Middleham Cottages

Your Middleham, North Yorkshire search returned 154 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps8
  • Bedrooms4
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Beningborough is an outstanding barn conversion near Middleham, North Yorkshire, with a woodburning stove, beautiful views, and four en-suite bedrooms. Leyburn 2.3 miles; Richmond 11.4 miles. (Ref. 1193569)

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


for 7 nights £1087

  • 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


for 7 nights £788

  • 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


for 7 nights £445

  • 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


for 7 nights £812

Last booked 8 hours ago
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  • Sleeps7
  • Bedrooms4
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A traditional, three-storey terraced house situated in Leyburn, North Yorkshire. Enclosed garden. Close to amenities. Beautiful views. Richmond 9.4 miles. (Ref. 1084963)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Mon 1st Jun to 31st Dec 2026


for 7 nights £624

Holiday Park

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Badgers Retreat - Two Dales is a fabulous pet-friendly lodge near Hipswell, boasting a hot tub, countryside views and an open-plan living space to enjoy. Scotton 2.2 miles; Richmond 4.7 miles. (Ref. 1181883)

  • Wi-fi
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights £602

Last booked 2 days ago
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  • 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


for 7 nights £601

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Eastend Cottage, a charming pet-friendly cottage, over three floors, in West Witton, North Yorkshire, boasts lovely views, and a woodburning stove. Middleham 4.9 miles; Hawes 12.9 miles; Leyburn 3.5 miles. (Ref. 1175732)

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


for 7 nights £605

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

An outstanding Grade II listed, end-terraced cottage in the delightful market town of Middleham. Set within a stone's throw of King Richard’s castle. Original exposed beams and stone floors. Perfect for exploring the Yorkshire Dales! Leyburn 2.5 miles. (Ref. 928299)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Sky TV


for 7 nights £782

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • 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


for 7 nights £467

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Delightful stone-built converted barn in quiet position on edge of the pretty village of Carperby, in Upper Wensleydale. Aysgarth Falls 1 mile; Castle Bolton 2 miles. (Ref. 567)

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


for 7 nights £331

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Baytree Cottage rests in Richmond, North Yorkshire, Multiple Winner of the Perfect 10 Rating Award. Free parking. Pet-friendly. Yorkshire Dales National Park 11.1 miles; Darlington 13.4 miles. (Ref. 1139017)

  • Wi-fi
  • Washing machine
  • Sky TV


for 7 nights £639

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • 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


for 7 nights £457

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A homely, stone-built cottage for six in the Yorkshire Dales village of Thornton Rust. Countryside views. Woodburning stove. Aysgarth 2 miles. (Ref. 1010391)

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


for 7 nights £461

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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


for 7 nights £349

Last booked 9 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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


for 7 nights £526

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Charming semi-detached stone cottage in Dales village of Redmire. Overlooking village green. Three bedrooms. Open fire. Ideal for walkers. Leyburn 4 miles. (Ref. 8835)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights £494

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • 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


for 7 nights £387

  • 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


for 7 nights £371

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.