Below is a list of holiday cottages in Upper Helmsley, the list includes Upper Helmsley self catering cottages, apartments, flats and rentals. The list also includes cottages within 30km of Upper Helmsley.
| Little Stonewold |
| York, Yorkshire and Cleveland |
| Sleeps: 3 Low Price: 200 High Price: 275. |
| This property is situated in York, it is located approximately 11.34 km from Upper Helmsley. Little Stonewold sleeps a maximum of 2 people and the low season price starts from 200. |
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| The Mill House |
| MALTON, Yorkshire and Cleveland |
| Sleeps: 2 Low Price: 220 High Price: 275. |
| This property is situated in MALTON, it is located approximately 13.59 km from Upper Helmsley. The Mill House sleeps a maximum of 3 people and the low season price starts from 220. |
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| Easthorpe Lodge |
| Malton, Yorkshire and Cleveland |
| Sleeps: 3 Low Price: 261 High Price: 575. |
| This property is situated in Malton, it is located approximately 15.69 km from Upper Helmsley. Easthorpe Lodge sleeps a maximum of 4 people and the low season price starts from 261. |
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| Dixieland Farmhouse |
| Slingsby, Yorkshire and Cleveland |
| Sleeps: 4 Low Price: 250 High Price: 700. |
| This property is situated in Slingsby, it is located approximately 18.19 km from Upper Helmsley. Dixieland Farmhouse sleeps a maximum of 12 people and the low season price starts from 250. |
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| Hawtree Cottage |
| York, Yorkshire and Cleveland |
| Sleeps: 12 Low Price: 395 High Price: 575. |
| This property is situated in York, it is located approximately 24.59 km from Upper Helmsley. Hawtree Cottage sleeps a maximum of 5 people and the low season price starts from 395. |
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| Old Cobbler's Cottage |
| North Dalton, Yorkshire and Cleveland |
| Sleeps: 5 Low Price: 220 High Price: 425. |
| This property is situated in North Dalton, it is located approximately 24.73 km from Upper Helmsley. Old Cobbler's Cottage sleeps a maximum of 4 people and the low season price starts from 220. |
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| Bruno's Lodge |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 4 Low Price: 155 High Price: 275. |
| This property is situated in Kirkbymoorside, it is located approximately 28.03 km from Upper Helmsley. Bruno's Lodge sleeps a maximum of 4 people and the low season price starts from 155. |
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| The Chalet |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 4 Low Price: 230 High Price: 475. |
| This property is situated in Kirkbymoorside, it is located approximately 28.03 km from Upper Helmsley. The Chalet sleeps a maximum of 6 people and the low season price starts from 230. |
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| Annie's Cottage |
| Kirkbyymoorside, Yorkshire and Cleveland |
| Sleeps: 6 Low Price: 240 High Price: 420. |
| This property is situated in Kirkbyymoorside, it is located approximately 28.03 km from Upper Helmsley. Annie's Cottage sleeps a maximum of 4 people and the low season price starts from 240. |
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| Greystones |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 4 Low Price: 230 High Price: 515. |
| This property is situated in Kirkbymoorside, it is located approximately 28.03 km from Upper Helmsley. Greystones sleeps a maximum of 6 people and the low season price starts from 230. |
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| Penny's Place |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 6 Low Price: 155 High Price: 275. |
| This property is situated in Kirkbymoorside, it is located approximately 28.03 km from Upper Helmsley. Penny's Place sleeps a maximum of 2 people and the low season price starts from 155. |
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| Vivers Mill Cottage |
| Pickering, Yorkshire and Cleveland |
| Sleeps: 2 Low Price: 175 High Price: 650. |
| This property is situated in Pickering, it is located approximately 28.62 km from Upper Helmsley. Vivers Mill Cottage sleeps a maximum of 6 people and the low season price starts from 175. |
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| Stable Cottage 2 |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 6 Low Price: 325 High Price: 450. |
| This property is situated in Kirkbymoorside, it is located approximately 29.24 km from Upper Helmsley. Stable Cottage 2 sleeps a maximum of 4 people and the low season price starts from 325. |
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| Stable Cottage 1 |
| Kirkbymoorside, Yorkshire and Cleveland |
| Sleeps: 4 Low Price: 325 High Price: 450. |
| This property is situated in Kirkbymoorside, it is located approximately 29.25 km from Upper Helmsley. Stable Cottage 1 sleeps a maximum of 4 people and the low season price starts from 325. |
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