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.

Clematis Cottage ref: CC233018

Helmsley, North York Moors

£332-£562
4 star rating
Clematis Cottage
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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

Swiss Cottage ref: DC5480

Rievaulx near Helmsley, North York Moors

£517-£817
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

The Firs ref: CC233112

Helmsley, North York Moors

£626-£1304
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
    6
  • Number of Pets
    0
  • Bedrooms
    4
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Wren Lodge ref: E5023

Nawton, nr. Helmsley, North York Moors

£303-£596
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

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

Aban Cottage ref: CC232105

Harome near Helmsley, North York Moors

£487-£572
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

Ryecroft ref: CC233019

Nunnington near Helmsley, North York Moors

£462-£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

Colville House ref: 19181

Helmsley, North York Moors

£332-£955
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

Manor Cottage ref: 17303

Old Byland, nr. Helmsley, North York Moors

£332-£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

Pear Tree Cottage ref: DC4438

Kirkbymoorside, North York Moors

£305-£484
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

Ashberry Cottage ref: E1945

Rievaulx, nr. Helmsley, North York Moors

£326-£662
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

Pippin Cottage ref: CC233077

Nunnington near Helmsley, North York Moors

£542-£564
5 star rating
Charming luxury stone cottage in a stunning location, built with the environment in mind
  • Sleeps
    6
  • Number of Pets
    0
  • Bedrooms
    3
  • Bathrooms
    2
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    4

Garden Cottage ref: CC233040

Nawton near Helmsley, North York Moors

£0-£0
0 star rating
Ideally positioned for exploring North York Moors and Coast
  • Sleeps
    2
  • Number of Pets
    2
  • Bedrooms
    1
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    2

Little Garth ref: CC233081

Wombleton near Pickering, York & Vale of York

£372-£572
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

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