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 37 cottages near Helmsley.

Honeysuckle Cottage ref: ISV

Helmsley, York, North York Moors

£444-£971
4 star rating
Honeysuckle Cottage
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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

Feather Holme Farm Cottage ref: DC4690

near Helmsley, North York Moors

£326-£517
3 star rating
Located near a lovely market town and enjoys superb views over countryside and woodland.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

Aban Cottage ref: CC232105

Harome near Helmsley, North York Moors

£0-£535
4 star rating
Aban Cottage has been lovingly refurbished to a high standard and provides idyllic holiday accommodation.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Ash Tree Cottage ref: DC5386

near Kirkbymoorside, North York Moors

£383-£623
4 star rating
Character courtyard cottage with walks direct from the doorstep.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

The Stables ref: 27498

Oswaldkirk, nr. Helmsley, North York Moors

£349-£906
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

Ryecroft ref: CC233019

Nunnington near Helmsley, North York Moors

£445-£917
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

Oak Tree Cottage ref: DC4437

Kirkbymoorside, North York Moors

£394-£632
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

Manor Cottage ref: 17303

Old Byland, nr. Helmsley, North York Moors

£326-£979
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

Clematis Cottage ref: CC233018

Helmsley, North York Moors

£332-£562
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

Pockley Gates Cottage ref: CC232126

near Helmsley, North York Moors

£397-£743
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

Elm Tree Cottage ref: CC232112

Kirkbymoorside, North York Moors

£382-£23036
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

Clyde Cottage ref: CC232125

Nawton near Helmsley, North York Moors

£342-£607
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

Moorside Cottage ref: UK2032

Ampleforth, near Thirsk, North York Moors

£533-£1041
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
    3
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    3

Honeysuckle Cottage ref: 17199

Oswaldkirk, nr. Helmsley, North York Moors

£308-£664
4 star rating
Enjoy views over the Howardian Hills from this comfortable cottage, ideal for a holiday at any time of year.
  • Sleeps
    3
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    3

Little Garth ref: CC233081

Wombleton near Pickering, York & Vale of York

£372-£542
3 star rating
Delightful cottage situated in a pretty village and just a short drive to the coast.
  • Sleeps
    6
  • Number of Pets
    1
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    3