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.

Swiss Cottage ref: DC5480

Rievaulx, near Helmsley, North York Moors

£531-£895

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Swiss Cottage
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This beautiful 17th century detached thatched cottage overlooks Rievalux Abbey.
  • Sleeps
    4
  • Number of Pets
    2
  • Bedrooms
    2
  • Bathrooms
    2
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    2

Cliff Stud Cottages - Frankel Cottage ref: UK2308

Helmsley, North York Moors

£451-£926

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
New!
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

Ashberry Farm Cottage ref: DC0455

Rievaulx near Helmsley, North York Moors

£257-£462

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

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

Highfield Barn ref: DC4694

Helmsley, North York Moors

£303-£554

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Beautifully presented cottage within a peaceful location
  • Sleeps
    2
  • Number of Pets
    0
  • Bedrooms
    1
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Camomile Cottage ref: 19797

Nunnington, North York Moors

£359-£737

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    4

Ryecroft ref: CC233019

Nunnington near Helmsley, North York Moors

£491-£983

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Beautiful fully renovated cottage with paddock in a quiet village– ideal for families
  • Sleeps
    6
  • Number of Pets
    0
  • Bedrooms
    3
  • Bathrooms
    2
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

Clyde Cottage ref: CC232125

Nawton near Helmsley, North York Moors

£354-£629

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Near Helmsley and Kirkbymoorside this stable conversion is an ideal base to discover the area.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    2
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Elm Tree Cottage ref: CC232112

Kirkbymoorside, North York Moors

£399-£652

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
This delightful conversion provides a well equipped holiday accommodation.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    4

Cliff Stud Cottages - Cecil Cottage ref: UK2307

Helmsley, North York Moors

£451-£926

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
New!
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

Ash Tree Cottage ref: DC5386

near Kirkbymoorside, North York Moors

£383-£605

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Character courtyard cottage with walks direct from the doorstep.
  • Sleeps
    3
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

Honeysuckle Cottage ref: ISV

Helmsley, York, North York Moors

£461-£995

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
With a wealth of beams, this cottage has a south-facing garden and makes an excellent base for exploring.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    0

Plum Tree Cottage ref: CC232113

Kirkbymoorside, North York Moors

£327-£559

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

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

Colville House ref: 19181

Helmsley, North York Moors

£339-£973

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

3 star rating
Enjoy exploring Runswick Bay and Robin Hoods Bay, well as Whitby and York from this comfortable detached house.
  • Sleeps
    6
  • Number of Pets
    1
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Hunters Cottage ref: 26343

Helmsley, North York Moors

£318-£722

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
Stone mews cottage, walking distance of Helmsley market square and independent shops, Helmsley Castle and Walled Garden close by.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    0

Lavender Cottage ref: CC233020

Helmsley, North York Moors

£0-£624

Your pets are included in this price

The price per pet is £0, the total pet price is £0

Your pets go free at this property

There is no charge to take your pets to this property.

4 star rating
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0