Helmsley Cottages

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    • Sykes Rating
    • Sleeps2
    • Bedrooms1
    • PetsNo

    Pretty stone-built cottage in heart of Rosedale Abbey village in North York Moors National Park. Spacious open plan living area, well-equipped kitchen, tastefully furnished. WiFi. Superb walking and touring area. Kirbymoorside 7 miles. (Ref. 936971)

    7 nights from £307

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Pretty, detached, ground floor stone cottage in a small hamlet near Helmsley. Cosy, characterful accommodation for couples. WiFi. Pretty garden. Superb walking country. Helmsley 2 miles. (Ref. 917006)

    Last booked yesterday

    7 nights from £278

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Delightful, stone built cottage in Cropton village in North York Moors. Cosy, comfortable accommodation for couples. Woodburning stove. Surrounded by stunning scenery. Ideal walking country. Pickering 4 miles. (Ref. 10354)

    Last booked within the last 2 days

    7 nights from £294

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Charming and characterful cosy stone cottage for couples, in Slingsby village near Malton. Flagged floors, woodburner, beams, off road parking. High standard throughout. Excellent walking, cycling and touring area. Short drive to York. (Ref. 934754)

    Last booked yesterday

    7 nights from £294

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    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)

    7 nights from £298

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Cosy stone barn conversion in rural countryside between Helmsley and Stokesley. All ground floor, open plan living, one double bedroom. WiFi. Pet-friendly. Superb walking, cycling and touring area. Helmsley 10 miles. (Ref. 931157)

    Last booked 8 hours ago

    7 nights from £287

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Hobbits is a fabulous detached barn conversion offering flexible accommodation and beautifully positioned in the glorious Howardian Hills near York and Malton. York 12 miles. (Ref. 20946)

    7 nights from £289

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Quality, stone, detached barn conversion in rural village near York. Ground floor accommodation. Woodburner. Underfloor heating. WiFi. Excellent walking and cycling base. York 14 miles. (Ref. 25755)

    Last booked yesterday

    7 nights from £488

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Beautiful, first floor, studio-style cottage in rural location. Close to Easingwold and Crayke. Tastefully furnished to high standard. Woodburner, splendid views. Easy access to York. Easingwold 2 miles. (Ref. 917511)

    7 nights from £260

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Wooden chalet on small picturesque complex in rural retreat. Comfortable, open plan accommodation. Beautiful walking area and all outdoor activities. Pet-friendly. Helmsley 5 miles. (Ref. 903688)

    7 nights from £219

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Fabulous stone barn conversion in rural Farndale. Spectacular views, mezzanine bedroom, contemporary furnishings. Ideal romantic retreat. Excellent walking, touring area. Kirkbymoorside 9 miles. (Ref. 911810)

    7 nights from £265

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Modern terraced cottage near centre of Helmsley, North Yorkshire. Secure gated mews property in quiet corner, a short walk to all amenities. WiFi. Pickering 14 miles (Ref. 933163)

    7 nights from £351

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    The largest of three barn conversions set on a working farm in the hamlet of Chop Gate. Original features with exposed beams and stone walls. Woodburner. WiFi. Helmsley 10 miles. (Ref. 938384)

    Last booked yesterday

    7 nights from £366

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    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)

    7 nights from £315

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Charming stone grade II listed cottage in pretty village of Cropton. Original beams and two woodburning stoves. Comfortable, traditional accommodation. Excellent walking area. Pickering 4 miles. (Ref. 12165)

    7 nights from £358

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Stunning stone barn conversion in heart of North York Moors. All ground floor, open plan living, woodburner, granite work tops, underfloor heating. Excellent walking and cycling from the door. Helmsley 10 miles. (Ref. 931158)

    7 nights from £359

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Charming stone cottage in the centre of Helmsley, North Yorkshire. All ground floor. Wet room. Pretty courtyard garden. Quietly tucked away, yet with plenty of amenities on the doorstep. Pickering 14 miles. (Ref. 26954)

    7 nights from £299

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Immaculately-presented, single-storey stone barn conversion in small hamlet of Stearsby near York. Woodburning stove. Countryside views, close to pretty market towns of Helmsley, Easingwold. York 14 miles. (Ref. 8634)

    Last booked within the last 2 days

    7 nights from £358

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Delightful, detached stone barn conversion on edge of Nawton village. 'Upside down' accommodation, character beams. Excellent walking. Helmsley and Kirkbymoorside 4 miles. (Ref. 2688)

    Last booked yesterday

    7 nights from £238

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Single-storey stone barn conversion set on owner's working farm, between Thirsk and Easingwold. Spacious open plan living area, woodburner. Two bedrooms, two bathrooms. High standard throughout. Excellent walking, cycling, touring. Easingwold 5 miles. (Ref. 930756)

