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 | 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
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

4.7

out of 5

7 nights

From

£625
View
Reserve today for only £25
Living area | Lily Pad, Helmsley

Helmsley, North Yorkshire

Lily Pad

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

4.7

out of 5

7 nights

From

£537
View
Reserve today for only £25
Attractive holiday home | Grange Cottage, Harome, near Helmsley

Harome, near Helmsley, North Yorkshire

Grange Cottage

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

4.8

out of 5

7 nights

From

£695
View
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 | 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 | 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
Beautiful semi-detached holiday home | Ashberry Farm Cottage, Rievaulx near Helmsley

Rievaulx near Helmsley, North Yorkshire

Ashberry Farm Cottage

Car parking on site
Garden / Patio
  • 3 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£303
View
Exterior | Silent Springs, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Silent Springs

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

4.8

out of 5

7 nights

From

£417
View
Reserve today for only £25
Exterior | Borough Beck Cottage, Helmsley

Helmsley, North Yorkshire

Borough Beck Cottage

Wifi
Pub within 1 mile
Garden / Patio
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.8

out of 5

7 nights

From

£407
View
Exterior | Wren Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Wren Lodge

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

5

out of 5

7 nights

From

£383
View
Reserve today for only £25
Exterior | Tiggywinkle Cottage, Hawnby, near Helmsley

Hawnby, near Helmsley, North Yorkshire

Tiggywinkle Cottage

Hot Tub
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

7 nights

From

£609
View

Dog Friendly Helmsley Cottages

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
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

4.7

out of 5

7 nights

From

£625
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 | 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 | Ridings Cottage, Helmsley

Helmsley, North Yorkshire

Ridings Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

7 nights

From

£649
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

£1,330
View
Reserve today for only £25
Exterior | Silent Springs, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Silent Springs

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

4.8

out of 5

7 nights

From

£417
View
Reserve today for only £25
Exterior | Borough Beck Cottage, Helmsley

Helmsley, North Yorkshire

Borough Beck Cottage

Wifi
Pub within 1 mile
Garden / Patio
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.8

out of 5

7 nights

From

£407
View
Exterior | Wren Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, North Yorkshire

Wren Lodge

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

5

out of 5

7 nights

From

£383
View
Reserve today for only £25
Exterior | Tiggywinkle Cottage, Hawnby, near Helmsley

Hawnby, near Helmsley, North Yorkshire

Tiggywinkle Cottage

Hot Tub
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

7 nights

From

£609
View
Exterior | The Byre, Helmsley

Helmsley, North Yorkshire

The Byre

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

4.6

out of 5

7 nights

From

£387
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

£845
View
Reserve today for only £25

Luxury Helmsley Cottages

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
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

4.7

out of 5

7 nights

From

£625
View
Reserve today for only £25
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 | Lockton House, Helmsley

Helmsley, North Yorkshire

Lockton House

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

7 nights

From

£1,330
View
Reserve today for only £25
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

3

out of 5

7 nights

From

£353
View
Reserve today for only £25
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

4.8

out of 5

7 nights

From

£1,990
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

4.3

out of 5

7 nights

From

£805
View
Reserve today for only £25
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
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

4.6

out of 5

7 nights

From

£695
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.

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