Middleham Cottages

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Middleham Cottages

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Your Middleham, North Yorkshire search returned 132 cottages

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Map View
A stone house with windows and wooden doors surrounded by greenery and a garden at The Summer Palace in Middleham Wensleydale
12
Middleham, Wensleydale, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

A wonderful ground floor, detached cottage set in a walled garden just off the village square in Middleham, perfect for couples. En-suite bedroom. Woodburner. WiFi. Leyburn 2.2 miles. (Ref. 904813)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £392

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An outdoor patio with wooden table and chairs in front of a round stone building with a wooden door and small windows at The Round House in Middleham Wensleydale
14
Middleham, Wensleydale, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

A perfect roundhouse cottage in a walled garden in the centre of Middleham, just perfect for a romantic trip! WiFi. Woodburner. Leyburn 2.2 miles. (Ref. 904812)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £387

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A stone castle courtyard with arched garage doors and outdoor seating at Catherine Parrs Sewing Room in Snape near Bedale
New property
30
Snape near Bedale, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    Sykes Rating

Catherine Parrs Sewing Room is a romantic and historic first-floor apartment in a castle tower near Bedale, North Yorkshire, with a 14th-century staircase. Northallerton 11.2 miles; Darlington 24 miles; Wensleydale 28.1 miles. (Ref. 1155296)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £724

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An outdoor area with stone walls and furniture at Poppy's Footprint in Leyburn
New property
20
Middleham. Wensleydale, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    Sykes Rating

Poppy's Footprint is a fantastically unique property in Middleham, North Yorkshire, boasting an open-plan living space and a bedroom with an en-suite. Leyburn 2.3 miles; Richmond 11.4 miles. (Ref. 1172220)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £392

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A stone cottage with arched windows and doors a gravel driveway and plants at The Cart House in Snape near Bedale
25
Snape near Bedale, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

The Carthouse, a delightful bungalow resting in the village of Snape near Bedale in North Yorkshire. Near National Park. Off-road parking. Single-storey. Northallerton 11.8 miles; Darlington 24 miles; Wensleydale 26.2 miles. (Ref. 1155863)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £537

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Exterior stone wall of a cottage with a green door and window below stairs leading to a small balcony with table and chairs at In & Out Cottage in Middleham
39
Middleham, North Yorkshire, DL8
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

Wensleydale cottage off market square in Middleham. Upside down accommodation. Woodburner, beams and stonework. Amenities on doorstep. Ideal romantic location. Leyburn 2.5 miles. (Ref. 972733)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £406

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Stone exterior of a cottage with white door and window a black drainpipe and a light blue wooden gate with lattice design and a tree behind a stone wall at Olive Cottage in Richmond
16
Richmond, North Yorkshire, DL10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6

    Sykes Rating

A delightful stone-built, semi-detached cottage just two minutes from the centre of Richmond. King-size bed, off road parking, enclosed garden. Ideal for a couple. Barnard Castle 10 miles. (Ref. 955196)

  • Wi-fi
  • Off-road parking

7 nights from £357

Last booked 2 days ago
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A stone cottage with a light green door and windows surrounded by gravel and plants at Ivy Cottage in Grewelthorpe near Masham
22
Grewelthorpe near Masham, North Yorkshire, HG4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

A superb stone-built detached cottage. Uninterrupted countryside views, open plan living area with woodburning stove. Pub nearby. Walks from the doorstep. Masham 3 miles. (Ref. 942580)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly

7 nights from £424

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The exterior of a building with cream walls and six windows with white frames and black sills and a covered parking area at 3 Kings Mews in Richmond
30
Richmond, North Yorkshire, DL10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Sykes Rating

A well-located first-floor apartment resting in the heart of Richmond, North Yorkshire. Designated parking. Close to amenities. Pet free. Open-plan. Leyburn 9 miles; Barnard Castle 15 miles. (Ref. 1102415)

  • Wi-fi
  • Washing machine

7 nights from £351

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A stone house with a dark roof and two arched windows a tree in front and a stone pathway on a grassy lawn at Woodland View in Richmond
28
Richmond, North Yorkshire, DL10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A contemporary first-floor apartment resting on the outskirts of Richmond in North Yorkshire. Open-plan. Private hot tub. Romantic. Darlington 14.6 miles; Northallerton 17.3 miles. (Ref. 1070889)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from £603

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Stone cottage with white windows and doors and a small garden with flowers and outdoor furniture at Cartmel Cottage in Middleham
12
Middleham, North Yorkshire, DL8
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6

    Sykes Rating

Lovely terraced cottage close to market square and amenities in Middleham. Cosy romantic retreat with beamed ceiling, open plan living area and cottage garden. Leyburn 2.5 miles. (Ref. 929525)

  • Wi-fi
  • Washing machine

7 nights from £366

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A stone house with a bay window and a garage with a green door at 10 Old School Close in West Witton
31
West Witton, Yorkshire Dales, DL8
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

Stone-built, semi-detached cottage nestled in a quiet cul-de-sac, in the small village of West Witton. Off-road parking. Open fire. Yorkshire Dales National Park. (Ref. 989427)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £458

