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 34 cottages near Helmsley.

Feather Holme Farm Cottage ref: DC4690

near Helmsley, North York Moors

£326-£517
3 star rating
Feather Holme Farm Cottage
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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

The Stables ref: 27498

Oswaldkirk, near Helmsley, North York Moors

£379-£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

Mill Cottage ref: DC4885

Rievaulx, near Helmsley, North York Moors

£499-£750
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

Bridge House ref: KOG

Helmsley, , North York Moors

£461-£1193
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

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

Ash Lodge ref: W40993

Nawton, near Helmsley, , North York Moors

£335-£675
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

Moorside Cottage ref: UK2032

Ampleforth, near Helmsley , North York Moors

£447-£1024
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

Hunters Cottage ref: 26343

Helmsley, North York Moors

£287-£705
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

Birchglow ref: IYT

Helmsley, near Pickering, , North York Moors

£565-£1487
5 star rating
Adjacent to the renowned Feversham Arms Hotel and Verbena Spa, this holiday property is ideal for exploring coast and moors.
  • Sleeps
    6
  • Number of Pets
    0
  • Bedrooms
    3
  • Bathrooms
    3
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Wren Lodge ref: E5023

Nawton, near Helmsley, , North York Moors

£354-£613
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

Highfield Barn ref: DC4694

Helmsley, North York Moors

£303-£538
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

Robin Lodge ref: E4478

Nawton, near Helmsley, , North York Moors

£331-£613
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

Lavender Cottage ref: CC233020

Helmsley, North York Moors

£352-£607
4 star rating
Charming cottage very close to the centre of Helmsley. Its full of character, tastefully decorated and has a wide range of amenities including riverside walks, shops, tea rooms and amble pubs right on the doorstep.
  • Sleeps
    4
  • Number of Pets
    0
  • Bedrooms
    2
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Pippin Cottage ref: CC233077

Nunnington near Helmsley, North York Moors

£0-£515
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

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