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Find cottages in Helmsley

The charming market town of Helmsley is situated on the edge of the North York Moors National Park and is the perfect place for a cottage break.

The focal point of the town is its square and ancient cross, which is surrounded on all sides by cosy pubs, boutique and speciality shops and restaurants. Every Friday there is a market that sells local produce.

Helmsley has a fascinating history, with many of its building''s dating back to the 17th Century. The town''s dramatic castle sits on a grassy knoll overlooking the town and tells a fascinating story through its medieval, Tudor and Victorian remains, and 100 foot-high tower. The Helmsley Walled Garden lies just below the castle which has been lovingly restored back to its original Victorian beauty.

Access to some of the most beautiful landscapes in Britain is straight from the cottage door; with mile after mile of rolling heather moors and pretty villages that make up the North York Moors National Park; nearby is the expanse of Duncombe Park, one of Yorkshire''s foremost historic houses. Also close by are the impressive Byland Abbey ruins, once one of the greatest monasteries in England and equally as inspiring is Rievaulx Abbey where 12th Century monks once lived and worshipped.

On a warm day why not take a dip in the town''s open air swimming pool or enjoy lunch in one of the local pubs, all former coaching inns, which sit around the square.

To enjoy the area see our selection of Helmsley holiday cottages.

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  • Highfield Barn

    Scackleton, nr. Hovingham

    Grade
    2
    1
    2
    1
    Ref: 24873

    This stone built former granary, attached to the owners’ home, has been sympathetically converted to offer first floor holiday accommodation of a very good standard, within the stunning countryside of the Howardian Hills. A designated AONB, between the North York Moors National Park, The Yorkshire Wolds and the Vale of York, with an abundance of walks, scenic villages and country houses. Coastal resorts and the Yorkshire Dales are within easy reach. Castle Howard, the picturesque village of Hovingham and the traditional market town of Helmsley are all close by. The vibrant city of York is just 18 miles away. Shop and pub 3 miles.

    Steps to entrance. All on first floor: Living room with double sofa bed (for alternative sleeping)/dining room/kitchen. 1 double (6ft zip and link) bedroom. Shower room. Separate toilet.

    Oil central heating, electricity, bed linen and towels included. Freeview TV. DVD. CD. Electric cooker. Microwave. Access to washing machine. Fridge/freezer. Wi-fi. Shared garden. Sitting-out area and furniture. Parking (2 cars). Free range eggs provided from owners hens. No smoking.

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  • Gardener’s Cottage

    Oulston, nr. Easingwold

    Grade
    2
    1
    3
    1
    Ref: IAH

    This idyllic and cosy hideaway for two, in the centre of the peaceful village of Oulston, offers spacious and comfortable holiday accommodation. Built in the 1820s, it is Grade II listed and has its own large secluded garden. The nearby Howardian Hills are an Area of Outstanding Natural Beauty, with excellent walking, and there is plenty to see and do within easy driving distance. Easingwold 4 miles. York 16 miles. Thirsk 12 miles. Rievaulx Abbey, Helmsley Castle and Duncombe Park, all within
    15 miles. Coxwold (2 miles) is a very attractive stone-built village. Shop 2 miles, good village pub at Crayke, 2 miles.

    Entrance lobby. Attractive, spacious, beamed sitting room with open fire and dining area. Small well-fitted kitchen. Rear hall with door to garden. Bathroom with over-bath shower and toilet. First floor: Large landing. Pretty, beamed double bedroom with original pine floor and cast-iron fireplace.

    • Open fire – fuel included
    • Electricity, full NSH, convector heaters, bed linen and towels included
    • Flatscreen TV
    • DVD
    • Microwave
    • Washing machine
    • Tumble dryer (in outhouse)
    • Large garden with furniture
    • Parking

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  • Highfield Barn

    Helmsley

    Grade
    2
    1
    0
    1
    Ref: DC4694
    Along a quiet lane with lovely views, this superb barn conversion is situated on the edge of the North York Moors National Park, a haven for walkers and outdoor enthusiasts. The village inn is a short stroll and there is an excellent farmshop and tearoom less than a mile away, whilst the picturesque market towns of Helmsley and Kirkbymoorside are just three miles. There are numerous attractions in the area including the Steam Preservation Railway at Pickering, Dalby Forest and Castle Howard. Coastal resorts of Whitby, Scarborough and Filey are within easy driving distance.

