All cottages available for only £20 Deposit!*

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Cottages in Helmsley

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    • Sleeps4
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    Grade II listed, semi-detached, former coaching inn, near centre of Wrelton village. Full of character, exposed beams and woodburning stove. Pickering 3 miles. (Ref. 1844)

    Last booked yesterday

    7 nights from £239

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    Delightful detached stone cottage on owner's complex in Appleton-le-Moors village. Cosy, characterful accommodation with open fire, garden room, fine views over open countryside. Wonderful walking/cycling from the door. Kirkbymoorside 3.5 miles. (Ref. 936454)

    Last booked yesterday

    7 nights from £332

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    Welcoming, single-storey cottage near Rosedale Abbey. Flexible sleeping arrangements, woodburner, superb views. Great touring base. Kirkbymoorside 5 miles. (Ref. 8636)

    Last booked yesterday

    7 nights from £337

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    • Sleeps8
    • Bedrooms4
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    Beautiful period property in village location. Ensuite bathroom. TV with Freeview. Lovely garden. Ample off road parking. Village location with pub and restaurant. Helmsley 3 miles. (Ref. 943848)

    Last booked yesterday

    7 nights from £467

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    • Bedrooms1
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    A single-storey barn conversion in courtyard setting on the outskirts of the small village of Sutton-Under-Whitestonecliffe. Romantic retreat. Open plan living area. Superb area for walking and touring. Thirsk 4 miles. (Ref. 14936)

    Last booked within the last 2 days

    7 nights from £240

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    Detached stone built stable conversion in pretty Lastingham village. Quality ground floor accommodation, streamside patio. Ideal for York Moors & Coast. Pickering 7 miles. (Ref. 1293)

    7 nights from £292

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    Wonderful, semi-detached, barn conversion near Thirsk. Eco-friendly central heating. WiFi. Open plan living area. Ideal touring location. Thirsk 4 miles. (Ref. 15032)

    Last booked within the last 2 days

    7 nights from £305

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    Charming stone cottage in the centre of Helmsley, North Yorkshire. All ground floor. Wet room. Pretty courtyard garden. Quietly tucked away, yet with plenty of amenities on the doorstep. Pickering 14 miles. (Ref. 26954)

    Last booked 4 hours ago

    7 nights from £300

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    A charming barn conversion located near the village of Thirsk, North Yorkshire. Breakfast bar. Open-plan. High ceilings. Ripon 11 miles; York 23 miles. (Ref. 19934)

    7 nights from £230

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Quality, stone, detached barn conversion in rural village near York. Ground floor accommodation. Woodburner. Underfloor heating. WiFi. Excellent walking and cycling base. York 14 miles. (Ref. 25755)

    7 nights from £465

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All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

*Applicable to holidays commencing at least 6 weeks in the future. Full balance due 6 weeks prior to departure. Please refer to Book Now Pay Later Terms and Conditions for further information.

Just show me Helmsley Cottages

Please find below a selection of self catering holiday cottages to rent in Helmsley, Yorkshire.

On the borders of the North York Moors National Park, this lovely little market town is a haven for walkers as it's the starting point of the Ebor Way, a long distance trail that connects the Cleveland Way and Dales Way.

Of course, the National Park is a playground for all kinds of other outdoor activities too like cycling, horse riding, fishing and golf. Plus it's only a short distance from our Helmsley cottages to the coast if you fancy a day on the beach.

Fresh air and exercise create healthy appetites and Helmsley's pubs, tearooms and restaurants are extremely inviting - worth a mention is the Black Swan for fine food amid swish surroundings. There are also stylish shops selling everything from gifts and crafts to country wear, along with a weekly street market.

Attractions include the beautiful Parish Church, a thriving Arts Centre and Helmsley Castle, a magnificent ruined Norman keep overlooking the town, with displays of archaeological treasures and a fascinating interactive exhibition. In the shadow of the castle, just a short distance from the town centre, lies the estate of Duncombe Park and its National Nature Reserve. Spend a day here admiring ancient trees and colourful birdlife and look out for the five-acre Helmsley Walled Garden, a working kitchen garden brimming with special collections of Yorkshire apple trees, Victorian vines and numerous varieties of clematis.

And don't miss a trip to Rievaulx Abbey, an amazing Gothic ruin just a couple of miles away; or Nunnington Hall, a stunning 17th Century manor house.

Sounds appealing? Then book a Helmsley cottage.