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 33 cottages near Helmsley.

Colville House ref: 19181

Helmsley, North York Moors

£288-£990

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3 star rating
Colville House
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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

Swiss Cottage ref: UK2450

Rievaulx, near Helmsley, North York Moors

£579-£1380

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4 star rating
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

Ash Tree Cottage ref: DC5386

near Kirkbymoorside, North York Moors

£335-£630

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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

Moorside Cottage ref: UK2032

Ampleforth, near Helmsley, North York Moors

£464-£1029

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4 star rating
Moorside Cottage is situated in the heart of the delightful village of Ampleforth, on the edge of the North York Moors National Park and within walking distance of the village pub.
  • Sleeps
    6
  • Number of Pets
    2
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    3

Pear Tree Cottage ref: DC4438

Kirkbymoorside, North York Moors

£285-£511

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

Pockley Gates Cottage ref: CC232126

near Helmsley, North York Moors

£399-£739

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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

Ashberry Farm Cottage ref: DC0455

Rievaulx near Helmsley, North York Moors

£265-£474

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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

Mill Cottage ref: UK2449

Rievaulx, near Helmsley, North York Moors

£673-£1239

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4 star rating
A detached character cottage with an open fire, overlooking Rievaulx Abbey.
  • Sleeps
    5
  • Number of Pets
    2
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Oak Tree Cottage ref: DC4437

Kirkbymoorside, North York Moors

£416-£667

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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

Ash Lodge ref: W40993

Nawton, near Helmsley, North York Moors

£321-£744

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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

The Firs ref: CC233112

Helmsley, North York Moors

£504-£1332

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

Camomile Cottage ref: 19797

Nunnington, North York Moors

£359-£359

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4 star rating
In an idyllic peaceful location, a lovely comfortable cottage from where you can explore this wonderful area.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    4

Wren Lodge ref: E5023

Nawton, near Helmsley, , North York Moors

£311-£681

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3 star rating
Spacious lodge in peaceful countryside, market town of Kirkbymoorside close by, and Scarborough’s sandy beaches and seaside attractions easily reached.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    2

Mill Cottage ref: DC4885

Rievaulx, near Helmsley, North York Moors

£542-£793

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4 star rating
A detached character cottage with an open fire, overlooking Rievaulx Abbey.
  • Sleeps
    5
  • Number of Pets
    2
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Plum Tree Cottage ref: CC232113

Kirkbymoorside, North York Moors

£320-£582

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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