    Ground Floor: With electric panel heating and comprising:
    Sitting/dining room: with log burning stove, TV and radio/CD player.
    Kitchen/diner: with oven, hob, microwave, fridge, washer and iron.
    Spiral solid beech wood staircase leading to...

    First Floor: Bedroom 1: with double bed and exposed beams.
    Shower room: with shower, WC, basin and heated towel rail.

    Bed linen and towels provided. Patio with table, chairs and BBQ. Private parking for two cars.

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  • Low Crossett Cottage

    Chop Gate, nr. Helmsley

    Grade
    2
    1
    0
    1
    Ref: UKC197

    The valley of Bilsdale within the spectacular North York Moors National Park is the setting for Low Crossett Cottage and is the ideal location for guests wanting to enjoy a romantic break. This detached 200 year old barn conversion, located on a small working farm in this unspoilt area, has been tastefully converted throughout and still retains many original features, yet offers all the home comforts. Vaulted beam ceilings, wooden floors and the woodburner add to the charm of this warm and welcoming cottage. Perfect for walkers and cyclists, or if you don’t want to venture out, Low Crossett Cottage provides all the facilities you would require for a relaxing break. The south-facing garden is the perfect spot to sit, relax and enjoy the stunning views across the valley.

    Perfect for exploring the North York Moors National Park, guests will find many walks suitable for all ages and abilities. Although rural in location, there are many local attractions and places to explore in the surrounding area. For guests who enjoy history, a visit the abbey ruins at Rievaulx, Rosedale and Byland is a must, and also Castle Howard, renowned as Yorkshire’s finest historic house and estate. Enjoy breathtaking views from the castle across the magnificent Howardian Hills before exploring the beautiful landscaped gardens, garden centre, coffee shop and farm shop. Nearby Duncombe Park also has beautiful landscaped gardens and the International Bird of Prey Centre.

    Yorkshire’s heritage coastline has lovely sandy beaches and picturesque towns and villages. Why not visit the historic town of Whitby with its narrow cobbled streets and abbey, or the coastal hamlet of Staithes. For train enthusiasts, this is the perfect opportunity to enjoy a trip on the steam train from Pickering to Whitby. A little further afield but still within easy driving distance, take a trip to the historic city of York with its famous minster, Roman walls, cobbled streets and ever popular tea rooms and quaint cafes.

    All on one level and very well presented throughout, Low Crossett Cottage offers a warm welcome at any time of the year. The open plan living room, dining room and kitchen is filled with character and charm. There is a dining table and chairs, large sofa and armchair, flatscreen Freeview TV, DVD player, digital radio and Bluetooth speaker, and wi-fi is provided free of charge. The well-equipped kitchen has an electric cooker, fridge/freezer, microwave and washing machine. There is a large and spacious double bedroom with a kingsize bed and super views across the surrounding countryside. The en-suite shower room offers a large shower cubicle with multi-head shower and there is also a separate toilet. Shop 8½ miles, pub and restaurant 3½ miles.

    All on ground floor: Step to living/dining room/kitchen with beams and wooden floor. Step to 1 kingsize bedroom with en-suite shower room and toilet. Separate toilet.

    Woodburner in living room (initial fuel included). Oil central heating, electricity, bed linen and towels included. 28" Freeview TV. DVD. DAB radio. Electric cooker. Microwave. Washing machine. Fridge/freezer. Wi-Fi. Small lawned garden with sitting-out area and furniture. Parking (1 car). Natural water supply from spring. Welcome pack. No smoking. NB: Some internal steps.

