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.

Colville House ref: 19181

Helmsley, North York Moors

£288-£976

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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

Ash Lodge ref: W40993

Nawton, near Helmsley, North York Moors

£311-£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

Lavender Cottage ref: CC233020

Helmsley, North York Moors

£379-£686

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4 star rating
This charming cottage is located very close to the centre of Helmsley, with amenities including riverside walks, shops and ample pubs on the doorstep.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Hunters Cottage ref: 26343

Helmsley, North York Moors

£289-£726

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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

Highfield Barn ref: DC4694

Helmsley, North York Moors

£0-£538

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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

Clyde Cottage ref: CC232125

Nawton near Helmsley, North York Moors

£364-£629

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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

Pear Tree Cottage ref: DC4438

Kirkbymoorside, North York Moors

£335-£498

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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

Wren Lodge ref: E5023

Nawton, near Helmsley, , North York Moors

£340-£630

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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

Clematis Cottage ref: CC233018

Helmsley, North York Moors

£354-£584

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4 star rating
Centrally positioned for exploring all attractions in North Yorkshire.
  • Sleeps
    3
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    0

Robin Lodge ref: E4478

Nawton, near Helmsley, , North York Moors

£308-£630

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3 star rating
Peaceful lodge enjoying lovely views, close to Helmsley with castle and market square, Rievaulx Abbey and Castle Howard close by.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Plum Tree Cottage ref: CC232113

Kirkbymoorside, North York Moors

£303-£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

Ashberry Cottage ref: E1945

Rievaulx, near Helmsley, Yorkshire, North York Moors

£336-£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 Stables ref: 27498

Oswaldkirk, near Helmsley, North York Moors

£469-£897

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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

Camomile Cottage ref: 19797

Nunnington, North York Moors

£359-£736

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

Manor Cottage ref: 17303

Old Byland, near Helmsley, North York Moors

£362-£981

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4 star rating
Set within the North York Moors National Park, this detached house is great for walking, cycling and riding.
  • Sleeps
    8
  • Number of Pets
    1
  • Bedrooms
    4
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4