Cottages in Helmsley

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Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 120 cottages

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Map View
An outdoor seating area with a table and two chairs next to a small shed and a covered seating area at Bellwether in Helmsley
24
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A superb, shepherd’s hut situated on the outskirts of the market town of Helmsley. Woodburner. WiFi. Rural views. Kirkbymoorside 3.9 miles; Pickering 10.9 miles. (Ref. 986040)

  • Wi-fi
  • Ground floor bedroom


for 7 nights £305

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A stone building with glass patio doors and a glass balustrade beside a gravel area and wooden fence at Shippon in Beadlam
44
Beadlam, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • 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


for 7 nights £413

Last booked yesterday
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An outdoor scene with gravel driveway trees and a white house with a red roof at Low Grounds Cottage Harome near Helmsley
31
Harome near Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Low Grounds Cottage, a wonderful holiday bungalow resting just outside Harome, North Yorkshire. Woodburning stove. Rural location. Private driveway. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 17.7 miles; York 23.7 miles. (Ref. 1153174)

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


for 7 nights £535

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A front yard with a driveway garage lawn flowers and two brick houses at Field Cottage in Kirkbymoorside
25
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A lovely, two-bedroom cottage resting in Kirkbymoorside, North Yorkshire. Near National Park. Countryside views. Close to amenities. Contemporary. Ground-floor living. Enclosed garden. Helmsley 6.1 miles; Pickering 7.6 miles. (Ref. 1131837)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights £379

Last booked yesterday
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An exterior view of a stone house with two front doors and windows with plants in front at 29 Bondgate in Helmsley
38
Helmsley, North York Moors National Park, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A characterful three 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


for 7 nights £559

Last booked yesterday
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A stone house with a blue door and two chimneys seen from a garden with a stone path and green plants at Cliff House in Helmsley
53
Helmsley, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7★

    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
  • Dishwasher
  • Washing machine


for 7 nights £518

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A garden with a small brick house and a wooden pergola with a table and chairs at Gormire Cottage in Sutton-under-Whitestonecliffe near Thirsk
21
Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A luxury, detached, stone barn conversion in Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire. Woodburning stove. Pool table. Large shared garden. Thirsk 4.6 miles; Northallerton 12.7 miles. (Ref. 1052313)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £425

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A stone cottage with three chimneys and a wooden fence at Lilac Cottage in Wombleton near Beadlam
26
Wombleton near Beadlam, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Lilac Cottage is a delightful cottage nestled in the village of Wombleton in North Yorkshire. Close to farm shop. Near North York Moors. Enclosed garden. Helmsley 4.2 miles; Pickering 10.1 miles; York 22.2 miles (Ref. 1126412)

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

  • 5% off - Fri 6th Mar to 13th Mar 2026


for 7 nights £334

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An exterior view of a stone cottage with a wooden door and windows with warm light at Summerfield Farm Cottage Helmsley
16
Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A charming, stone-built cottage resting on the outskirts of Helmsley. Pet-friendly. WiFi. Woodburning stove. Kirkbymoorside 5.3 miles. (Ref. 1016619)

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


for 7 nights £297

Last booked yesterday
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An outdoor garden with a lodge and seating at Ryedale Country Lodges - Willow Lodge in Kirkbymoorside
23
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A wood-clad lodge resting within the town of Kirkbymoorside. All-ground-floor. Pet-friendly. WiFi. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011653)

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


for 7 nights £479

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A stone cottage with a tiled roof a gravel driveway potted plants and a garden gate at Henhouse Cottage in Gillamoor
16
Gillamoor, North York Moors National Park, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A wonderful stone bungalow located in the village of Gillamoor, North Yorkshire. Open-plan. Woodburner. Open countryside views. Kirkbymoorside 2.7 miles; Pickering 11 miles. (Ref. 984261)

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


for 7 nights £478

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A stone exterior wall of a house with a door and windows and potted plants on a paved patio at Mole End in Wass near Helmsley
19
Wass near Helmsley, North York Moors National Park, YO61
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • 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


for 7 nights £356

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A log cabin with patio furniture and lawn at Ryedale Country Lodges - Hazel Lodge Kirkbymoorside
29
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A superb, detached lodge resting on the outskirts of Kirkbymoorside. All-ground-floor. WiFi. Pet-friendly. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011649)

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


for 7 nights £485

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An outdoor patio area with a glass topped wicker table and wicker chairs with cushions at The Old Dairy in Sutton near Thirsk
31
Sutton near Thirsk, North Yorkshire, YO7
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A charming, two-bedroom barn conversion resting in Sutton near Thirsk, North Yorkshire. Rural. Near National Park. Woodburning stove. Pet-friendly. Contemporary. Ripon 16.4 miles; York 25.2 miles. (Ref. 1134525)

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


for 7 nights £490

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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 £329

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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 £511

Last booked yesterday
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A stone barn with green windows and doors next to a gravel driveway and trees at Woodside Barn in Sutton-under-Whitestonecliffe near Thirsk
26
Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This superb detached, stone barn conversion rests on the outskirts of Thirsk, North Yorkshire. Woodburner. Pet-friendly. Northallerton 12.7 miles. (Ref. 1021256)

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


for 7 nights £463

Last booked 2 days ago
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A large beige house with a tiled roof and multiple windows on a lawn with patio furniture and a hot tub at Tuft House in Hovingham
53
Hovingham, North Yorkshire, YO62
  • Sleeps18
  • Bedrooms9
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This delightful, detached, white stone cottage is situated on the outskirts of Hovingham, North Yorkshire. WiFi. Woodburner. Hot tub. Country views. Helmsley 8 miles; Malton 8 miles. (Ref. 960851)

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


for 7 nights £2701

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A stone cottage with a tiled roof and potted plants outside at Sunset Cottage in Kirkbymoorside
24
Kirkbymoorside, North Yorkshire, YO62
  • 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


for 7 nights £416

Last booked 2 days ago
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The exterior of a two story house with four windows and a blue door at Crumble's Cottage in Kirkbymoorside
18
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A pretty, semi-detached cottage lying in Kirkbymoorside, North Yorkshire. Near a National Park. Woodburning stove. Close to amenities. Helmsley 5.6 miles; Pickering 7.7 miles. (Ref. 1118132)

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


for 7 nights £374

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Map View

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.