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  • Laskill Grange - Bridge Cottage

    Bilsdale, nr. Helmsley

    Grade
    2
    1
    1
    1
    Ref: W43184

    Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well-equipped holiday cottages (refs W43183, W43184 and W43185) stand in a landscaped courtyard, close to the owner’s farmhouse. Enjoy farmhouse breakfasts at Laskill Grange, or across the drive at Laskill Country House, the owners’ daughter offers home cooked evening meals or ready prepared frozen meals. There are 70 acres of beautifully tended grounds and a shared terrace garden with its small lake and river frontage. The surrounding countryside views are superb, and there is excellent walking from the doorstep. Long distance footpaths along this area’s Heritage coastline, and the Cleveland Way, offer perfect terrain for walkers and cyclists. Visit Ryedale Folk Museum and Rosedale Abbey, or for a day out, try the North York Moors Railway. Whitby has miles of sandy beaches and an ancient abbey overlooking its harbour. Scarborough, Staithes, Runswick Bay and Sandsend are within 20 miles. Horse racing at Thirsk, Wetherby and York, 25 miles. Helmsley has Duncombe Park and a castle. Shop, pub and restaurant 2 miles.

    All on ground floor: Living/dining room/kitchen. 1 double bedroom. Bathroom with shower over bath and toilet.

    Electricity and oil central heating included (£25per week, £15 per short break October-April). Microwave. Washing machine. Parking for 1 car.

    All properties: Electric woodburner in living room included. Bed linen and towels included. Cot and high chair on request. DVD. CD. Electric cooker. Dishwasher. Shared freezer. Wi-fi. Sitting-out area and furniture. Shared terrace garden. Shared 70-acre grounds. Shared conservatory with communal wi-fi access. Shared hot tub. Natural water supply from spring. No smoking. NB: There is a small lake and river frontage within the garden.

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  • Laskill Grange - Foxglove Cottage

    Bilsdale, nr. Helmsley

    Grade
    2
    1
    1
    1
    Ref: W43183

    Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well-equipped holiday cottages (refs W43183, W43184 and W43185) stand in a landscaped courtyard, close to the owner’s farmhouse. Enjoy farmhouse breakfasts at Laskill Grange, or across the drive at Laskill Country House, the owners’ daughter offers home cooked evening meals or ready prepared frozen meals. There are 70 acres of beautifully tended grounds and a shared terrace garden with its small lake and river frontage. The surrounding countryside views are superb, and there is excellent walking from the doorstep. Long distance footpaths along this area’s Heritage coastline, and the Cleveland Way, offer perfect terrain for walkers and cyclists. Visit Ryedale Folk Museum and Rosedale Abbey, or for a day out, try the North York Moors Railway. Whitby has miles of sandy beaches and an ancient abbey overlooking its harbour. Scarborough, Staithes, Runswick Bay and Sandsend are within 20 miles. Horse racing at Thirsk, Wetherby and York, 25 miles. Helmsley has Duncombe Park and a castle. Shop, pub and restaurant 2 miles.

    All on ground floor: Living/dining room/kitchen. 1 double (5ft) bedroom with en-suite bathroom with shower over bath and toilet.

    Electricity and electric heaters included (£25per week, £15 per short break October-April). Microwave. Laundry service at cost. Parking for 1 car.

    All properties: Electric woodburner in living room included. Bed linen and towels included. Cot and high chair on request. DVD. CD. Electric cooker. Dishwasher. Shared freezer. Wi-fi. Sitting-out area and furniture. Shared terrace garden. Shared 70-acre grounds. Shared conservatory with communal wi-fi access. Shared hot tub. Natural water supply from spring. No smoking. NB: There is a small lake and river frontage within the garden.

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  • Laskill Grange - Rievaulx Cottage

    Bilsdale, nr. Helmsley

    Grade
    2
    1
    1
    1
    Ref: W43185

    Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well-equipped holiday cottages (refs W43183, W43184 and W43185) stand in a landscaped courtyard, close to the owner’s farmhouse. Enjoy farmhouse breakfasts at Laskill Grange, or across the drive at Laskill Country House, the owners’ daughter offers home cooked evening meals or ready prepared frozen meals. There are 70 acres of beautifully tended grounds and a shared terrace garden with its small lake and river frontage. The surrounding countryside views are superb, and there is excellent walking from the doorstep. Long distance footpaths along this area’s Heritage coastline, and the Cleveland Way, offer perfect terrain for walkers and cyclists. Visit Ryedale Folk Museum and Rosedale Abbey, or for a day out, try the North York Moors Railway. Whitby has miles of sandy beaches and an ancient abbey overlooking its harbour. Scarborough, Staithes, Runswick Bay and Sandsend are within 20 miles. Horse racing at Thirsk, Wetherby and York, 25 miles. Helmsley has Duncombe Park and a castle. Shop, pub and restaurant 2 miles.

