Cottages For May in North Yorkshire

Cottages For May in North Yorkshire

Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit North Yorkshire Read more

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

We have 12 self catering cottages available to rent in May in North Yorkshire

Grove Villa is a 4 bedroom self catering cottage in Leyburn.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1650

Grove Villa

5833

4 bedroom self catering cottage in Leyburn.


If a stunning property with original features along with contemporary design in the heart of a Yorkshire Dales market town sounds attractive then Grove Villa is the place for you. ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1650

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

7 nights from £877

Lodge Cottage

5834

3 bedroom, dog friendly self catering cottage near Helmsley.


Nestled in the beautiful Yorkshire countryside is Lodge Cottage, close to the popular market town of Helmsley, foodie town of Malton and Hovingham, a delightful village with a stre...

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

7 nights from £877

Low Shaw Farmhouse is a 4 bedroom, dog friendly self catering cottage in Hawes.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £935 *

Low Shaw Farmhouse

5794

4 bedroom, dog friendly self catering cottage in Hawes.


As you approach the hamlet of Simonstone and look up to the hill on your right you will see Low Shaw Farmhouse nestled on the hillside, surrounded by sheep enclosed by the wonderfu...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £935 *

The Haven is a 2 bedroom self catering cottage near Hawes.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £570

The Haven

5778

2 bedroom self catering cottage near Hawes.


As its name implies, The Haven is a lovely stone cottage in the heart of the Yorkshire Dales in the quintessential country village of Gunnerside with its pretty bridge, picturesque...

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

7 nights from £570

Greystones is a 5 bedroom dog friendly self catering cottage near the beach in Staithes.
  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £383 *

Greystones

5737

5 bedroom dog friendly self catering cottage near the beach in Staithes.


Welcome to Greystones, a fantastic holiday property for all the family, full of original features and perfectly located in the beautiful seaside village of Staithes in North Yorksh...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £383 *

View
  • 50% off

    9 May 2025 - 16 May 2025

    From £612.00 £306.00

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

7 nights from £547

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 £547

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 £665

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 £665

Belle's View is a 2 bedroom, dog friendly apartment with sea views in Scarborough.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £498

Belle's View

5513

2 bedroom, dog friendly apartment with sea views in Scarborough.


Nestled in the perfect location near to Scarborough's north beach, Belle's View is a simply gorgeous dog-friendly apartment with fantastic sea views, ideal for a seaside holiday at...

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

7 nights from £498

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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

7 nights from £712

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 £712

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 £105 per night

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 £105 per night

Load more

Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in North Yorkshire. So have a look through our 12 holiday cottages available this May in North Yorkshire.