    Last booked within the last 2 days

    7 nights from £348

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    Magnificent semi-detached barn conversion in Farndale. Full of character and charm, exposed beams and open fire. Excellent walking from the doorstep. Kirkbymoorside 10 miles. (Ref. 1391)

    Last booked within the last 2 days

    7 nights from £331

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    • Sleeps15
    • Bedrooms7
    • PetsNo

    A luxury, stone-built holiday home in a hamlet location, two miles from Hovingham. Six bedrooms, two woodburners, WiFi. Hot tub. Ideal for families. Helmsley 7 miles. (Ref. 950092)

    7 nights from £1599

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    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. 1785)

    7 nights from £324

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    • Sleeps5
    • Bedrooms3
    • PetsYes

    Spacious and comfortable semi-detached cottage in quiet village of Nawton, on edge of North York Moors. Private rear garden with pleasant aspect. Bike storage. Excellent walking, cycling area. Kirkbymoorside 3 miles. (Ref. 924810)

    Last booked yesterday

    7 nights from £320

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Cosy, stone-built semi-detached cottage in pretty Hovingham. Open fire, sunny garden. Tastefully furnished and decorated. Very comfortable. Malton 8 miles. (Ref. 2661)

    7 nights from £285

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Superb, detached stone property in Kilburn village near Thirsk. Spacious rooms with sunny conservatory. Beautiful lawned garden. Modernised to high standard. Wonderful walking and cycling. Thirsk 6.5 miles. (Ref. 904895)

    7 nights from £399

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    • Sleeps5
    • Bedrooms3
    • PetsNo

    Unique Grade II listed Old School House above shop overlooking village green in Hutton-le-Hole. First floor apartment with character window and enclosed rear courtyard. Modern open plan living. Helmsley 9 miles. (Ref. 932240)

    Last booked yesterday

    7 nights from £300

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Welcoming, single-storey cottage near Rosedale Abbey. Flexible sleeping arrangements, woodburner, superb views. Great touring base. Kirkbymoorside 5 miles. (Ref. 8636)

    7 nights from £328

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    • Sleeps11
    • Bedrooms4
    • PetsYes

    Magnificent semi-detached property in market town of Helmsley. Beautifully presented and well-equipped. Open fire, conservatory, delightful garden. Close to all amenities. (Ref. 2779)

    7 nights from £569

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    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)

    Last booked yesterday

    7 nights from £311

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    • Sykes Rating
    • Sleeps5
    • Bedrooms3
    • PetsNo

    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)

    7 nights from £365

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    Characterful end-terraced stone cottage in pretty Ampleforth village. Beams, woodburning stove, conservatory. Cosy, well-equipped accommodation. Excellent pubs 3 mins walk. Helmsley 5 miles. (Ref. 12537)

    • 10% off - Fri 23rd Feb to 23rd Mar 2018

    7 nights from £316

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Charming stone cottage in Lastingham. Open fire, roll-top bath, countryside views. Quality accommodation. Excellent walking and touring base. Kirkbymoorside 7 miles. (Ref. 18645)

    Last booked within the last 2 days

    7 nights from £372

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    A delightful semi-detached cosy cottage, full of character, stone-flagged floor, wooden beams, woodburner, enclosed patio. Ideal for touring North York Moors National Park. Helmsley 3 miles. (Ref. 954791)

    7 nights from £293

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    • Sleeps5
    • Bedrooms2
    • PetsYes

    This lovely semi-detached cottage is on a working farm and is situated at the foot of Sutton Bank and close to Thirsk. Woodburner. Pet-friendly. Enclosed garden. (Ref. 957396)

    7 nights from £305

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    • Sleeps5
    • Bedrooms2
    • PetsYes

    A cosy semi-detached cottage situated in the village of Kirkbymoorside in Yorkshire. Pet friendly. Enclosed courtyard. Woodburner. Cosy layout. Pickering 6 miles; Helmsley 5 miles. (Ref. 963136)

    7 nights from £298

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    One of our Grade II Yorkshire cottages, a charming cottage with second floor lounge on edge of pretty Kirkbymoorside. Pickering 6 miles. (Ref. 3588)

    7 nights from £264

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    • Sleeps8
    • Bedrooms4
    • PetsNo

    Superb, detached house in village of Husthwaite, near Easingwold. Lovely accommodation, with a beautiful garden. A great base for touring the North York Moors, the Dales and east coast resorts. York 17 miles. (Ref. 941132)

    7 nights from £531

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    • Sleeps9
    • Bedrooms5
    • PetsNo

