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Helmsley Vacation Rentals

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    Travelers to Helmsley are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 29 Rentals in Helmsley
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    Self Catering 3 Bedroom1 / 10
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    High Farm, Beadlam Rigg1 / 10
    (15)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    The Stables1 / 21
    (6)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    PEG'S COTTAGE, detached, ground floor, WiFi, gas fire, garden with furniture, ne1 / 9
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 15, 2017
    We have just returned from a week's break at Pegs Cottage in Pockley, close to Helmsley. It was a perfect break for us and our two dogs who were secure in the grounds of the...
    Reviewed September 9, 2017
    Good location only a few minutes away from Helmsley with its quaint shops and vibrant Friday markets and from the abbey ruins at Rievaulx and Castle Howard with its extensive...
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    About this property
    This charming, detached stone cottage, set in a hamlet close to the North Yorkshire market town of Helmsley, can sleep two people in one double bedroom.Peg's Cottage, a delightful, detached, stone cottage, is set solely over the ground floor in a little hamlet just two miles from the market town of...
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    Helmsley, North Yorkshire YO62 7TE
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Low Crossett Cottage in North York Moors.  Short Breaks & WiFi.1 / 18
    (6)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Private Yard
    • Outdoor Dining Area
    • Central Heating
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 30, 2018
    Well-equipped and comfortable cottage for two people with superior views. Excellent location for visiting sites throughout north Yorkshire.
    Reviewed April 24, 2018
    A lovely cottage in a stunning location secluded with terrific views couldn't have asked for more. The cottage was well equipped with a good size fridge/freezer, very...
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    About this property
    One bedroom barn conversion set within the North York Moors National Park in the valley of Bilsdale. This south facing 200 year old character property has been tastefully converted and retains many original features whilst introducing the 21st century. Large open plan living space with vaulted beam...
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    Helmsley, North Yorkshire TS9 7LH
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This ground floor barn conversion is located in the hamlet of Chop Gate between Helmsley and Stokesley in North Yorkshire and can sleep four people in two bedrooms. Witches Cottage is a terraced barn conversion cottage on a working farm in the tiny hamlet of Chop Gates, ten miles north of Helmesley...
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    Hawnby, Helmsley TS9 7LA
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Housekeeping Included
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, dog friendly, idyllic rural setting close to tourist attractions Sproxton Hall Cottages are situated off a quiet road in the hamlet of Sproxton. Sproxton is less than 2 miles from the picturesque market town of Helmsley. Close by are Sutton Bank, Rievaulx Abbey, and Duncombe Park....
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    Helmsley, North Yorkshire YO62 5EQ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Farmhouse With Large Sunny Garden, Log Burning Stoves & Plenty Of Space To Relax1 / 16
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2017
    We booked this property after looking at several in the area but couldn’t find anything else that came close to the quality we saw in this one. When contacting the owner she...
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    About this property
    The house is fully furnished with TV, Wi-Fi, BT Vision, DVD player, CD player: comprising three reception rooms, two double bedrooms and a twin bedroom. Overall it can easily accommodate 6 people. The master bedroom has oak furniture and a wood burning stove. All linen bedding and towels are...
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    Helmsley, North Yorkshire YO62 5DD
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, character cottage is in the town of Helmsley in Yorkshire and can sleep eight people in four bedrooms. Osbourne Cottage is a charming, character cottage is in the town of Helmsley in Yorkshire. The cottage sleeps eight people in four bedrooms which are made up of two doubles with...
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    Helmsley, North Yorkshire YO62 5AB
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    LITTLE MANOR FARM COTTAGE, romantic, WiFi, character holiday cottage in Nawton,1 / 8
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming property has one double bedroom with en suite and is an ideal romantic retreat at any time of the year.Situated just outside the pretty village of Nawton and a mere four miles from Kirkbymoorside and Helmsley is this delightful cottage - a cosy stone-built detached property. This...
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    Nawton, Helmsley YO62 7TU
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Safari Tent1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Yard
    • Parking
    • Grill
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 1, 2016
    Booked for 2 nights to go to a wedding nearby, met by friendly staff, safari tent was clean, and had just about everything we needed to cook breakfast, and was cosy with the log...
    Reviewed July 24, 2016
    Just got home after an amazing stay here we were made so welcome nothing was a problem for jenny and all the staff beautiful tents amazing food stunning location will definatly...
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    About this property
    Canadian Fields is located within the North York Moors National Park, just off the A170 which runs between Helmsley and Scarborough, 3 miles from Helmsley & 3 miles from Kirkbymoorside. We are a family friendly site, ideally located for exploring the nearby market towns of Thirsk, Helmsley,...
