May half term holiday cottages

May half term holiday cottages

With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover a beautiful corner of the UK. Read more

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

We've got 12 holiday cottages matching your search in North Yorkshire...

The Bothy is a 1 bedroom, dog friendly self catering cottage near Skipton.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £662 booking fees included

The Bothy

6125

1 bedroom, dog friendly self catering cottage near Skipton.


If you are craving a cosy getaway for two or a quiet friend's weekend, The Bothy is a great choice. It is a traditional, restored stone cottage sitting right in the heart of the de...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £662

No 9 is a 2 bedroom, dog friendly self catering cottage near York.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £826 booking fees included

No 9

6052

2 bedroom, dog friendly self catering cottage near York.


Tucked away in a quiet gated community only steps from the pretty centre of the market town of Helmsley, sits No 9, a pretty two-storey cottage surrounded by beech hedging and with...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £826

Number 5 is a 3 bedroom, dog friendly holiday cottage near the beach in Filey.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £818 booking fees included

Number 5

5868

3 bedroom, dog friendly holiday cottage near the beach in Filey.


This delightful holiday cottage in Filey offers a perfect blend of coastal charm and countryside accessibility as it's just a short stroll from the seaside but has easy access to t...

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

7 nights from £818

Yore View is a 2 bedroom, dog friendly self catering cottage near Hawes.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £712 booking fees included

Yore View

5958

2 bedroom, dog friendly self catering cottage near Hawes.


A warm welcome awaits at Yore View in the Yorkshire Dales, perched on a ridge with amazing views over the countryside and surrounded by a large garden, this thoughtful renovation h...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £712

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British Travel Awards 2025
Best company for UK holiday home rentals

Albie's Freight Train is a Dog friendly vintage railway carriage with a wood-fired hot tub near Richmond.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £89 per night + £53 booking fees

Albie's Freight Train

5967

Dog friendly vintage railway carriage with a wood-fired hot tub near Richmond.


All aboard this little beauty, a stunning converted train carriage complete with wood-fired hot tub. It's the perfect romantic, dog friendly getaway for two with gorgeous countrysi...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £89 per night

Fell View is a 3 bedroom, dog friendly self catering cottage near Hawes.
  • Sleeps 5
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £616 booking fees included

Fell View

5812

3 bedroom, dog friendly self catering cottage near Hawes.


If you want to get away from it all, why not visit Fell View in Gunnerside! A cosy three bedroom cottage in the heart of the village with a local pub on your doorstep and a front c...

  • Sleeps 5
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £616

School House is a 3 bedroom, dog friendly self catering cottage near the sea in Muston near Filey.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £852 booking fees included

School House

5704

3 bedroom, dog friendly self catering cottage near the sea in Muston near Filey.


This charming gem of a cottage is located in the pretty village of Muston, Yorkshire, which is listed in the Domesday Book. Close to the seaside town of Filey and one of England's ...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £852

Sealark is a 2 bedroom, dog friendly holiday cottage near the beach in Staithes.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £824 booking fees included

Sealark

5626

2 bedroom, dog friendly holiday cottage near the beach in Staithes.


Close to the beautiful coastline, cliffs and sandy beaches of Runswick Bay, Staithes and Whitby sits this gem of a cottage sleeping four. Exuding a subtle and stylish coastal charm...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £824

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 £829 booking fees included

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 £829

Sammi's Freight Train is a Dog friendly vintage railway carriage with wood-fired hot tub near Richmond.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £89 per night + £18 booking fees

Sammi's Freight Train

5287

Dog friendly vintage railway carriage with wood-fired hot tub near Richmond.


Immerse yourself in a restful rural getaway and escape the rush of everyday life. Disappear into the heart of the Yorkshire Dales and return for evening starlit soaks in the wood-f...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £89 per night

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With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to North Yorkshire. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.