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Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 122 cottages

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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Lovely double-fronted cottage within a short stroll of the picturesque market town of Helmsley within the North Yorkshire National Park. WiFi. Lawned garden. Walks from the door. Kirkbymoorside 6 miles. (Ref. 947064)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £442

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

This quaint cottage lies in the market town, Hemlsley, North Yorkshire. Original features. WiFi. Off-road parking. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 14.3 miles; York 24.8 miles. (Ref. 1064092)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £554

Last booked 6 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A characterful two-bedroom holiday cottage settled in Helmsley, in North Yorkshire. Garden. Pet-friendly. Washing machine. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 14 miles; York 24.1 miles. (Ref. 1089307)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £647

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful, semi-detached bungalow resting in the pretty village of Harome in North Yorkshire. Ideal for two couples. Enclosed lawned garden. Helmsley 3 miles; Pickering 11.6 miles. (Ref. 1044119)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £505

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Magnificent semi-detached property in market town of Helmsley. Beautifully presented and well-equipped. Open fire, conservatory, delightful garden. Close to all amenities. (Ref. 2779)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £782

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A romantic, single-storey cottage resting in Beadlam, North Yorkshire. Open-plan. Beautiful views. Helmsley 2.2 miles; Pickering 10.9 miles; York 24.4 miles. (Ref. 1099725)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £402

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

Mole End is a lovely, single-storey cottage located in the charming market town of Helmsley, North Yorkshire. Woodburning stove. Couple's retreat. Kirkbymoorside 13.2 miles; Thirsk 12.8 miles; Pickering 20.3 miles; York 22 miles. (Ref. 1151091)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from £349

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

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)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £655

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Detached pet-friendly cottage near Hovingham. Single-storey cottage, rural position on arable farm estate, underfloor heating. Well equipped and comfortable. Close to Nunnington, Castle Howard, pretty market towns. Hovingham 3 miles. (Ref. 21723)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £293

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Cosy, ground floor cottage placed near the North Yorkshire town of Kirkbymoorside. Open-plan living. Exposed wooden beams. En-suites. Near North York Moors National Park. (Ref. 974388)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £393

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Detached attractive stone barn conversion in a peaceful location near Kirkbymoorside. Single-storey accommodation with exceptional countryside views and superb walking opportunities. Kirkbymoorside 2.5 miles. (Ref. 911836)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £339

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A stone-built cottage which rests on the outskirts of Thirsk, North Yorkshire. Open-plan. WiFi. Just a moment’s walk from the Cleveland National Trail. York 27 miles. (Ref. 1004365)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £324

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Detached stone barn conversion in courtyard setting on owners' farm, near Kirkbymoorside. Single-storey accommodation, with a comfortable open plan living area and pretty bedroom. Easy access to North York Moors National Park. Kirkbymoorside 2.5 miles. (Ref. 929845)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £339

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A charming stone-fronted cottage resting in Ampleforth, North Yorkshire. Original features. In North York Moors National Park. Close to amenities. Woodburning stove. Helmsley 4.9 miles; York 19.4 miles; Scarborough 35.4 miles. (Ref. 1115609)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £990

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming, Grade II listed cottage on the edge of pretty Kirkbymoorside, Yorkshire. Pickering 6 miles. Close to North York Moors National Park. (Ref. 985142)

  • Wi-fi
  • Washing machine

7 nights from £384

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A wonderful, semi-detached cottage settled in Stonegrave near Hovingham, North Yorkshire. Woodburning stove. Near National Park. Romantic. Helmsley 5.9 miles; Malton 10.1 miles; York 18.5 miles. (Ref. 1106690)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £344

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

One of our farm based Yorkshire cottages, with lovely views over the moors, 7 miles from the market town of Helmsley. (Ref. 3626)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £354

  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

Harwood Cottage, a stunningly-presented holiday home in the charming village of Hovingham. Streamside. Garden with barbecue. Conservatory. Child-friendly. Helmsley 7.9 miles; Malton 8.2 miles; York 17.3 miles. (Ref. 1155772)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £421

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Beautiful stone cottage in the North York Moors National Park, close to the village of Hutton-le-Hole. Exposed beams. Surrounded by countryside. Hutton-le-Hole 1.5 miles. (Ref. 975266)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £334

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Hobbits is a fabulous detached barn conversion offering flexible accommodation and beautifully positioned in the glorious Howardian Hills near York and Malton. York 12 miles. (Ref. 20946)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £373

On the border of the North York Moors National Park, this delightful market town is a haven for walkers and lovers of the outdoors.

Why Helmsley?

After an action-packed day among the wonders of the North York Moors, our Helmsley cottages enjoy close proximity to the town's charming pubs and delightful tea rooms to recharge the batteries. There is a selection of excellent independent shops and a weekly market along its attractive streets to pick up some of the finest local produce. From your Helmsley accommodation, be sure to explore the stunning Helmsley Castle and sculpture garden, as well as Duncombe Park and the National Centre for Birds of Prey for nature enthusiasts.

Places to Visit near Helmsley

Our range of cottages in Helmsley rest on the southern fringes of the North York Moors National Park, perfectly based for a break filled with activity and adventure. This National Park hugging the coast of Yorkshire has much to offer, not least its wide range of walks and cycle paths taking in some of the finest landscape scenery imaginable. Discover a handful of unique villages in and around the spectacular moors, waiting to be explored with rustic inns and delightful cafés offering those mid-adventure refreshments. Make your Helmsley cottage holiday a memorable one by visiting popular spots such as Ampleforth, Hutton-le-Hole, Kirkbymoorside, Pickering, Ripon and Thirsk.

Types of Holidays

All types of holidays can be enjoyed across Yorkshire with Sykes, whether you're seeking a Yorkshire cottage by the sea, or more of a rural retreat at a cottage in the Yorkshire countryside. Bring your dog along to enjoy the sublime walking country nearby by booking a North York Moors pet-friendly cottage, or really treat yourselves to a break in a Yorkshire luxury cottage.