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)
Sort list by

There are 36 cottages near Helmsley.

Moorside Cottage ref: UK2032

Ampleforth, near Helmsley, North York Moors

£468-£1101

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

4 star rating
Moorside Cottage
Add to favourites Remove from favourites
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

The Stables ref: 27498

Oswaldkirk, near Helmsley, North York Moors

£469-£945

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Hunters Cottage ref: 26343

Helmsley, North York Moors

£343-£691

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

£321-£569

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

0 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

Bridge House ref: KOG

Helmsley, North York Moors

£401-£1318

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

5 star rating
Located in the town of Helmsley, this Grade II listed house is great for visiting Helmsley Castle and Duncombe Park.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    3
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    0

Mill Cottage ref: DC4885

Rievaulx, near Helmsley, North York Moors

£542-£793

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Ash Lodge ref: W40993

Nawton, near Helmsley, North York Moors

£329-£744

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Clematis Cottage ref: CC233018

Helmsley, North York Moors

£354-£609

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Ashberry Cottage ref: E1945

Rievaulx, near Helmsley, Yorkshire, North York Moors

£345-£667

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Swiss Cottage ref: DC5480

Rievaulx, near Helmsley, North York Moors

£596-£920

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Plum Tree Cottage ref: CC232113

Kirkbymoorside, North York Moors

£336-£582

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Finch Lodge ref: E4793

Nawton, near Helmsley, , North York Moors

£266-£681

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

3 star rating
Cosy lodge with decking and country views, close to Camp Eden, York with Minster and Jorvik Viking Centre easily reached.
  • Sleeps
    4
  • Number of Pets
    1
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    SAT
  • Distance from Helmsley (miles)
    2

Oak Tree Cottage ref: DC4437

Kirkbymoorside, North York Moors

£416-£667

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Feather Holme Farm Cottage ref: DC4690

near Helmsley, North York Moors

£345-£546

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

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

Mill House ref: UK2088

Rievaulx, near Helmsley, North York Moors

£669-£1630

searchresult-paid-pet-description

searchresult-paid-pet-tooltip

searchresult-free-pet-description

searchresult-free-pet-tooltip

4 star rating
A Grade II listed detached cottage with an open fire, set in an idyllic picturesque valley alongside the magnificent ruins of Rievaulx Abbey - a warm welcoming ambience is assured.
  • Sleeps
    5
  • Number of Pets
    2
  • Bedrooms
    3
  • Bathrooms
    2
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    2