Helmsley Cottages

This charming market town nestled in the rolling hills of North Yorkshire, offers a perfect blend of history, culture, and natural beauty. With its picturesque streets lined with historic buildings, quaint shops, and welcoming cafes, it's the ideal destination for a leisurely retreat. Whether you're exploring the imposing ruins of Helmsley Castle, strolling through the peaceful grounds of Duncombe Park, or indulging in a spot of retail therapy at the town's boutique shops, there's something for everyone to enjoy. Plus, with its proximity to the stunning North York Moors National Park, outdoor enthusiasts can take advantage of the numerous walking trails and scenic viewpoints nearby. And don't forget to sample some local delicacies at one of Helmsley's charming eateries before you leave. Looking for your next home away from home, then search our selection of Helmsley cottages for inspiration.

Helmsley village

Popular Helmsley Cottages

Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, North Yorkshire

Home Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • 5 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

7 nights

From

£447
View
Reserve today for only £25
Exterior | Robin Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Robin Lodge

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£367
View
Reserve today for only £25
Exterior | Holly-Garth, Helmsley

Helmsley, North Yorkshire

Holly-Garth

Wifi
Car parking on site
Pub within 1 mile
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

4.6

out of 5

7 nights

From

£885
View
Open plan living space | Rosebeck, Helmsley

Helmsley, North Yorkshire

Rosebeck

Wifi
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

5

out of 5

7 nights

From

£453
View
Exterior | Pheasant Lodge, Wombleton, near Helmsley

Wombleton, near Helmsley, North Yorkshire

Pheasant Lodge

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£615
View
Exterior | Moorhouse Farm Cottage, Hovingham, near York

Hovingham, near York, North Yorkshire

Moorhouse Farm Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.3

out of 5

7 nights

From

£473
View
Exterior | Ristbrow Farm, Hawnby

Hawnby, North Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • 12 Guests
  • 6 Bedrooms
  • 4 Bathrooms
  • 3 Pets

4.9

out of 5

7 nights

From

£1,804
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, North Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Exterior | The Garth, Helmsley

Helmsley, North Yorkshire

The Garth

Wifi
Car parking on site
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.7

out of 5

7 nights

From

£513
View
Exterior | Feather Holme Farm Cottage, near Helmsley

near Helmsley, North Yorkshire

Feather Holme Farm Cottage

Car parking on site
Garden / Patio
Rural Location
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4

out of 5

7 nights

From

£427
View
Reserve today for only £25
Exterior | Highfield Barn, Scackleton, nr. Hovingham

Scackleton, near Hovingham, North Yorkshire

Highfield Barn

Wifi
Car parking on site
Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.5

out of 5

7 nights

From

£323
View
Reserve today for only £25
Exterior | Lawns Cottage, Sproxton, near Helmsley

Sproxton, near Helmsley, North Yorkshire

Lawns Cottage

Wifi
Car parking on site
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.5

out of 5

7 nights

From

£463
View

Dog Friendly Helmsley Cottages

Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, North Yorkshire

Home Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • 5 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

7 nights

From

£447
View
Reserve today for only £25
Exterior | Robin Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Robin Lodge

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£367
View
Reserve today for only £25
Exterior | Holly-Garth, Helmsley

Helmsley, North Yorkshire

Holly-Garth

Wifi
Car parking on site
Pub within 1 mile
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

4.6

out of 5

7 nights

From

£885
View
Open plan living space | Rosebeck, Helmsley

Helmsley, North Yorkshire

Rosebeck

Wifi
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

5

out of 5

7 nights

From

£453
View
Exterior | Moorhouse Farm Cottage, Hovingham, near York

Hovingham, near York, North Yorkshire

Moorhouse Farm Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.3

out of 5

7 nights

From

£473
View
Exterior | Ristbrow Farm, Hawnby

Hawnby, North Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • 12 Guests
  • 6 Bedrooms
  • 4 Bathrooms
  • 3 Pets

4.9

out of 5

7 nights

From

£1,804
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, North Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Exterior | The Garth, Helmsley

Helmsley, North Yorkshire

The Garth

Wifi
Car parking on site
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.7

out of 5

7 nights

From

£513
View
Exterior | Feather Holme Farm Cottage, near Helmsley

near Helmsley, North Yorkshire

Feather Holme Farm Cottage

Car parking on site
Garden / Patio
Rural Location
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4

out of 5

7 nights

From

£427
View
Reserve today for only £25
Exterior | Highfield Barn, Scackleton, nr. Hovingham

