Middleham Cottages

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Your Middleham, North Yorkshire search returned 131 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A smart cottage, a former gatehouse located on the market square at Middleham. En-suites, ground floor bedrooms, woodburner, WiFi. Leyburn 2.2 miles. (Ref. 905077)

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

7 nights from £495

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Milton House is a stunning, historic property resting in the town of Middleham, North Yorkshire. Close to a shop and pub. Near National Park. Layburn 2.2 miles; Yorkshire Dales National Park 4.1 miles; North York Moors National Park 28.3 miles. (Ref. 1148753)

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

7 nights from £760

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A heart-warming cottage located in the village of Carlton-in-Coverdale, North Yorkshire. Woodburning stove. Beautiful garden with views. Close to amenities. Middleham 4.2 miles; Leyburn 5.3 miles; Hawes 15.8 miles. (Ref. 977628)

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

7 nights from £555

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A stone built cottage resting in the village of Crakehall in North Yorkshire. Enclosed garden. Rural views. Homely interior. Bedale 2 miles: Leyburn 8 miles. (Ref. 7902)

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

7 nights from £374

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A delightful former cheese factory now semi-detached holiday cottage in the centre of Masham, North Yorkshire. Woodburning stove. Close to attractions. Off-road parking. Ripon 9 miles. (Ref. 1063816)

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

7 nights from £413

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

The Cottage (B), a pleasant house located in the village of Patrick Brompton in North Yorkshire. Indoor Swimming Pool. Smart TV. Off-road parking. Bedale 3.7 miles; Middleham 7.4 miles. (Ref. 1085284)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £812

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

This delightful stone cottage is located in Middleham, North Yorkshire. WiFi. multi-fuel stove. Enclosed patio area. Leyburn 2.5 miles; Richmond 12 miles. (Ref. 1001344)

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

7 nights from £445

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • 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

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This newly listed property is a historic, end terrace cottage resting in Richmond, Swaledale. Near a river. Off-road parking. Woodburning stove. Pet-friendly. Leyburn 10.3 miles; Barnard Castle 15.6 miles. (Ref. 1096626)

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

7 nights from £590

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A superb stone barn conversion in a rural location, 0.5 miles from the hamlet of Hurst. Flagged floors, woodburning stove, contemporary kitchen and bathrooms. Very comfortable and well equipped. Walking and cycling from doorstep. Reeth 5 miles. (Ref. 20841)

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

7 nights from £435

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A characterful cottage located in the village of Newbiggin in the Yorkshire Dales. Multi-fuel stove. Ceiling beams. Charming location. Leyburn 9.2 miles; Hawes 10.8 miles. (Ref. 966542)

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

7 nights from £529

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

8 Heather Court is a beautifully-presented house located in the stunning village of West Witton in North Yorkshire. In Yorkshire Dales National Park. Middleham 5.2 miles; Leyburn 4 miles; Hawes 12.5 miles. (Ref. 1095472)

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

7 nights from £641

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • 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 £397

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This stone-built cottage can be found in Grinton near Reeth, in the Yorkshire Dales National Park. Open-plan living. Woodburning stove and underfloor heating. Private enclosed patio with countryside views. Reeth 1.2 miles; Richmond 10 miles. (Ref. 1038538)

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

7 nights from £425

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • 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

Last booked 2 days ago
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Neddy House is a characterful, Grade II listed home resting in Grinton near Reeth, North Yorkshire. Games room. In National Park. Pet-friendly. Rural. Leyburn 7 miles; Richmond 10 miles; Barnard Castle 15.1 miles; Kirkby Stephen 23.5 miles. (Ref. 1144732)

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

7 nights from £1465

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

This delightful stone barn conversion resting in Carlton, near West Witton, North Yorkshire. Woodburning stove. Enclosed garden. Pet-friendly. Off-road parking. Middleham 4.6 miles; Leyburn 5.8 miles; Hawes 16.3 miles. (Ref. 1065459)

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

7 nights from £710

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Magnolia Cottage is a beautiful, stone-built cottage resting in the village of Masham, North Yorkshire, near to a pub, shop, river, and a National Park. Ripon 9.6 miles; Yorkshire Dales National Park 14.2 miles; North York Moors National Park 19.9 miles. (Ref. 1161593)

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

7 nights from £349

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A modern, wooden lodge placed in the suburbs of Richmond in North Yorkshire. Open-plan living. En-suite. Hot tub. (Ref. 979659)

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

7 nights from £442

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.