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

Living area | Lily Pad, Helmsley

Helmsley, Yorkshire

Lily Pad

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£545
View
Reserve today for only £25
Exterior | Tiggywinkle Cottage, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Tiggywinkle Cottage

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£625
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£655
View
Reserve today for only £25
Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, Yorkshire

Home Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 5
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£489
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 3 bathrooms
  • Up to 1 pet allowed

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Open plan living space | Rosebeck, Helmsley

Helmsley, Yorkshire

Rosebeck

Wifi
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£459
View
Exterior | Robin Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, Yorkshire

Robin Lodge

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£375
View
Reserve today for only £25
Exterior | Pheasant Lodge, Wombleton, near Helmsley

Wombleton, near Helmsley, Yorkshire

Pheasant Lodge

Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£615
View
Exterior | Highfield Barn, Scackleton, nr. Hovingham

Scackleton, near Hovingham, Yorkshire

Highfield Barn

Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.4

out of 5

7 nights

From

£335
View
Reserve today for only £25
Exterior | Ristbrow Farm, Hawnby

Hawnby, Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • Sleeps up to 12
  • 6 bedrooms
  • 4 bathrooms
  • Up to 3 pets allowed

4.9

out of 5

7 nights

From

£1,799
View
Silent Springs, Nawton, near Helmsley

Nawton, near Helmsley, Yorkshire

Silent Springs

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.8

out of 5

7 nights

From

£455
View
Reserve today for only £25
Exterior | The Nab, Pockley, near Helmsley

Pockley, near Helmsley, Yorkshire

The Nab

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£405
View

Dog Friendly Helmsley Cottages

Exterior | Tiggywinkle Cottage, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Tiggywinkle Cottage

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£625
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£655
View
Reserve today for only £25
Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, Yorkshire

Home Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 5
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£489
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 3 bathrooms
  • Up to 1 pet allowed

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Open plan living space | Rosebeck, Helmsley

Helmsley, Yorkshire

Rosebeck

Wifi
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£459
View
Exterior | Robin Lodge - Valley View Lodges, Nawton, near Helmsley

Nawton, near Helmsley, Yorkshire

Robin Lodge

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£375
View
Reserve today for only £25
Exterior | Highfield Barn, Scackleton, nr. Hovingham

Scackleton, near Hovingham, Yorkshire

Highfield Barn

Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.4

out of 5

7 nights

From

£335
View
Reserve today for only £25
Exterior | Ristbrow Farm, Hawnby

Hawnby, Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • Sleeps up to 12
  • 6 bedrooms
  • 4 bathrooms
  • Up to 3 pets allowed

4.9

out of 5

7 nights

From

£1,799
View
Silent Springs, Nawton, near Helmsley

Nawton, near Helmsley, Yorkshire

Silent Springs

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.8

out of 5

7 nights

From

£455
View
Reserve today for only £25
Exterior | The Nab, Pockley, near Helmsley

Pockley, near Helmsley, Yorkshire

The Nab

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£405
View
Exterior | The Nest, Helmsley

Helmsley, Yorkshire

The Nest

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.7

out of 5

7 nights

From

£349
View
Bedroom | The Dreamer’s Hut, Hawnby

Hawnby, Yorkshire

The Dreamer’s Hut

Hot Tub
Wifi
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.8

out of 5

7 nights

From

£995
View
Reserve today for only £25

Luxury Helmsley Cottages

Open plan living space | Rye Cottage, Helmsley

Helmsley, Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 3 bathrooms
  • Up to 1 pet allowed

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Exterior | Bridge House, Helmsley

Helmsley, Yorkshire

Bridge House

Luxury
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 3 bathrooms
  • Up to 0 pets allowed

3

out of 5

7 nights

From

£429
View
Reserve today for only £25
Exterior | Pheasant Lodge, Wombleton, near Helmsley

Wombleton, near Helmsley, Yorkshire

Pheasant Lodge

Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£615
View
Exterior | Ristbrow Farm, Hawnby

Hawnby, Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • Sleeps up to 12
  • 6 bedrooms
  • 4 bathrooms
  • Up to 3 pets allowed

4.9

out of 5

7 nights

From

£1,799
View
Garden | Mill House, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Mill House

Hot Tub
Luxury
Wifi
  • Sleeps up to 6
  • 4 bedrooms
  • 4 bathrooms
  • Up to 2 pets allowed

4.7

out of 5

7 nights

From

£705
View
Exterior | The Cart House, Helmsley

Helmsley, Yorkshire

The Cart House

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.7

out of 5

7 nights

From

£895
View
Reserve today for only £25
Alternative level accesss available’ | Todd’s Pasture, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Todd’s Pasture

Hot Tub
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 4 bathrooms
  • Up to 3 pets allowed

4.8

out of 5

7 nights

From

£1,959
View
Outdoor area | The Helmsley Retreat, Helmsley, near York

Helmsley, near York, Yorkshire

The Helmsley Retreat

Hot Tub
Luxury
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£665
View

Romantic Helmsley Cottages

Living area | Lily Pad, Helmsley

Helmsley, Yorkshire

Lily Pad

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£545
View
Reserve today for only £25
Exterior | Tiggywinkle Cottage, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Tiggywinkle Cottage

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£625
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£655
View
Reserve today for only £25
Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, Yorkshire

Home Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 5
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£489
View
Open plan living space | Rye Cottage, Helmsley

Helmsley, Yorkshire

Rye Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 3 bathrooms
  • Up to 1 pet allowed

4.2

out of 5

7 nights

From

£805
View
Reserve today for only £25
Exterior | Bridge House, Helmsley

Helmsley, Yorkshire

Bridge House

Luxury
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 3 bathrooms
  • Up to 0 pets allowed

3

out of 5

7 nights

From

£429
View
Reserve today for only £25
Open plan living space | Rosebeck, Helmsley

Helmsley, Yorkshire

Rosebeck

Wifi
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£459
View
Exterior | Ristbrow Farm, Hawnby

Hawnby, Yorkshire

Ristbrow Farm

Hot Tub
Luxury
Wifi
  • Sleeps up to 12
  • 6 bedrooms
  • 4 bathrooms
  • Up to 3 pets allowed

4.9

out of 5

7 nights

From

£1,799
View
Bedroom | The Dreamer’s Hut, Hawnby

Hawnby, Yorkshire

The Dreamer’s Hut

Hot Tub
Wifi
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.8

out of 5

7 nights

From

£995
View
Reserve today for only £25
Exterior | Ashberry Cottage, Rievaulx, nr. Helmsley

Rievaulx, near Helmsley, Yorkshire

Ashberry Cottage

Car parking on site
Enclosed Garden / Patio
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£449
View
Reserve today for only £25
Exterior | The Byre, Helmsley

Helmsley, Yorkshire

The Byre

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 3 pets allowed

4.8

out of 5

7 nights

From

£409
View
Reserve today for only £25
Exterior | Lawns Cottage, Sproxton, near Helmsley

Sproxton, near Helmsley, Yorkshire

Lawns Cottage

Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£505
View
Reserve today for only £25

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

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Explore

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