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A stone cottage with multiple white-framed windows and a white door beside a narrow road with grass and trees at Hobson's Cottage in Fremington near Reeth
30
Fremington near Reeth, Yorkshire Dales, DL11
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

Charming stone-built semi-detached cottage in the hamlet of Fremington, a short walk from Reeth. Hillside position. Lovely views. Yorkshire Dales National Park. Reeth 0.5 miles. (Ref. 977819)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £480

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The exterior of a stone cottage with a white door surrounded by potted plants and ivy at Middle Cottage in Middleham
31
Middleham, North Yorkshire, DL8
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

A delightful mid-terrace cottage with spacious accommodation. The cottage is a real delight with lots of character and contemporary styling. Great walks from the doorstep. Pets welcome. Leyburn 2.5 miles. (Ref. 929028)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £410

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A stone courtyard with green door and gate and metal table and chairs at Wedgewood Cottage in Middleham
15
Middleham, North Yorkshire, DL8
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

A stone built mews cottage, resting in the town of Middleham, on the outskirts of the Yorkshire Dales National Park. Open fire. Enclosed garden. Close to amenities. Leyburn 2.4 miles; Richmond 11.7 miles. (Ref. 1024465)

  • Wi-fi
  • Dishwasher

7 nights from £362

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The exterior of a stone cottage with a green door and two windows at Myrtle Cottage in West Witton near Leyburn
28
West Witton near Leyburn, Yorkshire Dales, DL8
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

A stone-built, terraced cottage with a lovely garden on the outskirts of West Witton. Woodburner. Leyburn 3.7 miles. (Ref. 906028)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £381

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A living room with a grey sectional sofa multiple cushions a round wooden coffee table a rug a fireplace with logs and a mounted television at The Old Store 2 Alpine Terrace in Reeth
28
Reeth, Yorkshire Dales, DL11
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.3

    Sykes Rating

A well-positioned two-bedroom cottage, resting in the heart of Reeth, in North Yorkshire. Pet-friendly. Stylish. Close to amenities. Within Yorkshire Dales National Park. Leyburn 8 miles; Richmond 11.2 miles; Barnard Castle 14.2 miles. (Ref. 1067595)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £372

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A stone cottage exterior with wooden framed windows and a small covered entrance at Pollard Cottage in Kirkby Fleetham near Northallerton
19
Kirkby Fleetham near Northallerton, North Yorkshire, dl7
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.5

    Sykes Rating

This delightful holiday cottage rests in Kirkby Fleetham near Northallerton, North Yorkshire. Pet-friendly. Woodburning stove. Northallerton 8.6 miles; Richmond 11.3 miles; Thirsk 16 miles. (Ref. 1065303)

  • Wi-fi
  • Off-road parking
  • Washing machine

7 nights from £395

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A wooden lodge with a fenced deck and gravel path outside at 10 Poppy Lodge in Tunstall near Catterick North Yorkshire
31
Tunstall near Catterick, North Yorkshire, North Yorkshire, DL10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

10 Poppy Lodge is a fabulous detached lodge that rests in Tunstall, Richmondshire. Open-plan. Enclosed decking. Pet-friendly. Smart TV. Richmond 4.7 miles; Northallerton 14.7 miles; Harrogate 34.5 miles. (Ref. 1149161)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £422

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Stone building with green doors and windows with grass and bushes in front at Prospect Barn in West Witton
25
West Witton, Yorkshire Dales, DL8
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

Prospect Barn is a pleasant, single-storey, and pet-friendly cottage located in West Witton, North Yorkshire, boasting an enclosed garden and Smart TV. Leyburn 3.8 miles; Middleham 5 miles; Hawes 12.8 miles; Richmond 12.8 miles; Darlington 28.7 miles. (Ref. 1171484)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £437

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Map View

If you are looking for a fascinating stay in a historical centre, look no further than a selection of holiday cottages to rent in Middleham. The small market town was once regarded as the 'Windsor of the North' due to its royal heritage, boasting a twelfth century castle that was once the childhood home of the infamous King Richard III, which also possesses the North of England's largest castle keep.

Discover Middleham's long-standing equestrian history

Explore the market town's quaint, winding streets, wander through the cobbled market squares all the while admiring the beautiful Georgian and Victorian architecture. The sport of Horse racing has long been linked to the town of Middleham. It was in 1773 that the first documented reference involving racehorses at Middleham was recorded, in the years since it has become synonymous with breeding and training racehorses and is still seen as one of the top training centres in the UK.

For 360-degree views across the Yorkshire Dales, climb up to the remains of Middleham Castle, a splendid medieval keep and once home of Richard III. Equally splendid is the outlook from Leyburn Shawl, a stunning limestone escarpment that was the escape route of Mary Queen of Scots as she fled from Bolton Castle - another medieval fortress not to miss.

Take a tour around the famous training centre or visit some of the charming town's art galleries, tearooms and pubs. Other nearby attractions include real ale breweries, historic sites like Jervaulx Abbey, the gardens of Constable Burton Hall, not to mention the spectacular waterfalls of Aysgarth and West Burton. You can also venture to the nearby towns of Northallerton and Ripon.

Whatever your tastes and hobbies, you will find plenty of things to do on a holiday in Middleham. If you still haven't found your perfect cottage, check out these dog-friendly cottages in the Yorkshire Dales.