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    Nawton, Helmsley YO62 7SD
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ORCHARD COTTAGE, character, woodburning stove, in Helmsley, Ref 9136571 / 11
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 23, 2018
    It was our first time staying in Orchard Cottage in Helmsley and we were not disappointed.The cottage is in a central location and despite it being near the castle and the main...
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    About this property
    A delightful character cottage in the town of Helmsley in Yorkshire which can sleep four people in two bedrooms. Orchard Cottage is a delightful character cottage in the town of Helmsley in Yorkshire. The cottage can sleep four people in two ground floor bedrooms which are made up of a double and...
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    Helmsley, North Yorkshire YO62 5AB
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    CORONATION COTTAGE, woodburner, wet room, all ground floor, fantastic location,1 / 11
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 22, 2018
    June 2018 was our fourth visit to Coronation Cottage. It has everything we need as we get a bit older... walk in wet room, everything on the ground floor and level access to the...
    Reviewed March 22, 2018
    Stayed for 3 nights in the beautiful market town of Helmsley. Cottage has everything you need and is very comfortable. Will be back!
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    About this property
    This charming cottage sits in the market town of Helmsley in North Yorkshire, sleeping four people in two bedrooms.Coronation Cottage is a stone-built cottage tucked away in a central position in the market town of Helmsley, North Yorkshire. With two bedrooms, including one king-size double and one...
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    Helmsley, North Yorkshire YO62 5DX
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This barn conversion is in the hamlet of Chop Gate, ten miles from Helmsley and sleeps four people in two bedrooms.Clack Cat Cottage is a Grade II listed barn conversion, one of three, in the hamlet of Chop Gate, ten miles from Helmsley which sleeps four people in two bedrooms. The cottage has a...
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    Hawnby, Helmsley TS9 7LA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Central Heating
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In a magnificent position on the edge of the North Yorkshire Moors National Park and within the Howardian Hills Area of Outstanding Natural Beauty, Ryedale Cottage offers far reaching views of countryside and is an ideal base for coast & York. The cottage is a converted 18th century stone farm...
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    Helmsley, North Yorkshire YO62 5EQ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    OWL COTTAGE all ground floor, on working farm in Helmsley Ref 9311571 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 17, 2018
    So glad I found this cottage - absolutely perfect and exactly as described. Incredibly peaceful and beautiful location, lovely owners and everything was spotless in this very...
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    About this property
    This ground floor barn conversion is located in the hamlet of Chop Gate between Helmsley and Stokesley in North Yorkshire and can sleep two people in one bedroom. Owl Cottage is a terraced barn conversion cottage on a working farm in the tiny hamlet of Chop Gates, ten miles north of Helmsley in the...
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    Hawnby, Helmsley TS9 7LA
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This mid-terrace cottage is in the market town of Helmsley near to Kirkbymoorside and can sleep four people in two bedrooms. 8 Pottergate Mews is a lovely mid-terrace cottage situated in the market town of Helmsley just six miles from Kirkbymoorside, North Yorkshire. The cottage can sleep four...
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    Helmsley, North Yorkshire YO62 5DJ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This end-terrace cottage is located in Helmsley and can sleep five people in three bedrooms.Ivy Cottage is a delightful end-terrace cottage overlooking a village green close to the centre of Helmsley in the North York Moors National Park. The cottage sleeps five people and has a double bedroom, a...
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    Helmsley, North Yorkshire YO62 5AW
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    ARCHWAY HOUSE, pet-friendly, peaceful location, four poster bed, two bathrooms,1 / 13
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2017
    The cottage is in a perfect location for families looking to visit the many English Heritage/National Trust locations around the area. We are a family of four and we chose the...
    Reviewed December 14, 2016
    This is by far one of the best holiday cottages I have stayed in. Clean cosy comfortable, lovely to return to after a day out. Facilities are second to none, top quality and...
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    About this property
    This super, end-terrace cottage in Nawton, North Yorkshire, sleeps five people in three bedrooms.Archway House is a charming, end-terrace cottage next to the owner's other holiday home, in the North Yorkshire village of Nawton. With three bedrooms including a fantastic four poster king-size double,...
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    Nawton, Helmsley YO62
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Central Heating
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Riccaldale Cottage is in a magnificent position on the edge of the North Yorkshire Moors National Park, offering far reaching views of the Howardian Hills (Area of Outstanding Natural Beauty). The cottage is an ideal base for moors, coast & York. Riccaldale is a cosy, non-smoking cottage, which is...
