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 36 cottages near Helmsley.

Birchglow ref: IYT

Helmsley, near Pickering, North York Moors

£0-£1459

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5 star rating
Birchglow
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Adjacent to the renowned Feversham Arms Hotel and Verbena Spa, this holiday property is ideal for exploring coast and moors.
  • Sleeps
    6
  • Number of Pets
    0
  • Bedrooms
    3
  • Bathrooms
    3
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Ashberry Cottage ref: E1945

Rievaulx, near Helmsley, Yorkshire, North York Moors

£345-£680

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3 star rating
Idyllic riverside location, pretty cottage with woodburner and beams, close to Rievaulx Abbey, Nunnington Hall and Duncombe Park nearby.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

The Firs ref: CC233112

Helmsley, North York Moors

£472-£1393

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4 star rating
This former farmhouse is situated in the market town of Helmsley and is perfect for those wishing to explore all that the North York Moors has to offer.
  • Sleeps
    5
  • Number of Pets
    0
  • Bedrooms
    4
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Ashberry Farm Cottage ref: DC0455

Rievaulx near Helmsley, North York Moors

£265-£462

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3 star rating
Picture postcard location overlooking the duck pond.
  • Sleeps
    3
  • Number of Pets
    0
  • Bedrooms
    1
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Ash Lodge ref: W40993

Nawton, near Helmsley, North York Moors

£331-£685

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4 star rating
Detached lodge, in lovely countryside, between Helmsley and Kirkbymoorside, with Castle Howard, Duncombe Park, and York all easily accessible.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Oak Tree Cottage ref: DC4437

Kirkbymoorside, North York Moors

£416-£554

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4 star rating
Attractive converted farm buildings overlooking the Vale of Pickering. Rural area, ideal for walking and cycling.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    2
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

Finch Lodge ref: E4793

Nawton, near Helmsley, , North York Moors

£302-£642

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3 star rating
Cosy lodge with decking and country views, close to Camp Eden, York with Minster and Jorvik Viking Centre easily reached.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Cliff Stud Cottages - Frankel Cottage ref: UK2308

Helmsley, North York Moors

£451-£451

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4 star rating
Found on a stud farm, Frankel Cottage offers the perfect base to explore Helmsley and the North York Moors National Park.
  • Sleeps
    5
  • Number of Pets
    1
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Mill House ref: UK2088

Rievaulx, near Helmsley, North York Moors

£589-£1109

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4 star rating
A Grade II listed detached cottage with an open fire, set in an idyllic picturesque valley alongside the magnificent ruins of Rievaulx Abbey - a warm welcoming ambience is assured.
  • Sleeps
    5
  • Number of Pets
    2
  • Bedrooms
    3
  • Bathrooms
    2
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    2

Pockley Gates Cottage ref: CC232126

near Helmsley, North York Moors

£399-£787

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4 star rating
A quite, semi detached cottage overlooking the countryside just outside the traditional Yorkshire village of Helmsley.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    1

Cliff Stud Cottages - Cecil Cottage ref: UK2307

Helmsley, North York Moors

£451-£451

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4 star rating
Cecil Cottage is located on the renowned Cliff Stud Farm, offering wonderful views over the surrounding countryside, ideal for a relaxing holiday.
  • Sleeps
    5
  • Number of Pets
    0
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Plum Tree Cottage ref: CC232113

Kirkbymoorside, North York Moors

£301-£559

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4 star rating
This delightful single storey cottage offers cosy holiday accommodation.
  • Sleeps
    2
  • Number of Pets
    1
  • Bedrooms
    1
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    4

Bridge House ref: KOG

Helmsley, North York Moors

£436-£1244

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5 star rating
Located in the town of Helmsley, this Grade II listed house is great for visiting Helmsley Castle and Duncombe Park.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    3
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    0

Manor Farm Cottage ref: UK2058

Scawton, near Helmsley, North York Moors

£267-£523

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3 star rating
Commanding spectacular views over open countryside towards the Hambleton Hills this property is just 1½ miles from Rievaulx Abbey and has excellent footpath walks from the door.
  • Sleeps
    3
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    3

The Stables ref: 27498

Oswaldkirk, near Helmsley, North York Moors

£497-£940

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5 star rating
Enjoy views over the Howardian Hills from the large patio area and your dog will love all the walking opportunities nearby.
  • Sleeps
    6
  • Number of Pets
    3
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    3