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Helmsley cottages

This charming market town lies on the edge of the North York Moors National Park. With access to some of the most breathtaking landscapes of mile after mile of rolling heather moors, right on your doorstep. With its fascinating history, many of the buildings date back to the 17th century, the town's medieval castle dominates the skyline high up on its grassy knoll. Sit back and relax in one of the cosy pubs or inns that surround the town square. If the weather is being kind take a dip in the town's open-air swimming pool. Explore our selection of Helmsley cottages to find the perfect break for you and your family. Needing suggestions for things to see and do? Scroll down for our top 5 activities in the area.

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Helmsley cottages

Popular Helmsley cottages

Exterior | The Cart House, Helmsley
Customers' Choice

Helmsley, Yorkshire

The Cart House

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

4.7

out of 5

6 nights

From

£819
View
Living room | Honeysuckle Cottage, Helmsley, York

Helmsley, York, Yorkshire

Honeysuckle Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.5

out of 5

4 nights

From

£695
View
Open plan living space | Popleys, Helmsley
Customers' Choice

Helmsley, Yorkshire

Popleys

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

5 nights

From

£639
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

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

4.8

out of 5

5 nights

From

£635
View
Exterior | Ristbrow Farm, Hawnby
Customers' Choice

Hawnby, Yorkshire

Ristbrow Farm

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

4.9

out of 5

12 nights

From

£1,325
View
Attractive holiday home | Grange Cottage, Harome, near Helmsley
Customers' Choice

Harome, near Helmsley, Yorkshire

Grange Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

6 nights

From

£455
View
Attractive holiday home | Crossbill Cottage, Chopgate near Stokesley
Customers' Choice

Chopgate near Stokesley, Yorkshire

Crossbill Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 3
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

3 nights

From

£399
View
Hot tub | The Dreamer’s Hut, Hawnby

Hawnby, Yorkshire

The Dreamer’s Hut

Pets stay free
Hot Tub
Wifi
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

2 nights

From

£895
View
Exterior | Frankel Cottage - Cliff Stud Retreat, Helmsley

Helmsley, Yorkshire

Frankel Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.7

out of 5

5 nights

From

£750
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 0 pets allowed

4.6

out of 5

2 nights

From

£285
View
Charming holiday home | Foxglove Cottage - Laskill Grange, Bilsdale, near Helmsley

Bilsdale, near Helmsley, Yorkshire

Laskill Grange - Foxglove Cottage

Pets stay free
Wifi
Detached
Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£279
View
Exterior | Rievaulx Cottage - Laskill Grange, Bilsdale, near Helmsley

Bilsdale, near Helmsley, Yorkshire

Laskill Grange - Rievaulx Cottage

Pets stay free
Wifi
Car parking on site
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£225
View

Dog friendly Helmsley cottages

Exterior | The Cart House, Helmsley
Customers' Choice

Helmsley, Yorkshire

The Cart House

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

4.7

out of 5

6 nights

From

£819
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

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

4.8

out of 5

5 nights

From

£635
View
Exterior | The Garth, Helmsley

Helmsley, Yorkshire

The Garth

Pets stay free
Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5 nights

From

£455
View
Exterior | Ristbrow Farm, Hawnby
Customers' Choice

Hawnby, Yorkshire

Ristbrow Farm

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

4.9

out of 5

12 nights

From

£1,325
View
Hot tub | The Dreamer’s Hut, Hawnby

Hawnby, Yorkshire

The Dreamer’s Hut

Pets stay free
Hot Tub
Wifi
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

2 nights

From

£895
View
Exterior | Frankel Cottage - Cliff Stud Retreat, Helmsley

Helmsley, Yorkshire

Frankel Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.7

out of 5

5 nights

From

£750
View
Charming holiday home | Foxglove Cottage - Laskill Grange, Bilsdale, near Helmsley

Bilsdale, near Helmsley, Yorkshire

Laskill Grange - Foxglove Cottage

Pets stay free
Wifi
Detached
Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£279
View
Exterior | Rievaulx Cottage - Laskill Grange, Bilsdale, near Helmsley

Bilsdale, near Helmsley, Yorkshire

Laskill Grange - Rievaulx Cottage

Pets stay free
Wifi
Car parking on site
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£225
View
3.5 acre garden with furniture and built in barbeque | The Lodge Cottage, Hovingham

Hovingham, Yorkshire

The Lodge Cottage

Pets stay free
Wifi
Car parking on site
Detached
  • Sleeps up to 7
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£749
View
Delightful living area with a wood burner | The Forge - Laskill Grange, Bilsdale, near Helmsley