Scackleton, near Hovingham, North Yorkshire

Highfield Barn

Wifi
Car parking on site
Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.5

out of 5

7 nights

From

£323
View
Reserve today for only £25
Exterior | Lawns Cottage, Sproxton, near Helmsley

Sproxton, near Helmsley, North Yorkshire

Lawns Cottage

Wifi
Car parking on site
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.5

out of 5

7 nights

From

£463
View
Outdoor area | The Helmsley Retreat, Helmsley, near York

Helmsley, near York, North Yorkshire

The Helmsley Retreat

Hot Tub
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

7 nights

From

£665
View

Luxury Helmsley Cottages

Exterior | Pheasant Lodge, Wombleton, near Helmsley

Wombleton, near Helmsley, North Yorkshire

Pheasant Lodge

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£615
View
Exterior | Ristbrow Farm, Hawnby

Hawnby, North Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • 12 Guests
  • 6 Bedrooms
  • 4 Bathrooms
  • 3 Pets

4.9

out of 5

7 nights

From

£1,804
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, North Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Outdoor area | The Helmsley Retreat, Helmsley, near York

Helmsley, near York, North Yorkshire

The Helmsley Retreat

Hot Tub
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

7 nights

From

£665
View
Exterior | Bridge House, Helmsley

Helmsley, North Yorkshire

Bridge House

Luxury
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • 0 Pets

2.8

out of 5

7 nights

From

£413
View
Reserve today for only £25
Exterior | The Cart House, Helmsley

Helmsley, North Yorkshire

The Cart House

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.7

out of 5

7 nights

From

£895
View
Reserve today for only £25
Exterior | Lockton House, Helmsley

Helmsley, North Yorkshire

Lockton House

Hot Tub
Luxury
Wifi
  • 9 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 2 Pets

7 nights

From

£1,350
View
Reserve today for only £25
Garden | Mill House, Hawnby, near Helmsley

Hawnby, near Helmsley, North Yorkshire

Mill House

Hot Tub
Luxury
Wifi
  • 6 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 2 Pets

4.7

out of 5

7 nights

From

£695
View
Alternative level accesss available’ | Todd’s Pasture, Hawnby, near Helmsley

Hawnby, near Helmsley, North Yorkshire

Todd’s Pasture

Hot Tub
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 3 Pets

4.9

out of 5

7 nights

From

£1,990
View

Inspiration of things to see and do in our cottages in Helmsley

This picturesque market town in North Yorkshire offers a blend of history, natural beauty, and charming attractions. With the largest collection of Yorkshire cottages, we have the perfect home away from home for you.

Here are the top five things to see and do in our cottages in Helmsley:

Helmsley Castle

Explore Helmsley Castle, a medieval fortress with well-preserved ruins. Climb to the top of the tower for panoramic views of the town and the surrounding countryside.

Rievaulx Abbey

Visit Rievaulx Abbey, a stunning Cistercian monastery located just a short drive from Helmsley. Walk among the atmospheric ruins and appreciate the tranquillity of this historic site.

Duncombe Park

Discover Duncombe Park, a magnificent stately home surrounded by beautiful gardens and parkland. Take a leisurely stroll through the landscaped grounds and enjoy the peaceful atmosphere.

Helmsley Walled Garden

Enjoy the beauty of Helmsley Walled Garden, a five-acre site restored to its former glory. The garden features a wide variety of plants, flowers, and themed areas to explore.

North York Moors National Park

Explore the stunning landscapes of the North York Moors National Park, which surrounds Helmsley. Go for scenic walks, enjoy cycling routes, or simply appreciate the beauty of this expansive national park.

More Popular Holiday Destinations

Holmfirth cottages

Kettlewell cottages

Bridlington cottages

Harrogate cottages

Helmsley village

Explore

A father hugging his son

Sign up for a chance to win £500!

Stay updated on the latest deals, exclusive offers and new holiday destinations by joining the cottages.com newsletter! Register today and automatically be entered into our prize draw to win a £500 voucher.

Click here for terms and conditions. You can opt out anytime by using the unsubscribe link in our emails. We will use your information as per our Privacy Notice.