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Middleham Cottages

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Your Middleham, North Yorkshire search returned 124 cottages

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7 nights from £387

  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Outstanding barn conversion on the outskirts of pretty Middleham. Beautiful long-distance views and just a short walk to the market square. Super king-size beds, en-suites, woodburner. Leyburn 2.2 miles. (Ref. 905078)

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

7 nights from £1073

  • 2 Guests
  • 1 Bedroom
  • Pets No

    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

Last booked yesterday
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  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.8

    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

  • 3 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    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 £415

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    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

7 nights from £461

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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

  • 7 Guests
  • 4 Bedrooms
  • Pets No

    5.0

    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
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £659

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.6

    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

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    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 £749

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.6

    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

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A homely Grade II listed cottage in the centre of Richmond market town in North Yorkshire. Courtyard. Pet friendly. WiFi. Colburn 3.2 miles; Leyburn 8.5 miles; Darlington 12.6 miles. (Ref. 1054760)

  • Wi-fi
  • Washing machine

7 nights from £412

  • 8 Guests
  • 4 Bedrooms
  • Pets No

    Sykes Rating

St Edmunds House is a charming stone cottage in the charming North Yorkshire village of Crakehall, near the Yorkshire Dales and boasting a private hot tub. Bedale 2.1 miles: Leyburn 8.7 miles. (Ref. 1171075)

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

7 nights from £815

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.5

    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 £448

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.8

    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

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    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 £540

Last booked 2 days ago
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7 nights from £458

  • 2 Guests
  • 1 Bedroom
  • Pets No

    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 £553

Last booked 5 hours ago
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  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.3

    Sykes Rating

Finnbars Lodge is a charming, single-storey holiday lodge resting in the village of Hipswell in North Yorkshire welcoming pets and with a Smart TV. Scotton 2.2 miles; Richmond 4.7 miles. (Ref. 1166077)

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

7 nights from £451

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    Sykes Rating

River Dance Cottage is a wonderful home sitting pretty in the Yorkshire Dales National Park in Aysgarth near West Burton, enjoying serene river views. Leyburn 7.4 miles; Hawes 9.3 miles. (Ref. 1170123)

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

7 nights from £539

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.