Bilsdale, near Helmsley, Yorkshire

Laskill Grange - The Forge

Pets stay free
Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

6 nights

From

£425
View
Colville House, Helmsley

Helmsley, Yorkshire

Colville House

Car parking on site
Pub within 1 mile
Detached
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.8

out of 5

6 nights

From

£309
View
Exterior | Home Cottage, Hovingham, near Helmsley

Hovingham, near Helmsley, Yorkshire

Home Cottage

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

4.6

out of 5

5 nights

From

£365
View

Luxury Helmsley cottages

Exterior | The Cart House, Helmsley
Customers' Choice

Helmsley, Yorkshire

The Cart House

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

4.7

out of 5

6 nights

From

£819
View
Living room | Honeysuckle Cottage, Helmsley, York

Helmsley, York, Yorkshire

Honeysuckle Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.5

out of 5

4 nights

From

£695
View
Exterior | Ristbrow Farm, Hawnby
Customers' Choice

Hawnby, Yorkshire

Ristbrow Farm

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

4.9

out of 5

12 nights

From

£1,325
View
Exterior | Frankel Cottage - Cliff Stud Retreat, Helmsley

Helmsley, Yorkshire

Frankel Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.7

out of 5

5 nights

From

£750
View
Open plan living space | Forge Cottage - Coxwold Cottages, Coxwold, near Helmsley

Coxwold, near Helmsley, Yorkshire

Coxwold Cottages - Forge Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

2 nights

From

£1,351
View
Outdoor area | The Helmsley Retreat, Helmsley, near York

Helmsley, near York, Yorkshire

The Helmsley Retreat

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

4.7

out of 5

4 nights

From

£595
View
Outstanding holiday home | Todd’s Pasture, Hawnby, near Helmsley
Customers' Choice

Hawnby, near Helmsley, Yorkshire

Todd’s Pasture

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

4.9

out of 5

8 nights

From

£1,525
View
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

4 nights

From

£489
View
Exterior | Mill House, Hawnby, near Helmsley

Hawnby, near Helmsley, Yorkshire

Mill House

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 4 bathrooms
  • Up to 2 pets allowed

4.8

out of 5

8 nights

From

£739
View

Romantic Helmsley cottages

Exterior | The Cart House, Helmsley
Customers' Choice

Helmsley, Yorkshire

The Cart House

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

4.7

out of 5

6 nights

From

£819
View
Living room | Honeysuckle Cottage, Helmsley, York

Helmsley, York, Yorkshire

Honeysuckle Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.5

out of 5

4 nights

From

£695
View
Exterior | Mill House - Rievaulx Cottages, Rievaulx, near Helmsley

Rievaulx, near Helmsley, Yorkshire

Mill House

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

4.8

out of 5

5 nights

From

£635
View
Exterior | Ristbrow Farm, Hawnby
Customers' Choice

Hawnby, Yorkshire

Ristbrow Farm

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

4.9

out of 5

12 nights

From

£1,325
View
Attractive holiday home | Grange Cottage, Harome, near Helmsley
Customers' Choice

Harome, near Helmsley, Yorkshire

Grange Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

6 nights

From

£455
View
Attractive holiday home | Crossbill Cottage, Chopgate near Stokesley
Customers' Choice

Chopgate near Stokesley, Yorkshire

Crossbill Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 3
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

3 nights

From

£399
View
Hot tub | The Dreamer’s Hut, Hawnby

Hawnby, Yorkshire

The Dreamer’s Hut

Pets stay free
Hot Tub
Wifi
Detached
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

2 nights

From

£895
View
Exterior | Frankel Cottage - Cliff Stud Retreat, Helmsley

Helmsley, Yorkshire

Frankel Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.7

out of 5

5 nights

From

£750
View
3.5 acre garden with furniture and built in barbeque | The Lodge Cottage, Hovingham

Hovingham, Yorkshire

The Lodge Cottage

Pets stay free
Wifi
Car parking on site
Detached
  • Sleeps up to 7
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£749
View
Light and airy dining area with access to patio | Toad Hall, Helmsley

Helmsley, Yorkshire

Toad Hall

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

4.1

out of 5

4 nights

From

£515
View
Exterior | Sycamore Cottage, Harome, near Helmsley

Harome, near Helmsley, Yorkshire

Sycamore Cottage

Wifi
Pub within 1 mile
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

4 nights

From

£675
View
Open plan living space | Forge Cottage - Coxwold Cottages, Coxwold, near Helmsley

Coxwold, near Helmsley, Yorkshire

Coxwold Cottages - Forge Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

2 nights

From

£1,351
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. Here are the top five things to see and do in our cottages in Helmsley:

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

Explore

Destinations