Cottages in Helmsley

Your Helmsley, North Yorkshire search returned 118 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A two-story brick house with a garage and driveway next to a grassy area and trees at Temple Hill View in Ampleforth
19
Ampleforth, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Temple Hill View, a friendly abode in the village of Ampleforth in North Yorkshire. Off-road parking. Near shop. Enclosed garden. Countryside views. Helmsley 5.1 miles; York 19.3 miles; Scarborough 35.6 miles. (Ref. 1159134)

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


for 7 nights $764

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A garden with wooden table and chairs and plants in front of a stone house with large windows at The Granary in Appleton-le-Moors
19
Appleton-le-Moors, North York Moors & Coast, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

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)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $602

Last booked 3 hours ago
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A gravel path leading to a small building with ivy-covered walls and a tiled roof surrounded by various green bushes and white flowering plants at The Hayloft in Lastingham
19
Lastingham, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Charming detached stone-built barn conversion in picturesque Lastingham. Quality accommodation with woodburning stove. Excellent walking, coast easily accessible. Pickering 7 miles. (Ref. 1571)

  • Wi-fi
  • Off-road parking


for 7 nights $484

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A stone cottage with a tiled roof surrounded by bushes and flowers with a wooden door and two windows at Rose Cottage in Kirkbymoorside
18
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A characterful barn conversion resting on a working farm near the town of Kirkbymoorside. TV with Freeview. Countryside views. Near North York Moors National Park. Dog-friendly. (Ref. 974385)

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


for 7 nights $447

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A stone house with a garden and picnic table at Wethercote Cottage Old Byland near Helmsley
Offer
25
Old Byland near Helmsley, North York Moors National Park, YO7
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Tourist Board 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

  • 10% off - Fri 29th May to 19th Jun 2026


for 7 nights $477

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A stone cottage with a tiled roof and metal railing in a rural setting at Beckside in Lastingham
18
Lastingham, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

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)

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


for 7 nights $448

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A living room with a wood burning stove and wooden staircase at 5 Rosedale Abbey in Rosedale Abbey
30
Rosedale Abbey, North York Moors National Park, YO18
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A pretty cottage nestled in the picturesque village of Rosedale, North Yorkshire. Woodburning stove. Garden. Dishwasher. Kirkbymoorside 7.9 miles; Pickering 10.3 miles. (Ref. 1102061)

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


for 7 nights $796

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Front view of a stone house with blue doors and tiled roof surrounded by trees and bushes at Howe Green Cottage in Kirkbymoorside
14
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Exceedingly pretty, detached stone cottage, a short walk from centre of Kirkbymoorside. Beamed ceilings, open fire. National Park and Heritage Coast within easy driving distance. Pickering 6 miles. (Ref. 1034138)

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


for 7 nights $556

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An outdoor area with a stone building with tiled roof multiple white doors and windows a raised stone patio with potted plants chairs and a bench on gravel at Norah's Nook in Farndale near Kirkbymoorside
18
Farndale near Kirkbymoorside, North York Moors National Park, YO62
  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.8★

    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


for 7 nights $425

Last booked 2 days ago
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A stone cottage with a red tiled roof and manicured garden at Ivy Cottage in Helmsley
24
Helmsley, North York Moors National Park, YO62
  • 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


for 7 nights $669

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A house with a garden and driveway at 17 Costa Way in Pickering
21
Pickering, North Yorkshire, YO18
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A well-equipped bungalow situated in the market town of Pickering, Yorkshire. Ideal for families. Touring location. Kirkbymoorside 6.6 miles; Helmsley 12.1 miles. (Ref. 1070204)

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


for 7 nights $675

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A stone cottage with two green doors and white framed windows at Bay Tree Cottage in Pickering
26
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Bay Tree Cottage is a delightful terraced cottage resting in Pickering, North Yorkshire. Near National Park. Woodburning stove. Close to shop and pub. Kirkby Misperton 4.4 miles; Malton 8.8 miles. (Ref. 1115722)

  • Wi-fi
  • Dishwasher


for 7 nights $610

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Row of brick terraced houses with different colored front doors along a street with grass verge at Cloverleaf Cottage in Pickering
18
Pickering, North Yorkshire, YO18
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A delightful mid-terrace cottage resting within the market town of Pickering. Woodburning fire. Fibre Optic WiFi. Pub within 0.2 miles. Scarborough 18 miles; Whitby 22 miles. (Ref. 1003948)

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


for 7 nights $597

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Exterior of a stone and wood building with a tiled roof and skylights and a round wooden picnic table with an umbrella in front at The Granary in Sutton-Under-Whitestonecliffe near Thirsk
19
Sutton-Under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A delightful three bed barn conversion on a small complex, in peaceful location on the edge of the village of Sutton-Under-Whitestonecliffe. Open plan living area, galleried landing. Ideal walking area. Thirsk 4 miles. (Ref. 19935)

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


for 7 nights $675

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A living area with a sofa and coffee table adjacent to a kitchen with white cabinets and a wooden door at Crumble's Hideaway in Kirkbymoorside
14
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This delightful cottage resides in Kirkbymoorside, North Yorkshire. Close to amenities. Couples’ getaway. En-suite bathroom. Smart TV. Pickering 7.7 miles; Helmsley 5.6 miles. (Ref. 963205)

  • Wi-fi
  • Dishwasher


for 7 nights $505

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A dining area with a wooden table and chairs beside a living room with sofas a tv and a window seat at Potter Hill Cottage in Pickering
25
Pickering, North Yorkshire, YO18
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

This inviting mid-terrace sits at the centre of Pickering in North Yorkshire, on the fringes of the North York Moors National Park. Three-storey. Pet-friendly. Amenities in walking distance. Malton 8.7 miles; Scarborough 18.2 miles; York 26.8 miles. (Ref. 1025071)

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


for 7 nights $537

Last booked 3 hours ago
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Exterior view of a wooden lodge with a deck and garden area with flowers and a parked car at 3 Valley View Lodges Nawton near Helmsley
15
Nawton near Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

3 Valley View Lodges is a detached, single-storey lodge resting in Nawton near Helmsley, North Yorkshire, boasting an electric fire and rural views. Kirkbymoorside 3.1 miles; Pickering 10.5; Thirsk 17 miles; York 24 miles. (Ref. 1077224)

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


for 7 nights $496

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A stone cottage with wooden shutters and a small outdoor seating area at Cow Byre Cottage in Wrelton near Pickering
10
Wrelton near Pickering, North Yorkshire, YO18
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Delightful conversion of old cow byre in centre of Wrelton. Exposed timbers, wooden floors. Quality cottage, very high standard. Excellent walking and touring base. Pickering 3 miles. (Ref. 1577)

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


for 7 nights $391

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A stone house with a tiled roof a wooden bench and potted plants on a gravel path with a grassy lawn in front at The Burrows in Wass near Helmsley
24
Wass near Helmsley, North York Moors National Park, YO61
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Burrows, a charming holiday cottage located in the quaint town of Helmsley, North Yorkshire. Woodburning stove. Enclosed garden. In North York Moors.Helmsley 6.4 miles; York 21.3 miles; Scarborough 38 miles. (Ref. 1150998)

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


for 7 nights $689

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Stone cottage facade with three doors and multiple windows on the front at Crooked Cottage in Kirkbymoorside
24
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    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


for 7 nights $549

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