Middleham Cottages

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Your Middleham, North Yorkshire search returned 132 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

A pretty, semi-detached bungalow sitting in Middleham in the Yorkshire Dales National Park, North Yorkshire. Close to amenities. Smart TV. Ground-floor living. Leyburn 2 miles; Richmond 11.7 miles. (Ref. 1077485)

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

7 nights from £434

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

A charming wooden lodge set on a complex within the village of Tunstall, North Yorkshire. Pet-friendly. Decking. Off-road parking. Hispwell 2.8 miles; Richmond 4.7 miles. (Ref. 1114534)

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

7 nights from £379

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes
  • Sykes rating

A stone-fronted ground-floor apartment resting in Masham, North Yorkshire. Near Yorkshire Dales National Park. Original features. Open-plan. Pet-friendly. Close to amenities. Bedale 6 miles; Ripon 9.6 miles; Northallerton 14.6 miles. (Ref. 1051043)

  • Wi-fi
  • Ground floor bedroom
  • £356 off - Mon 19th Sep to 26th Sep 2022

  • £380 off - Mon 3rd Oct to 10th Oct 2022

7 nights from £354

  • Sleeps3
  • Bedrooms2
  • PetsYes
  • 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 £311

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    Excellent

  • 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 £352

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    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 £407

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • 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 £348

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A contemporary wooden lodge set on a wonderful complex within the village of Tunstall, North Yorkshire. Open-plan living. Electric fire. Private Veranda. Richmond 4.8 miles; Northallerton 14.7 miles; Harrogate 32.7 miles. (Ref. 1105610)

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

7 nights from £379

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A pretty semi-detached cottage situated in Leyburn, North Yorkshire. Off-road parking. Enclosed garden. Woodburning stove. Close to amenities. Richmond 9.1 miles; Darlington 21.8 miles. (Ref. 1014717)

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

7 nights from £480

Last booked 6 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Very good

  • Sykes rating

A delightful Grade II listed terraced cottage in the popular market town of Middleham. Set over three floors with original exposed beams and stonework, perfect for exploring the Yorkshire Dales. Leyburn 2.5 miles. (Ref. 943074)

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

7 nights from £405

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A lovely stone annex cottage resting on the outskirts of Middleham, North Yorkshire. Woodburning stove. Romantic. Near to Yorkshire Dales National Park. Leyburn 1.3 miles; Richmond 10.5 miles. (Ref. 995948)

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

7 nights from £348

  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.7

    Good

  • 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

7 nights from £310

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Excellent

  • Sykes rating

A quaint mid-terrace cottage resting within the centre of Middleham. Close to all amenities. WiFi. Leyburn 2.1 miles; Richmond 11.3 miles. (Ref. 1060887)

  • Wi-fi
  • Dishwasher
  • Baby-friendly
  • 15% off - Fri 12th Aug to 26th Aug 2022

7 nights from £380

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

An elevated, luxury lodge resting in Tunstall near Catterick, North Yorkshire. Off-road parking. Close to amenities. Decked terrace. Open-plan. Countryside views. Richmond 4.7 miles; Northallerton 14.7 miles; Harrogate 34.5. (Ref. 1105641)

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

7 nights from £420

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.3

    Good

  • 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 £422

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2

    Good

  • Sykes rating

A lovely stone-built terraced cottage in the market of Leyburn. Character and charm throughout. Romantic bolthole. Good touring base. Richmond 9.1 miles; Darlington 21.6 miles. (Ref. 1054524)

  • Wi-fi

7 nights from £348

Last booked 6 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Very good

  • Sykes rating

Stunning, terraced cottage sits in the Yorkshire town of Middleham. Dog-friendly. Near Yorkshire Dales. Open fire. (Ref. 969891)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £455

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Excellent

  • 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 £393

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6

    Very good

  • 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 £341

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Excellent

  • Sykes rating

An exquisite cottage nestled on the edge of the Yorkshire Dales National Park. Open-plan. Two woodburning stoves. Brilliant walking routes. Leyburn 2 miles. (Ref. 1012081)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £460

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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 a 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.

Whatever your tastes and hobbies, you will find plenty of things to do on a holiday in Middleham. Book your self-catering accommodation today by calling one of our travel experts on 01244356666,