    Fabulous characterful property in Rosedale Abbey village. In heart of North York Moors. Beautiful conversion of the old post office. Spacious sitting room, modern kitchen. Excellent walking, cycling from doorstep. Pickering 10 miles. (Ref. 937421)

    7 nights from £580

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    • Sleeps5
    • Bedrooms3
    • PetsYes

    Charming, stone, period cottage in pretty village of Hutton-le-Hole. Open fire, cosy, comfortable accommodation. Private rear garden, lovely views over village green. Walkers' delight. Kirkbymoorside 3.5 miles. (Ref. 22745)

    Last booked yesterday

    7 nights from £376

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    • Sleeps3
    • Bedrooms2
    • PetsNo

    Delightful 18 century cottage offering cosy accommodation for families. First floor sitting room with woodburner and views of the castle. Off street parking for 1 car. Short stroll to all facilities. Kirbymoorside 6 miles. (Ref. 913657)

    7 nights from £285

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Pretty terraced cottage in sleepy hamlet on edge of Rosedale Abbey. Cosy, characterful accommodation with open fire and wonderful views over countryside. Superb walks from the door. Kirkbymoorside 7 miles. (Ref. 27834)

    7 nights from £281

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    • Sleeps2
    • Bedrooms1
    • PetsYes

    Quaint wooden chalet in a delightful and peaceful woodland setting on a complex. Comfortable, open plan accommodation. Excellent location for walking, touring and exploring this scenic area. Helmsley 5 miles. (Ref. 903687)

    7 nights from £212

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    Country detached cottage located in the village of Lastingham. Woodburning stove and piano. Countryside views. Kirkbymoorside 5.3 miles. (Ref. 947541)

    Last booked yesterday

    7 nights from £380

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Super property sleeping six in the pretty village of Crayke. Real fire, off street parking and within walking distance of the best pub in Yorkshire. (Ref. 11499)

    • 5% off - Fri 12th Jan to 2nd Feb 2018

    7 nights from £374

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    • Sleeps3
    • Bedrooms1
    • PetsYes

    Detached stone barn conversion in courtyard setting on owners' farm, near Kirkbymoorside. Single-storey accommodation, with a comfortable open plan living area and pretty bedroom. Easy access to North York Moors National Park. Kirkbymoorside 4 miles. (Ref. 929845)

    7 nights from £242

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    Detached chapel conversion in small hamlet of Rudland. Cathedral ceiling, woodburner, stream in garden. WiFi. Local to walking, cycling, castles and more. Kirkbymoorside 4.5 miles. (Ref. 2363)

    Last booked yesterday

    7 nights from £357

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    • Sleeps10
    • Bedrooms4
    • PetsYes

    Delightful semi-detached barn conversion in Farndale, 2 miles from Low Mills. Fabulous farmhouse kitchen with open fire. Excellent walking and cycling nearby. Kirkbymoorside 10 miles. (Ref. 1392)

    7 nights from £463

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    • Sleeps3
    • Bedrooms1
    • PetsNo

    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)

    7 nights from £238

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Delightful, stone-built, end-terraced cottage in pretty Wrelton. Spacious kitchen, four poster bed, patio. Perfect base for walking and exploring. Pickering 3 miles. (Ref. 4109)

    7 nights from £271

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Just show me Helmsley Cottages

Please find below a selection of self catering holiday cottages to rent in Helmsley, Yorkshire.

On the borders of the North York Moors National Park, this lovely little market town is a haven for walkers as it's the starting point of the Ebor Way, a long distance trail that connects the Cleveland Way and Dales Way.

Of course, the National Park is a playground for all kinds of other outdoor activities too like cycling, horse riding, fishing and golf. Plus it's only a short distance from our Helmsley cottages to the coast if you fancy a day on the beach.

Fresh air and exercise create healthy appetites and Helmsley's pubs, tearooms and restaurants are extremely inviting - worth a mention is the Black Swan for fine food amid swish surroundings. There are also stylish shops selling everything from gifts and crafts to country wear, along with a weekly street market.

Attractions include the beautiful Parish Church, a thriving Arts Centre and Helmsley Castle, a magnificent ruined Norman keep overlooking the town, with displays of archaeological treasures and a fascinating interactive exhibition. In the shadow of the castle, just a short distance from the town centre, lies the estate of Duncombe Park and its National Nature Reserve. Spend a day here admiring ancient trees and colourful birdlife and look out for the five-acre Helmsley Walled Garden, a working kitchen garden brimming with special collections of Yorkshire apple trees, Victorian vines and numerous varieties of clematis.

And don't miss a trip to Rievaulx Abbey, an amazing Gothic ruin just a couple of miles away; or Nunnington Hall, a stunning 17th Century manor house.

Sounds appealing? Then book a Helmsley cottage.