Cottages in Helmsley

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Cottages in Helmsley

Your Helmsley, North Yorkshire search returned 120 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 stone building with glass patio doors and a glass balustrade beside a gravel area and wooden fence at Shippon in Beadlam
1 of 44
5
Beadlam, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £413

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An outdoor seating area with a table and two chairs next to a small shed and a covered seating area at Bellwether in Helmsley
1 of 24
5
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £305

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A house with a garden and planters at Low Grounds Cottage in Harome near Helmsley
1 of 30
5
Harome near Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £535

Last booked 2 days ago
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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
1 of 53
5
Helmsley, Yorkshire Dales - North, YO62
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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 From £518

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
1 of 25
5
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From £376

Last booked yesterday
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A wooden shepherds hut with an open door behind a wooden gate and stone wall with chairs and table on grass at Sheep Cote Shepherds Hut in Chop Gate near Stokesley
1 of 27
5
Chop Gate near Stokesley, North York Moors National Park, TS9
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

A gorgeous, one-bed hut sitting in a rural location in Chop Gate, near Stokesley, North Yorkshire. Countryside location. Ideal for couples. Rural views. Great Ayton 10.4 miles; Saltburn-by-the-Sea 20.2 miles. (Ref. 1126877)

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


for 7 nights From £462

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
1 of 13
5
Beadlam near Helmsley, North Yorkshire, YO62
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    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 From £648

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
1 of 22
5
Stonegrave near Hovingham, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £323

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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
1 of 38
5
Helmsley, North York Moors National Park, YO62
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £583

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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
1 of 21
5
Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From £425

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A log cabin with patio furniture and lawn at Ryedale Country Lodges - Hazel Lodge Kirkbymoorside
1 of 29
5
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From £479

Last booked 2 days ago
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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
1 of 27
5
Ampleforth, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £580

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An outdoor garden with a lodge and seating at Ryedale Country Lodges - Willow Lodge in Kirkbymoorside
1 of 23
5
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From £435

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A stone cottage with three chimneys and a wooden fence at Lilac Cottage in Wombleton near Beadlam
Offer
1 of 26
5
Wombleton near Beadlam, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

  • 10% off - Fri 24th Jul to 31st Jul 2026


for 7 nights From £334

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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
1 of 24
5
Stonegrave, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £501

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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
1 of 16
5
Gillamoor, North York Moors National Park, YO62
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £463

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A stone cottage with a red tiled roof and manicured garden at Ivy Cottage in Helmsley
1 of 24
5
Helmsley, North York Moors National Park, YO62
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.6★

    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 From £491

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
1 of 26
5
Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire, YO7
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    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 From £463

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A wooden cabin with a porch, two chairs, a small table, and a grassy lawn at Rising Sun in Kirkbymoorside
1 of 22
5
Kirkbymoorside, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0★

    Perfect

  • 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 From £642

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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
1 of 31
5
Sutton near Thirsk, North Yorkshire, YO7
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • 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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom


for 7 nights From £582

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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.