Popular Features
Sleeps
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Popular Cottages
- The Gardeners Cottage Richmond
- Barforth Hall Dairy
- Dragonfly
- Wren
- Box Tree Escapes
- Box Tree Farm House
- Farmstead Cottage At Bland Close Farm
- Wooden Hare
- Sykelands Cottage
- Foxes Den
- Owl At Grace View
- Fox's Den
- The Old Wagon Shed
- Low Shipley Cottage
- Springhill Farm Cottage
- The Dairy
- Cass Lodge in
- Keepers Hide at Wuthering Huts
- Butterfly Lodge
- The Pump House
- Fishermans Cabin
- Poppy Cottage at Hoxne Cottages
- King's Cottage
- The Milking Parlour
- Lovesome Cottage
- The Granary
- 16 Badgers Retreat
- The Leveret
- Wishing Well Lodge
- Bolster Moor View Golcar
Middleham Holiday Cottages
Our collection of Middleham holiday cottages puts you right in the heart of Wensleydale's racing heritage. This historic North Yorkshire market town is home to Middleham Castle where Richard III once lived! You'll discover cobbled streets lined with traditional stone buildings and working racing stables that train champion racehorses.
Perfect for groups, couples and families seeking an authentic Yorkshire Dales stay. Browse our cottage rental options including properties with hot tubs and glamping lodge alternatives. Explore the dramatic waterfalls at Aysgarth, walk to Bolton Castle or watch the gallops from Middleham Low Moor. The surrounding countryside offers exceptional hiking across ancient moorland trails.
Visitor Rating
5
- Exceptional quality throughout
- Covered hot tub with speakers
- Perfect village location
- Historical 1720 stone building
- Fully equipped luxury kitchen
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Visitor Rating
4.9
- Hot tub with amazing views
- Games room with multi-game table
- Walks from the doorstep
- Dog-friendly with enclosed garden
- Super-fast fibre broadband
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Visitor Rating
4.3
- Wood-fired hot tub
- Dog-friendly Yorkshire Dales location
- Walks from the doorstep
- Cosy wood burner
- Spacious comfortable bedrooms
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Visitor Rating
4.8
- Luxury barn with stunning views
- Private hot tub and sauna
- Pool table for entertainment
- Direct footpath access
- Complete peace and privacy
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Visitor Rating
4.9
- Luxury award-winning holiday home
- Private hot tub in enclosed garden
- Three bedrooms with en-suite bathrooms
- Perfect Yorkshire Dales location
- Beautifully designed with high-end features
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Visitor Rating
4.9
- Luxury log cabin with hot tub
- Stunning Yorkshire Dales views
- Dog-friendly with enclosed garden
- Super king bed with quality linens
- Multi-purpose games table
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Visitor Rating
4.9
- Private hot tub
- Spotlessly clean throughout
- Dog washing station
- Cosy wood burner
- Stunning Yorkshire Dales location
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- Private hot tub luxury
- Adults only romantic retreat
- Cosy woodburning stove atmosphere
- Yorkshire Dales parkland setting
- Tennis court access included
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Visitor Rating
4.7
- Private hot tub
- Peaceful wildlife-rich setting
- Two comfortable double bedrooms
- Close to Yorkshire Dales
- Modern open-plan living space
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Visitor Rating
4.4
- Comfortable holiday accommodation
- Peaceful location
- Hot tub relaxation
- Well-equipped interior
- Perfect countryside retreat
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Visitor Rating
5
- Private hot tub
- Dog friendly accommodation
- Yorkshire Dales location
- Modern open-plan living
- Close to historic Richmond
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Visitor Rating
4.8
- Private hot tub
- Spotlessly clean lodge
- Peaceful countryside setting
- Fully equipped modern kitchen
- Perfect couples' retreat
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Visitor Rating
5
- Private wood-fired hot tub
- Stunning countryside views
- Grade II listed building
- Luxury boutique styling
- Wildlife watching opportunities
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Visitor Rating
4.8
- Wood-fired hot tub with garden views
- Luxury wet room with monsoon shower
- Walking paths from the doorstep
- Fresh welcome pack on arrival
- Peaceful Yorkshire Dales location
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Visitor Rating
4.9
- Private hot tub and sauna
- Super comfortable king bed
- Helpful and friendly owners
- Perfect Yorkshire Dales location
- Fully equipped luxury kitchen
