Destinations and properties
Dates and flexibility
Select dates
Party makeup
Guests
Helmsley • Dates • Guests
Helmsley • Dates • Guests

Filters


Price range

Based on a 7 night stay

£350
£1,500+
Reset

Property makeup

Dogs allowed



Minimum star grading



Property type

Helmsley holiday cottages

103 properties found
Chop Gate, near Stokesley, Yorkshire

Owl Cottage - Chop Gate

2111

Our grading

7 nights

£503 - £780

View
Osmotherley, near Northallerton, Yorkshire

Vane House Cottage

2111

Our grading

7 nights

£474 - £763

View
Chop Gate, near Stokesley, Yorkshire

Meadow Hideaway

2112

Our grading

7 nights

£903 - £1,126

View
Helmsley, Yorkshire

Cosy Barn - Helmsley

211

Our grading

7 nights

£684 - £805

View
Carlton-in-Cleveland near Stokesley, Yorkshire

Wainstones Lodge

211

Our grading

7 nights

£671 - £1,377

View

Keep me updated with new properties, holiday ideas and special offers!

Please enter a valid email address.

At Gorgeous Cottages, part of The Travel Chapter Group, your privacy is paramount to us. You can read in our privacy statement how we safeguard your data. You can opt out at any time.

Carlton-in-Cleveland near Stokesley, Yorkshire

Coldmoor Lodge

210

Our grading

7 nights

£671 - £1,377

View
Carlton-in-Cleveland near Stokesley, Yorkshire

Carlton Lodge

211

Our grading

7 nights

£671 - £1,377

View
Helmsley, Yorkshire

Coco

3212

Our grading

7 nights

£744 - £1,300

View
Helmsley, Yorkshire

Ferne Cottage - Helmsley

3212

Our grading

7 nights

£724 - £1,300

View
Helmsley, Yorkshire

The Velveteen Bath House

4232

Our grading

7 nights

£1,105 - £2,261

View
South Kilvington, near Thirsk, Yorkshire

Grange View Cottage - Thirsk

4213

Our grading

7 nights

£744 - £1,249

View
Thimbleby, near Northallerton, Yorkshire

Webstone Cottage

4212

Our grading

7 nights

£627 - £1,074

View
23...9

Showing 1-12 of 103 properties

Self-catering holiday accommodation in Helmsley

Stay in a luxury holiday home in Helmsley on your getaway to Yorkshire. Helmsley is a traditional English market town with a stately square, castle ruins, enticing cafes and tearooms, and old-fashioned pubs where you can drink local ales from tankards. The only market town in the North York Moors National Park, our holiday cottages in Helmsley offer the perfect base for outdoor adventures, but there’s also plenty of things to do in Helmsley right from your front door.

Helmsley has a reputation as being a creative town, home to the Helmsley Arts Centre which hosts a fine selection of pantomimes, films, dance, theatre, art workshops and events throughout the year. And on a warm, sunny day, nothing beats a refreshing dip in Helmsley’s Open Air Swimming Pool, which is open from June until September.

A luxury Helmsley staycation

A stay in one of our Helmsley luxury holiday cottages is guaranteed to delight couples and families alike, as there is plenty to enchant keen walkers, budding historians and leisure seekers throughout this fantastic location. We have dog-friendly Helmsley cottages so your best friend can come along too or browse our full range of North Yorkshire cottages to discover even more market towns and pretty villages.