Helmsley is a beautiful old market town and its market cross serves as the starting point of the Cleveland Way, a 108 mile trek around the North Yorkshire Moors. As such, it has plenty of amenities for the visitor. Shopping is very good in Helmsley and it also has several quality inns and pubs to cater to the visiting walkers.

Helmsley is far more than just a way station - there are several places to visit making it a good place to stay for a few days. Helmsley Castle, built in the 1200s is a great place to start. The ruins of the castle loom over the town. The castle was intact until the Civil War when it was destroyed by the Parliamentarians. The fantastic Baroque home of the Duncombe family is also worth a visit. Duncombe Park offers centuries-old treasures to view, beautiful ornamental gardens and attractions for younger visitors. These two sights are within view from Helmsley Walled Garden but do not detract from the garden itself. This five-acre site, first built in 1756, is a fully functioning kitchen garden.

Helmsley has lovely old pubs, traditional tea houses and wonderful relaxing walks by the river. In short, it is an ideal place for a short break or for a longer getaway.

Cottage distance (in Miles)
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There are 34 cottages near Helmsley.

Wren Lodge

3 star rating

Nawton, near Helmsley, , North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 2

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Price from

£327-£669

3 star rating
Nawton, near Helmsley, , North York Moors

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Price from

£327-£669

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

Plum Tree Cottage

4 star rating

Kirkbymoorside, North York Moors

  • Sleeps: 2
  • Bedrooms: 1
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£286-£582

4 star rating
Kirkbymoorside, North York Moors

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Price from

£286-£582

Sleeps: 2 Bedrooms: 1 Bathrooms: 1 Pets: 1

Highfield Barn

4 star rating

Nawton, near Helmsley, North York Moors

  • Sleeps: 2
  • Bedrooms: 1
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 2

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Price from

£319-£555

4 star rating
Nawton, near Helmsley, North York Moors

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Price from

£319-£555

Sleeps: 2 Bedrooms: 1 Bathrooms: 1 Pets: 0

Honeysuckle Cottage

4 star rating

Helmsley, York, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 0

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Price from

£446-£1025

4 star rating
Helmsley, York, North York Moors

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Price from

£446-£1025

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 0

Swiss Cottage

4 star rating

Rievaulx, near Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 2
  • Number of Pets: 2
  • Distance from Helmsley (miles): 2

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Price from

£582-£1449

4 star rating
Rievaulx, near Helmsley, North York Moors

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Price from

£582-£1449

Sleeps: 4 Bedrooms: 2 Bathrooms: 2 Pets: 2

Finch Lodge

3 star rating

Nawton, near Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 2

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Price from

£251-£635

3 star rating
Nawton, near Helmsley, North York Moors

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Price from

£251-£635

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

Bridge House

5 star rating

Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 3
  • Number of Pets: 0
  • Distance from Helmsley (miles): 0

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Price from

£401-£1325

5 star rating
Helmsley, North York Moors

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Price from

£401-£1325

Sleeps: 4 Bedrooms: 2 Bathrooms: 3 Pets: 0

Camomile Cottage

0 star rating

Nunnington, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 0
  • Distance from Helmsley (miles): 4

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Price from

£359-£759

0 star rating
Nunnington, North York Moors

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Price from

£359-£759

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 0

Honeysuckle Cottage

0 star rating

Oswaldkirk, near Helmsley, North York Moors

  • Sleeps: 3
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 3

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Price from

£428-£675

0 star rating
Oswaldkirk, near Helmsley, North York Moors

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Price from

£428-£675

Sleeps: 3 Bedrooms: 2 Bathrooms: 1 Pets: 1

Elm Tree Cottage

4 star rating

Kirkbymoorside, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£349-£680

4 star rating
Kirkbymoorside, North York Moors

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Price from

£349-£680

Sleeps: 4 Bedrooms: 2 Bathrooms: 1 Pets: 1

Colville House

3 star rating

Helmsley, North York Moors

  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 0

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Price from

£288-£999

3 star rating
Helmsley, North York Moors

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Price from

£288-£999

Sleeps: 6 Bedrooms: 3 Bathrooms: 1 Pets: 1

Mill House

4 star rating

Rievaulx, near Helmsley, North York Moors

  • Sleeps: 5
  • Bedrooms: 3
  • Bathrooms: 2
  • Number of Pets: 2
  • Distance from Helmsley (miles): 2

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Price from

£669-£1649

4 star rating
Rievaulx, near Helmsley, North York Moors

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Price from

£669-£1649

Sleeps: 5 Bedrooms: 3 Bathrooms: 2 Pets: 2

Manor Cottage

4 star rating

Old Byland, near Helmsley, North York Moors

  • Sleeps: 8
  • Bedrooms: 4
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£333-£1035

4 star rating
Old Byland, near Helmsley, North York Moors

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Price from

£333-£1035

Sleeps: 8 Bedrooms: 4 Bathrooms: 1 Pets: 1

Ash Tree Cottage

4 star rating

near Kirkbymoorside, North York Moors

  • Sleeps: 3
  • Bedrooms: 2
  • Bathrooms: 1
  • Number of Pets: 1
  • Distance from Helmsley (miles): 4

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Price from

£404-£650

4 star rating
near Kirkbymoorside, North York Moors

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Price from

£404-£650

Sleeps: 3 Bedrooms: 2 Bathrooms: 1 Pets: 1

Clyde Cottage

4 star rating

Nawton near Helmsley, North York Moors

  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 2
  • Number of Pets: 0
  • Distance from Helmsley (miles): 2

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Price from

£374-£669

4 star rating
Nawton near Helmsley, North York Moors

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Price from

£374-£669

Sleeps: 4 Bedrooms: 2 Bathrooms: 2 Pets: 0