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Visitor Rating
4.1
- Private hot tub overlooking Bedale Beck
- Cosy woodburning stove
- Two comfortable bedrooms
- Award-winning Yorkshire Dales property
- Walking distance to local pub
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Visitor Rating
4.5
- Private hot tub
- Woodburning stove
- Character features
- Spacious for 8 guests
- Near Yorkshire Dales attractions
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Visitor Rating
4.7
- Private hot tub in secluded garden
- Between two stunning national parks
- Cosy cottage with character features
- Short walk to local pub
- Welcome hamper on arrival
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Visitor Rating
4.2
- Private hot tub at 40°C
- Three comfortable bedrooms
- Walking distance to local pub
- Welcome pack with essentials
- Great Yorkshire Dales location
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Visitor Rating
5
- Private hot tub and sauna
- Spotlessly clean accommodation
- Short walk to Richmond
- Superking bed with TV
- Peaceful Yorkshire Dales location
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Visitor Rating
4.9
- Private hot tub in walled garden
- Grade II-listed luxury townhouse
- Central Richmond location
- Wood burner for cosy evenings
- Dog-friendly accommodation
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Visitor Rating
4.6
- Private hot tub in enclosed garden
- Short walk to Richmond town center
- Woodburning stove in cozy lounge
- Dog-friendly with secure garden
- Historic property with modern comforts
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Visitor Rating
4.8
- Private hot tub
- Ten-minute walk to Richmond centre
- Enclosed garden for dogs
- Welcome treats on arrival
- Light-filled kitchen with modern appliances
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Visitor Rating
4.7
- Private hot tub
- King-size bed with freestanding bath
- Dog-friendly with secure outdoor space
- Pub and shop within walking distance
- Perfect Yorkshire Dales location
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Visitor Rating
5
- Private hot tub with countryside views
- Luxury king-size bed with freestanding bath
- 5-star amenities throughout
- Dog-friendly with shared paddock
- Cosy wood burner for winter evenings
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Visitor Rating
5
- Luxury cottage with hot tub
- Dog-friendly with enclosed garden
- Wood burner for cozy evenings
- Walking distance to local pubs
- High-quality throughout
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Visitor Rating
3.9
- Hot tub for relaxing
- Self-catering accommodation
- Private holiday lodge
- Comfortable home from home
- UK holiday destination
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Visitor Rating
4.9
- En-suite bedrooms with luxury baths
- Hot tub with countryside views
- Walking distance to pub
- Perfect for large groups
- Stunning Yorkshire Dales location
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Visitor Rating
4.4
- Private hot tub with views
- Three en-suite bedrooms
- Walking trails from doorstep
- 5 minutes from Richmond
- Luxurious barn conversion
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Visitor Rating
4.1
- Private wood-burning hot tub
- Two luxury four-poster beds
- Enclosed courtyard with BBQ
- Perfect Yorkshire Dales location
- Open fire in stone fireplace
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Explore more of Yorkshire
Popular towns and villages in and around Middleham
Addingham Arncliffe Askrigg Aysgarth Bagby Bainbridge Bedale Bempton Beverley Bishop Monkton Bishop Wilton Brandesburton Bridlington Brierley Burlington Burnsall Carlton Catterick Cayton Cononley Cottingham Coxwold Denholme Doncaster Driffield Dunford Bridge Easingwold East Ayton Filey Flamborough Folkton Giggleswick Glaisdale Grassington Great Ayton Guisborough Harewood Harrogate Haworth Hellifield Helmsley Heptonstall Hetton Hinderwell Holmfirth Hopton Hornby Hornsea Hovingham Huddersfield Hunmanby Ilkley Ingleton Keighley Kirby Hill Kirkbymoorside Knaresborough Knayton Lealholm Leeds Leyburn Lofthouse Long Preston Lothersdale Malham Malton Marsden Masham Mickleton Middleton Mulgrave Muston Mytholmroyd Nawton Norton Nunnington Oakworth Otley Oxenhope Pateley Bridge Pickering Pocklington Ravenscar Rawdon Redcar Reeth Richmond Ripon Ripponden Robin Hood's Bay Romaldkirk Runswick Bay Saltaire Sandsend Scarborough Seamer Sedbergh Selby Settle Shepley Sheriff Hutton Silsden Skipsea Skipton Sleights Slingsby Sowerby Sowerby Bridge Staithes Stanley Stokesley Sutton Thornhill Threshfield Todmorden Ugthorpe Wakefield Walkington Wentworth West Tanfield Wetherby Whitby Withernsea Wyke York