  • 15% off

    22 Nov 2024 - 29 Nov 2024

    £550.00 £467.50

  • 15% off

    29 Nov 2024 - 6 Dec 2024

    £550.00 £467.50

  • 15% off

    6 Dec 2024 - 13 Dec 2024

    £550.00 £467.50

  • 15% off

    13 Dec 2024 - 20 Dec 2024

    From £550.00 £467.50

  • 15% off

    20 Dec 2024 - 23 Dec 2024

    £546.00 £464.10

Koes Cabin is a Woodland eco cabin near the North Coast of Cornwall
  • Sleeps 6
  • No pets
  • Changeover Fri

From £350 per night

Koes Cabin

5720

Woodland eco cabin near the North Coast of Cornwall


If you're searching for a tranquil, off-grid escape close to the Cornish coastline, Koes Cabin is just the place. Koes, meaning woodland in Cornish, is nestled within a magical 43-...

  • Sleeps 6
  • No pets
  • Changeover Fri

From £350 per night

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