    All on ground floor: Living/dining room/kitchen. 1 double bedroom (6ft zip and link) with en-suite bathroom with shower over bath and toilet.

    Electricity and electric heaters included. Electricity included (£25per week, £15 per short break October-April). Laundry service at cost. Parking (2 cars).

    All properties: Electric woodburner in living room included. Bed linen and towels included. Cot and high chair on request. DVD. CD. Electric cooker. Dishwasher. Shared freezer. Wi-fi. Sitting-out area and furniture. Shared terrace garden. Shared 70-acre grounds. Shared conservatory with communal wi-fi access. Shared hot tub. Natural water supply from spring. No smoking. NB: There is a small lake and river frontage within the garden.

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  • Garden Cottage

    Nawton near Helmsley

    Grade
    2
    1
    2
    1
    Ref: CC233040
    Situated just 3 miles from the pretty market town of Helmsley is this lovely, spacious bungalow nestled in the owners beautiful gardens. It has been furnished and decorated to a high standard and offers excellent accommodation for couples looking to explore this stunning area.

    Ground Floor: The property is heated by gas central heating and comprises:

    Lounge/Kitchen/Diner: With TV/Freeview, DVD, radio/CD player, electric fire, electric oven and hob, fridge/freezer, microwave and washing machine. 

    Bedroom: With Zip ‘n’ link beds for either super King-size or twin beds(please request on booking)
     
    Bathroom 1: With bath and shower cubicle, WC, basin and shaver point.

    All power, heating, bed linen and towels included. Enclosed garden with furniture. Parking for 2 cars. Two dogs welcome, to be kept on a lead at all times (livestock).

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  • Clematis Cottage

    Helmsley

    Grade
    3
    2
    0
    1
    Ref: CC233018
    Clematis Cottage is situated in a quiet area in the lovely market town of Helmsley. It is an ideal base to enjoy and discover all North Yorkshire has to offer. You will find pretty villages, exhilarating coastline and spectacular scenery all close by, only 40 minutes from the beautiful city of York with the stunning York Minster and quaint cobble streets. This lovely well equipped modern house has been decorated to a high standard and is ideal for mature couples, families and people with limited mobility who want to get away and enjoy these tranquil surroundings. The spacious garden at the rear of the property is ideal for children or just to relax on a summers evening.The secure garage is ideal for keen cyclists and there are plenty of cycle trails in the area.
    Helmsley is where the famous 110 mile Cleveland Way begins so there is excellent walking right on your doorstep. It boasts excellent shops and restaurants and the impressive castle with its 12th century ruins towers over the town and can be seen from the kitchen window of the property. There is and open air swimming pool open from June until September for the kids to enjoy.Flamingo Land Park and Zoo is only 20 miles away, which is a fun packed day for all the family and the North Yorkshire Moors Steam Train which will take you from Pickering to Whitby and back is well worth a trip. Whatever you enjoy doing on holiday this property is ideally situated to enable you to explore everything this area has to offer.

    Ground Floor: Property has gas fired central heating and comprises:
    Lounge/Diner: With TV, DVD player, radio and CD player
    Kitchen: With electric oven and hob, microwave, washing machine, fridge with ice box and dishwasher.
    Bedroom 1: With double bed
    Bedroom 2: With single bed and with patio door leading to the rear garden area.
    Bathroom: With bath and shower over, WC, wash basin, heated towel rail and shaver point.
    Cloakroom: With storage for boots and coats.

    All fuel, power, bed linen and towels included.Pretty enclosed  garden with pond (small children beware!), patio and garden furniture. Access to garage with tumble dryer, freezer and storage for bicycles or motorbikes. Parking for 1 car.

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  • Honeysuckle Cottage

    Oswaldkirk, nr. Helmsley

    Grade
    3
    2
    1
    1
    Ref: 17199

    With outstanding views over the Howardian Hills, in an AONB, this holiday cottage offers very comfortable accommodation at any time of the year. Situated on the edge of the Yorkshire Moors National Park, there is excellent walking right from the doorstep. The market town of Helmsley with picturesque square, quality shops and variety of restaurants, 4 miles. Places of interest locally include Duncombe Park, Nunnington Hall, Castle Howard and Rievaulx Abbey. Hang gliding from Sutton Bank, 6 miles. York, 20 miles. Whitby, 30 miles. Shops 2 miles, inn/restaurant 500 yards.

