Middleham Cottages

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Your Middleham, North Yorkshire search returned 128 cottages

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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 £540

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A charming terraced cottage resting in Reeth, North Yorkshire. Beautiful views. Close to amenities. Woodburning stove. Leyburn 8.1 miles, Richmond 11.3 miles, Barnard Castle 14.1 miles; Kirkby Stephen 22.6 miles. (Ref. 1065750)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £509

  • 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 £450

  • Sleeps5
  • Bedrooms3
  • PetsNo
  • Sykes rating

Artist’s Cottage is a delightful cottage in Richmond, North Yorkshire, well-positioned to an array of attractions and boasting a woodburning stove. Leyburn 9 miles; Darlington 13 miles; Barnard Castle 15.1 miles; Middlesborough 28.7. (Ref. 1163443)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £422

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    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

7 nights from £501

Last booked today
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This is a lovely 3 bed sleeps 5 cottage in a prominent position overlooking the village green in Reeth, North Yorkshire. Multi-fuel burner. Three bedrooms. Leyburn 8 miles; Richmond 11 miles. (Ref. 991094)

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

7 nights from £440

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A well-presented cottage in the delightful village of Fearby in North Yorkshire. Next door to Black Swan pub. In Nidderdale AONB. Open plan. Masham 2 miles. (Ref. 929673)

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

7 nights from £476

  • 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

7 nights from £461

Last booked 2 days ago
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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 £408

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Traditional Dales cottage in the centre of Reeth overlooking the village green. Private enclosed courtyard garden with three bedrooms ideal for a large family getaway. Leyburn 8 miles. (Ref. 933619)

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

7 nights from £418

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    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

  • 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 £447

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • 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 £428

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • 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
  • 10% off - Fri 27th Jun to 3rd Oct 2025

7 nights from £1072

  • Sleeps8
  • Bedrooms4
  • PetsNo
  • 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 £804

  • 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

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

17th century, Grade II listed Newbiggin cottage, close to pub in lovely National Park village. Woodburner, character accommodation, ground floor bedroom with en-suite. Leyburn 7 miles. (Ref. 4038)

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

7 nights from £552

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Magnificent detached period farmhouse near pretty West Burton. Panoramic views, open fires, exposed beams, games room, immense character. Leyburn 7 miles. (Ref. 1183)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly
  • Games room

7 nights from £582

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Stone-built, attached cottage on the edges of the Yorkshire village of Low Row, near Reeth. Garden with furniture. Wifi. Countryside views. Woodburner. Shop 3.3 miles, pub 0.1 miles. (Ref. 966210)

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

7 nights from £480

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming, reverse-level barn conversion, set rurally in Ellingstring near Masham, North Yorkshire. Pet-friendly. Countryside views. In National Park. Romantic. Characterful. Bedale 9.7 miles; