Cottages in Helmsley

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Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 146 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 $417

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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

    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


for 7 nights $559

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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 $663

Last booked yesterday
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A stone and brick house with a garden area containing various plants and shrubs under a blue sky at Auburn House in Beadlam near Helmsley
13
Beadlam near Helmsley, North Yorkshire, YO62
  • 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


for 7 nights $838

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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

    4.9★

    Outstanding

  • 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 $648

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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 $653

Last booked yesterday
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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 $491

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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 $707

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An outdoor patio area with a wicker sofa set and table stone walls and wooden fence at Ford End Cottage in Ampleforth
27
Ampleforth, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A lovely converted carriage house dating back to the 18th century in the village centre of Ampleforth, North York Moors National Park. Underfloor heating. Woodburning stove. Village centre. Helmsley 4.9 miles; Rievaulx 7.5 miles; Kirkham Abbey 17.3 miles. (Ref. 1051110)

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


for 7 nights $791

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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


for 7 nights $452

Last booked yesterday
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A stone cottage with red tile roof and white framed windows next to a small gravel area with a wooden fence and surrounded by greenery at Yon Cottage in Stonegrave near Hovingham
22
Stonegrave near Hovingham, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • 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


for 7 nights $437

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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

    4.9★

    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


for 7 nights $535

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A stone house with five windows two chimneys and a white door with bushes in front at Hill Top in Stonegrave
24
Stonegrave, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This charming semi-detached cottage is situated in the village of Stonegrave, in North Yorkshire. WiFi. En-suite. Woodburner. (Ref. 989054)

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


for 7 nights $659

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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 $437

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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 $666

Last booked yesterday
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Stone exterior of a cottage with a red door four white windows and flower pots at Barn Cottage Marton near Kirkbymoorside
25
Marton near Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

An attractive, mid-terrace barn conversion resting in Marton near Kirkbymoorside, North Yorkshire. Woodburning stove. Pet-friendly. Enclosed garden. Off-road parking. Pickering 4.8 miles; Helmsley 9.1 miles. (Ref. 1081033)

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


for 7 nights $513

Last booked yesterday
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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

    4.9★

    Outstanding

  • 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 $486

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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

    4.6★

    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 $803

Last booked 2 days ago
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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 $606

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A stone building with two green doors and a bench next to a pond with lily pads at The Cottage in Thirsk
25
Thirsk, North York Moors National Park, YO7
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7★

    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


for 7 nights $412

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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.