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

The Old Dairy is a 2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £918

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £918

Wootton Lodge is a 4 bedroom, dog friendly cottage near South Molton, North Devon.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1184

Wootton Lodge

5550

4 bedroom, dog friendly cottage near South Molton, North Devon.


Discover Wootton Lodge nestled in a north Devon nook and set within 90 acres of woodland, meadows and streams - all waiting to be explored! Just a short drive away you will discove...

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

7 nights from £1184

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

Merryfields is a 4 bedroom, dog friendly self catering cottage near Bath.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2278

Merryfields

5572

4 bedroom, dog friendly self catering cottage near Bath.


This spacious detached Victorian house is set on a two acre site in the rural village of Colerne, occupying a spectacular position over Box Valley with views of Salisbury Plain in ...

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

7 nights from £2278

View
  • 20% off

    22 Nov 2024 - 29 Nov 2024

    £1645.00 £1316.00

Hillrise is a 4 bedroom, dog friendly self catering cottage near Whitby.
  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £770

Hillrise

5507

4 bedroom, dog friendly self catering cottage near Whitby.


Situated in the picturesque Yorkshire Moors village of Glaisdale, Hillrise is a delightful cottage to while away your holiday in. Lovingly restored with cosy interiors packed full ...

  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £770

River Garden Cottage is a 2 bedroom riverside cottage near Bakewell.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £808

River Garden Cottage

5503

2 bedroom riverside cottage near Bakewell.


Located in a small hamlet, Litton Mill, midway between Buxton and Bakewell, this utterly charming cottage is ideal for couples and young families seeking a getaway in the Derbyshir...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £808

Salty Blue is a 2 bedroom, dog friendly cottage near the beach in Appledore, Devon.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £677

Salty Blue

5534

2 bedroom, dog friendly cottage near the beach in Appledore, Devon.


Tucked away in the ye olde cobbled streets of Appledore, within a hop, skip and a jump of the picturesque quay, pubs and delis you will discover Salty Blue. A former fisherman's co...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £677

The Dolls House is a 1 bedroom, dog friendly cottage near the beach in Branscombe, Devon.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £822

The Dolls House

5527

1 bedroom, dog friendly cottage near the beach in Branscombe, Devon.


Welcome to the Dolls House. This super charming stone cottage makes the perfect abode for that special getaway. Set in the magical grounds of Trafalgar Barton Estate, nestled on a ...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £822

The Coach House is a 4 bedroom, dog friendly cottage near the beach in Branscombe, Devon.
  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1666

The Coach House

5528

4 bedroom, dog friendly cottage near the beach in Branscombe, Devon.


Set in the magical grounds of Trafalgar Barton Estate, nestled on a south-facing hillside, The Coach House has magical views over Branscombe Vale and out to the World Heritage Jura...

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

7 nights from £1666

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

Trafalgar Barton Estate

  • Sleeps 9 + 3 cots in 2 properties
  • Changeover Sat

7 nights from £2488

Cliff Cottage is a 5 bedroom self catering cottage near Lincoln.
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2102

Cliff Cottage

5479

5 bedroom self catering cottage near Lincoln.


Welcome to the wonderfully tranquil Cliff Cottage, situated in the Lincolnshire countryside on a working farm. Approached by a long private lane, this welcoming detached house offe...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £2102

Loading more