Holiday cottages for September in Yorkshire

Holiday cottages for September in Yorkshire

If Septembers past are anything to go by, this is often one of the loveliest months to enjoy a holiday cottage in Yorkshire. Read more

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

We have 20 Yorkshire holiday cottages available in September.

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

7 nights from £702

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 £702

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 £98 per night

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 £98 per night

Low Rigg is a 3 bedroom, dog friendly self catering cottage in Muker.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £651

Low Rigg

5770

3 bedroom, dog friendly self catering cottage in Muker.


Come and enjoy a break in the Yorkshire Dales and relax with the rustic charm of an original Yorkshire stone cottage. Semi-detached Low Rigg is huddled at the edge the charming vil...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £651

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

7 nights from £1172 *

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 £1172 *

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

7 nights from £928

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 £928

The Old Farmhouse is a 3 bedroom, dog friendly self catering cottage in Pickering.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1096

The Old Farmhouse

5792

3 bedroom, dog friendly self catering cottage in Pickering.


Nestled on the edge of the North York Moors in the charming town of Pickering, this Grade II Listed terraced cottage effortlessly combines historic charm with contemporary luxury. ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1096

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

7 nights from £1059 *

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 £1059 *

Joe House is a 2 bedroom self catering cottage near Hawes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £594

Joe House

5779

2 bedroom self catering cottage near Hawes.


If you are looking for a cottage with a true country feel and a location to match, Joe House is for you. Set in a picturesque hamlet only a couple of minutes from the quaint villag...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £594

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

Chestnut Retreat is a 2 bedroom self catering apartment in Ossett
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1500

Chestnut Retreat

5750

2 bedroom self catering apartment in Ossett


Visit West Yorkshire and relax in this luxury apartment. After a day of visiting local attractions or walking in the hills, return to spend some quality time in the environmentally...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1500

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 £521

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 £521

Load more

The beaches are still peachy, the sea's had all summer to warm up and the schools have gone back. So you can have more sand, more cliffs and more moor to yourself. Use the search options on the left to choose your holiday dates. We've got 20 holiday cottages in Yorkshire available for your September break.