Cottages in Helmsley

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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
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 €354

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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
29
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 €621

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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 €479

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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

    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


for 7 nights €375

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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 €440

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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, Yorkshire Dales - North, 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 €601

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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 €751

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

    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 €413

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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 €345

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A stone house with a tiled roof and a small garden with a table and two chairs at 8 Pottergate Mews in Helmsley
27
Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Ideal for a family holiday in the heart of market town. Front garden and rear courtyard. WiFi. Thirsk 14 miles. (Ref. 956799)

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


for 7 nights €649

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A stone cottage with three chimneys and a wooden fence at Lilac Cottage in Wombleton near Beadlam
Offer
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

  • 10% off - Mon 1st Jun to 30th Jun 2026


for 7 nights €388

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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 €493

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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 €563

Last booked yesterday
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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

    5.0★

    Perfect

  • 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 €671

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A wooden cabin with a porch, two chairs, a small table, and a grassy lawn at Rising Sun in Kirkbymoorside
22
Kirkbymoorside, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A lovely one-bedroom lodge perched near Kirkbymoorside, North Yorkshire. Pet-free. Wood fired hot tub. Near National Park. Romantic. Pickering 5.8 miles; Helmsley 7.3 miles. (Ref. 1049218)

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


for 7 nights €744

Last booked yesterday
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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 €555

Last booked 3 days ago
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The exterior of a stone cottage with a tiled roof a purple door a small outdoor table and two chairs surrounded by plants and gravel at Pheasant Cottage Low Hagg Farm near Kirkbymoorside
23
Low Hagg Farm near Kirkbymoorside, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Superb barn conversion in open countryside 1.5 miles from Kirkbymoorside. Beams, exposed stone work, woodburning stove. Pickering 6 miles. (Ref. 929317)

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


for 7 nights €737

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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 €440

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A stone cottage with two pale purple doors a gravel courtyard with metal table and chairs and plants at Partridge Cottage Low Hagg Farm near Kirkbymoorside
18
Low Hagg Farm near Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Cosy character cottage in wonderful rural position. All ground floor with disability rating. Views over open countryside. Kirkbymoorside 1.5 miles; Pickering 6 miles. (Ref. 929318)

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


for 7 nights €661

Last booked 3 days ago
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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 €556

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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, 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.