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Helmsley
The charming market town of Helmsley is situated on the edge of the North York Moors National Park and is the perfect place for a cottage break.

The focal point of the town is its square and ancient cross, which is surrounded on all sides by cosy pubs, boutique and speciality shops and restaurants. Every Friday there is a market that sells local produce.

Helmsley has a fascinating history, with many of its building''s dating back to the 17th Century. The town''s dramatic castle sits on a grassy knoll overlooking the town and tells a fascinating story through its medieval, Tudor and Victorian remains, and 100 foot-high tower. The Helmsley Walled Garden lies just below the castle which has been lovingly restored back to its original Victorian beauty.

Access to some of the most beautiful landscapes in Britain is straight from the cottage door; with mile after mile of rolling heather moors and pretty villages that make up the North York Moors National Park; nearby is the expanse of Duncombe Park, one of Yorkshire''s foremost historic houses. Also close by are the impressive Byland Abbey ruins, once one of the greatest monasteries in England and equally as inspiring is Rievaulx Abbey where 12th Century monks once lived and worshipped.

On a warm day why not take a dip in the town''s open air swimming pool or enjoy lunch in one of the local pubs, all former coaching inns, which sit around the square.

To enjoy the area see our selection of Helmsley holiday cottages.
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  • Bilsdale, near Helmsley, Yorkshire
    Bilsdale, near Helmsley, Yorkshire×

    Laskill Grange - Bridge Cottage

    Bilsdale, near Helmsley, Yorkshire

    Bilsdale, near Helmsley, Yorkshire

    2
    1
    1
    1
    Ref: W43184
    Key Features:
    - Hot Tub - Wifi - Car parking on site - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities
    Situated in 70-acre shared grounds, in a sheltered wooded valley, this cottage is ideal for walkers and cyclists. Situated in 70-acre shared grounds, in a sheltered wooded valley, this cottage is ideal for walkers and cyclists.
    Prices from
    8.3 9 reviews
    8.3 9 reviews

    Accommodation at

    Laskill Grange - Foxglove Cottage
    2
    1
    1
    Laskill Grange - Rievaulx Cottage
    2
    1
    1
  • Nawton, near Helmsley, Yorkshire
    Nawton, near Helmsley, Yorkshire×
    Newly Listed
    Highfield Barn

    Highfield Barn

    Nawton, near Helmsley, Yorkshire

    Nawton, near Helmsley, Yorkshire

    2
    1
    1
    0
    Ref: UK2467
    Key Features:
    - Car parking on site - Pub within 1 mile - Detached Property - Woodburning Stove
    Perfect for a couple who want to enjoy a countryside break, this barn conversion is also within easy reach of the Yorkshire coast. Perfect for a couple who want to enjoy a countryside break, this barn conversion is also within easy reach of the Yorkshire coast.
    Prices from
    9.4 7 reviews
    9.4 7 reviews

    Accommodation at

  • Coxwold, near Thirsk, Yorkshire
    Coxwold, near Thirsk, Yorkshire×
    Newly Listed
    School House Cottage

    School House Cottage

    Coxwold, near Thirsk, Yorkshire

    Coxwold, near Thirsk, Yorkshire

    2
    1
    1
    2
    Ref: UK2454
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio - Woodburning Stove
    This cosy cottage for couples is perfectly placed for enjoying the beautiful walks and cycle trails of the Howardian Hills. This cosy cottage for couples is perfectly placed for enjoying the beautiful walks and cycle trails of the Howardian Hills.
    Prices from
    7.8 5 reviews
    7.8 5 reviews

    Accommodation at

  • Bilsdale, near Helmsley, Yorkshire
    Bilsdale, near Helmsley, Yorkshire×

    Laskill Grange - Rievaulx Cottage

    Bilsdale, near Helmsley, Yorkshire

    Bilsdale, near Helmsley, Yorkshire

    2
    1
    1
    1
    Ref: W43185
    Key Features:
    - Hot Tub - Wifi - Car parking on site - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities
    A charming cottage with a shared hot tub, located within the North York Moors National Park and close to Rievaulx Abbey. A charming cottage with a shared hot tub, located within the North York Moors National Park and close to Rievaulx Abbey.
    Prices from
    9 11 reviews
    9 11 reviews

    Accommodation at

    Laskill Grange - Foxglove Cottage
    2
    1
    1
    Laskill Grange - Bridge Cottage
    2
    1
    1
  • Oulston, near Easingwold, Yorkshire
    Oulston, near Easingwold, Yorkshire×

