Middleham Cottages

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Your Middleham, North Yorkshire search returned 128 cottages

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  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • 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

  • 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

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

  • 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

  • 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
  • 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
  • 10% off - Wed 1st Oct to 1st Nov 2025

7 nights from £442

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Rosemary Cottage is a splendid pet-friendly property near the town of Leyburn, North Yorkshire, boasting a woodburning stove in the sitting room. Richmond 11.6 miles. (Ref. 1177942)

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

7 nights from £397

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    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

7 nights from £463

  • 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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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    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 £386

Last booked yesterday
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  • 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

7 nights from £387

  • 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
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine

7 nights from £378

Last booked yesterday
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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

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • 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 £431

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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

7 nights from £563

  • 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

  • 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
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £659

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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 £526

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    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 £392

  • 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

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.