    Ground floor: Living/dining room with sofa bed (for alternative sleeping) and beams. Dining area. Kitchen. Utility room. First floor: 2 bedrooms: 1 double, 1 double (4ft 3in). Shower room with toilet. Maximum occupancy 3 guests.

    Open fire in living room included. Solid fuel heaters, electricity, bed linen and towels included. DVD. Electric cooker. Microwave. Washer/dryer. Dishwasher. Fridge/freezer. Wi-fi. Sitting out area and furniture. Parking (1 car). NB: Drop from patio to road.

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  • Manor Farm Cottage

    Scawton, near Helmsley

    Grade
    3
    2
    1
    1
    Ref: UK2058
    Standing within the North York Moors National Park this cosy detached barn conversion enjoys stunning countryside views. Sheep graze on the owner’s farmland adjacent to the delightful cottage garden and visitors are assured of a relaxing holiday in this tranquil location. There are numerous walking and cycling trails from the doorstep and you can store your bikes in one of the outbuildings or hire cycles from the local hire company where there are a great selection of bikes to suit all abilities. The extensive ruins of Rievaulx Abbey, an English Heritage site, are just a 5-minute drive away, where there is an informative museum and lovely tearoom. Explore the market town of Helmsley, 4 miles, with its arts centre, walled garden, castle ruins and Centre for Birds of Prey. Enjoy the award-winning eateries and the town’s very own brewery, alongside the interesting and unique stores, galleries and boutiques. Thirsk, 10 miles, is set in the Vale of Mowbray and James Herriot, local vet and author, was born here and his house and surgery have been converted into an award-winning museum where visitors can learn of the life he wrote about in ‘All Creatures Great and Small’. The seaside resorts of Scarborough, Whitby and Filey and the ancient city of York are all within an hour’s drive. Shop 4 miles, pub and restaurant 1½ miles.

    Ground Floor: All on the ground floor.
    Living/dining room:
    With Freeview TV, DVD player and beam.
    Kitchen: With breakfast area, electric cooker, microwave, fridge/freezer and washing machine.
    Bedroom 1: With double bed.
    Bedroom 2: With ¾ double bed.
    Bathroom: With shower over bath, and toilet.

    Oil central heating, electricity, bed linen and towels included. Highchair. Lawned garden with sitting-out area and garden furniture. Bike store. Private parking for 2 cars. No smoking.

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  • Crossbill Cottage

    Chopgate near Stokesley

    Grade
    3
    2
    0
    1
    Ref: CC233062
    Crossbill Cottage is a beautiful barn conversion, formerly a Cow Byre that has been completed in 2011 into a delightful, modern cottage. It is situated in a secluded, tranquil location at the end of a farm track in a rural position on the edge of the North Yorkshire Moors. The original beams, high ceilings and open plan living area give the property a light, spacious feel to it. The decor and furnishings have been tastefully done and finished off to a very high standard making this cottage an excellent base for couples and families looking to explore this lovely, scenic area. Crossbill Cottage gets its name from the exceptionally rare two barred crossbill which was famously sighted here and has brought many bird watchers from around the globe. The bird life is exceptional in this area making a stay here an ideal location for keen bird watchers.

    Ground Floor: Property is heated by electric heaters and under floor heating and comprises:
    Lounge/Kitchen/Diner: With electric stove, Freeview TV, blue ray/DVD/CD player, digital radio, Bose docking station, electric oven and hob, microwave, fridge/freezer and washing machine
    Bedroom 1: With king size bed and en suite double shower cubicle, WC and wash basin (under floor heating)
    Cloakroom: With WC and wash basin

    First Floor: Bedroom 2: With single bed

    All power, heating, bed linen and towels included. Cot and high chair provided by request. Wi-fi available.Enclosed garden with furniture, barbecue and children’s play house. Parking for 2 cars. Large unfenced pond/children must be supervised.Visit Britain Gold awarded property.

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