    Close House Cottage

    Oulston, near Easingwold, Yorkshire

    Oulston, near Easingwold, Yorkshire

    2
    1
    1
    1
    Ref: UKC838
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pets go free
    This Victorian cottage is nestled in the beautiful Yorkshire countryside, with spectacular walks from the doorstep. This Victorian cottage is nestled in the beautiful Yorkshire countryside, with spectacular walks from the doorstep.
    Prices from
    9.6 8 reviews
    9.6 8 reviews

    Accommodation at

  • Bilsdale, near Helmsley, Yorkshire
    Bilsdale, near Helmsley, Yorkshire×

    Laskill Grange - Foxglove Cottage

    Bilsdale, near Helmsley, Yorkshire

    Bilsdale, near Helmsley, Yorkshire

    2
    1
    1
    1
    Ref: W43183
    Key Features:
    - Hot Tub - Wifi - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities
    A rural retreat for two, with a shared hot tub, within the North York Moors National Park. A rural retreat for two, with a shared hot tub, within the North York Moors National Park.
    Prices from
    9 1 reviews
    9 1 reviews

    Accommodation at

    Laskill Grange - Bridge Cottage
    2
    1
    1
    Laskill Grange - Rievaulx Cottage
    2
    1
    1
  • Scackleton, near Hovingham, Yorkshire
    Scackleton, near Hovingham, Yorkshire×

    Highfield Barn

    Scackleton, near Hovingham, Yorkshire

    Scackleton, near Hovingham, Yorkshire

    2
    1
    1
    2
    Ref: 24873
    Key Features:
    - Wifi - Car parking on site - Garden / Patio - Rural Location
    Stunning Howardian Hills are the back drop for this apartment, Hovingham and the market town of Helmsley are close by. Stunning Howardian Hills are the back drop for this apartment, Hovingham and the market town of Helmsley are close by.
    Prices from
    8.6 5 reviews
    8.6 5 reviews

    Accommodation at

  • Helmsley, Yorkshire
    Helmsley, Yorkshire×

    Clematis Cottage

    Helmsley, Yorkshire

    Helmsley, Yorkshire

    3
    2
    1
    0
    Ref: CC233018
    Key Features:
    - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio
    Centrally positioned for exploring all attractions in North Yorkshire. Centrally positioned for exploring all attractions in North Yorkshire.
    Prices from
    9.4 11 reviews
    9.4 11 reviews

    Accommodation at

  • Rievaulx near Helmsley
    Rievaulx near Helmsley×

    Ashberry Farm Cottage

    Rievaulx near Helmsley

    Rievaulx near Helmsley

    3
    1
    1
    0
    Ref: DC0455
    Key Features:
    - Car parking on site - Garden / Patio
    Picture postcard location overlooking the duck pond. Picture postcard location overlooking the duck pond.
    Prices from
    8.3 11 reviews
    8.3 11 reviews

    Accommodation at

  • Oswaldkirk, near Helmsley, Yorkshire
    Oswaldkirk, near Helmsley, Yorkshire×

    Honeysuckle Cottage

    Oswaldkirk, near Helmsley, Yorkshire

    Oswaldkirk, near Helmsley, Yorkshire

    3
    2
    1
    1
    Ref: 17199
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Rural Location - Woodburning Stove
    Enjoy views over the Howardian Hills from this comfortable cottage, ideal for a holiday at any time of year. Enjoy views over the Howardian Hills from this comfortable cottage, ideal for a holiday at any time of year.
    Prices from
    9.5 8 reviews
    9.5 8 reviews

    Accommodation at

  • Scawton, near Helmsley, Yorkshire
    Scawton, near Helmsley, Yorkshire×

    Manor Farm Cottage

    Scawton, near Helmsley, Yorkshire

    Scawton, near Helmsley, Yorkshire

    3
    2
    1
    1
    Ref: UK2058
    Key Features:
    - Wifi - Car parking on site - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities - Rural Location
    Commanding spectacular views over open countryside towards the Hambleton Hills this property is just 1½ miles from Rievaulx Abbey and has excellent footpath walks from the door. Commanding spectacular views over open countryside towards the Hambleton Hills this property is just 1½ miles from Rievaulx Abbey and has excellent footpath walks from the door.
    Prices from
    8.4 17 reviews
    8.4 17 reviews

    Accommodation at

  • Chopgate near Stokesley, Yorkshire
    Chopgate near Stokesley, Yorkshire×

    Crossbill Cottage

    Chopgate near Stokesley, Yorkshire

    Chopgate near Stokesley, Yorkshire

    3
    2
    1
    0
    Ref: CC233062
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Garden / Patio
    Exceptional bird life in the area making it perfect for keen bird watchers. Exceptional bird life in the area making it perfect for keen bird watchers.
    Prices from
    9.6 13 reviews
    9.6 13 reviews

    Accommodation at

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