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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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  • Customers'
    choice award

    Poppy Cottage

    Helmsley, Yorkshire

    14/05/2019
    9.9 22 reviews
    9.9 22 reviews
    Ref: IZL
    Luxury Wifi Enclosed Garden / Patio Pub within 1 mile Garden / Patio Open Fire
    4
    2
    2
    0
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  • Customers'
    choice award

    Laskill Grange - Rievaulx Cottage

    Bilsdale, near Helmsley, Yorkshire

    8.6 8 reviews
    8.6 8 reviews
    Ref: W43185
    Hot Tub Wifi Car parking on site Pets go free Detached Garden / Patio Ground Floor Facilities
    2
    1
    1
    1
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    Accommodation at

    Laskill Grange - Foxglove Cottage
    2
    1
    1
    Laskill Grange - Bridge Cottage
    2
    1
    1
  • Customers'
    choice award

    Laskill Grange - Bridge Cottage

    Bilsdale, near Helmsley, Yorkshire

    7.4 5 reviews
    7.4 5 reviews
    Ref: W43184
    Hot Tub Wifi Car parking on site Pets go free Detached Garden / Patio Ground Floor Facilities
    2
    1
    1
    1
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    Accommodation at

    Laskill Grange - Foxglove Cottage
    2
    1
    1
    Laskill Grange - Rievaulx Cottage
    2
    1
    1
  • Customers'
    choice award

    Close House Cottage

    Oulston, near Easingwold, Yorkshire

    14/05/2019
    10 2 reviews
    10 2 reviews
    Ref: UKC838
    Wifi Car parking on site Enclosed Garden / Patio Pets go free
    2
    1
    1
    1
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  • Customers'
    choice award

    School House Cottage

    Coxwold, near Thirsk, Yorkshire

    7.9 9 reviews
    7.9 9 reviews
    Ref: UK2454
    Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free Garden / Patio Woodburning Stove
    2
    1
    1
    2
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    Accommodation at

  • Customers'
    choice award

    Laskill Grange - Foxglove Cottage

    Bilsdale, near Helmsley, Yorkshire

    9 3 reviews
    9 3 reviews
    Ref: W43183
    Hot Tub Wifi Pets go free Detached Garden / Patio Ground Floor Facilities
    2
    1
    1
    1
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    Accommodation at

    Laskill Grange - Bridge Cottage
    2
    1
    1
    Laskill Grange - Rievaulx Cottage
    2
    1
    1
  • Customers'
    choice award

    Highfield Barn

    Scackleton, near Hovingham, Yorkshire

    8.9 7 reviews
    8.9 7 reviews
    Ref: 24873
    Wifi Car parking on site Garden / Patio Rural Location
    2
    1
    1
    2
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  • Customers'
    choice award

    Highfield Barn

    Nawton, near Helmsley, Yorkshire

    9.7 23 reviews
    9.7 23 reviews
    Ref: UK2467
    Car parking on site Pub within 1 mile Detached Woodburning Stove
    2
    1
    1
    0
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  • Customers'
    choice award

    Ashberry Farm Cottage

    Rievaulx near Helmsley

    8.5 10 reviews
    8.5 10 reviews
    Ref: DC0455
    Car parking on site Garden / Patio
    3
    1
    1
    0
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  • Customers'
    choice award

    Honeysuckle Cottage

    Oswaldkirk, near Helmsley, Yorkshire

    14/05/2019
    9.4 8 reviews
    9.4 8 reviews
    Ref: 17199
    Wifi Car parking on site Pub within 1 mile Pets go free Rural Location Woodburning Stove
    3
    2
    1
    1
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    Accommodation at

  • Customers'
    choice award

    Crossbill Cottage

    Chopgate near Stokesley, Yorkshire

    9.7 6 reviews
    9.7 6 reviews
    Ref: CC233062
    Wifi Car parking on site Enclosed Garden / Patio Garden / Patio
    3
    2
    1
    0
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  • Customers'
    choice award

    Manor Farm Cottage

    Scawton, near Helmsley, Yorkshire