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.

Ashberry Cottage ref: E1945

Rievaulx, near Helmsley, Yorkshire, North York Moors

£345-£680

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3 star rating
Ashberry Cottage
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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

Bridge House ref: KOG

Helmsley, North York Moors

£397-£1148

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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

Ryecroft ref: CC233019

Nunnington near Helmsley, North York Moors

£463-£989

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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

Manor Cottage ref: 17303

Old Byland, near Helmsley, North York Moors

£362-£1056

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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

Cliff Stud Cottages - Frankel Cottage ref: UK2308

Helmsley, North York Moors

£451-£451

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4 star rating
Found on a stud farm, Frankel Cottage offers the perfect base to explore Helmsley and the North York Moors National Park.
  • Sleeps
    5
  • Number of Pets
    1
  • Bedrooms
    3
  • Bathrooms
    1
  • Changeover
    FRI
  • Distance from Helmsley (miles)
    0

Swiss Cottage ref: DC5480

Rievaulx, near Helmsley, North York Moors

£580-£895

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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

Mill Cottage ref: DC4885

Rievaulx, near Helmsley, North York Moors

£528-£771

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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

Lavender Cottage ref: CC233020

Helmsley, North York Moors

£379-£710

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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

Pockley Gates Cottage ref: CC232126

near Helmsley, North York Moors

£399-£787

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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

Wren Lodge ref: E5023

Nawton, near Helmsley, , North York Moors

£333-£568

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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

£306-£554

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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

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

Mill House ref: UK2088

Rievaulx, near Helmsley, North York Moors

£589-£1109

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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

Hunters Cottage ref: 26343

Helmsley, North York Moors

£439-£660

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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

Clyde Cottage ref: CC232125

Nawton near Helmsley, North York Moors

£318-£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