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    Helmsley, North Yorkshire YO62 5EQ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Housekeeping Included
    • Central Heating
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    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In a magnificent position on the edge of the North Yorkshire Moors National Park, and located within the Howardian Hills Area of Outstanding Natural Beauty, the cottage and grounds offer far reaching views of the wooded valleys and countryside. Kirkdale Cottage is a converted farm building, which...
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    Helmsley, North Yorkshire YO62 5EQ
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    44 ELMSLAC ROAD, pet-friendly, spacious interior, conservatory, Ref 9712511 / 20
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2018
    Family run house for families! We ate strawberries from the garden and sat in the sunny garden. Plenty of kitchen ware, it really didn't matter if it didn't all match! The...
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    About this property
    This cottage is located in the village of Helmsley near Kirkbymoorside and can sleep eight people in four bedrooms.44 Elmslac Road is a wonderful cottage situated in the village of Helmsley in North Yorkshire. Hosting four bedrooms; 2 doubles, 1 twin and adult bunks a bathroom, and a...
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    Helmsley, North Yorkshire YO62 5AW
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    OAKLEIGH HOUSE, attractive cottage, near walks, attractions and amenities, two b1 / 11
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    Reviewed June 15, 2017
    The cottage overall was very good and we would recommend the cottage to anyone who wants a quality accommodation. We had a problem with a leak from the upstairs bathroom that...
    Reviewed September 5, 2015
    Located in a quiet little village. Well decorated and fully furnished, spacious and homely. Not far from the charming little town of Helmsley where you can get your grocery from...
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    About this property
    This pretty, mid-terraced cottage in Nawton, North Yorkshire, sleeps four people in two bedrooms.Oakleigh House is a delightful, terraced cottage set in the village of Nawton, adjoining the owner's second holiday home. With one double and one twin bedroom, the property can sleep four people....
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    Nawton, Helmsley YO62
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    This shpeherd's hut is located near the village of Helmsley close to Kirkbymoorside, and can sleep two people in one bedroom.Shepherd's Hut is a characterful shepherd's hut situated near the village of Helmsley, North Yorkshire. Hosting one double bed, and a shower room, this property can sleep up...
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    Hawnby, Helmsley YO62 5NE
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    CASTLE VIEW, pet friendly, character holiday cottage, with a garden in Helmsley,1 / 22
    (26)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Reviewed May 11, 2018
    Beautiful house.Lovely gardenIdeal location So warm and cosySuper memories of a fabulous weekOne word says it all!
    Reviewed April 30, 2018
    Firstly, reviews can be subjective. If you spent £650 for a week here your view would be different from someone spending over £2000. This view is based on us spending around...
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    About this property
    With four spacious, sunny bedrooms – able to sleep a total of eleven people – this property is best suited to larger groups and families.Just a few minutes walk from the centre of the pretty market town of Helmsley is this charming property - a superb, semi-detached house in a quiet position. This...
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    Helmsley, North Yorkshire YO62 5AL
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This stone-built mews cottage is situated in a quiet part of Helmsley in the North York Moors National Park and can sleep four people in two bedrooms.Mews Cottage is a stone-built mews cottage situated within Helmsley in the North York Moors National Park. It offers two bedrooms, one double and one...
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    Helmsley, North Yorkshire YO62 5DJ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful detached period property in the village of Beadlam near Helmsley and can sleep 8 people in four bedrooms.Auburn House is a beautiful detached period property in the village of Beadlam near Helmsley. The cottage can sleep eight people in four bedrooms which are made up of three doubles...
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    Helmsley, North Yorkshire YO62 7SY
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    WETHERCOTE COTTAGE, family friendly, character holiday cottage, with a garden in1 / 12
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed March 19, 2017
    Just back from Wethercote, had a great time. Cottage is lovely, very clean and sooo warm, I even had to put the heating off and has everything you could need. Family are lovely...
    Reviewed June 1, 2016
    Cottage overall was fine, although double mattress needs replaced and some small glasses needed as pint ones are too big. There is no freezer although owners let us share theirs...
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    About this property
    This two bedroom house is able to sleep up to four people and is located close to the village of Helmsley.This traditional, stone-built, cottage is a semi-detached property that adjoins the owner's house on a working livestock farm near Old Byland. Just seven miles from the market town of Helmsley,...
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    Helmsley, North Yorkshire YO7 2HW
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Helmsley 21 km from Rosedale Abbey: Comfortable house 'Carlton', detached. In the centre of Helmsley, in a sunny position. Private: garden with lawn, pond. Patio, garden furniture, parking space n 3. Shop, restaurant, bar 350 m, bus stop 'Carlton Road' 50 m. Golf course (18 hole) 10 km, walking...
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    Location Information
    Helmsley, North Yorkshire YO62 5HA
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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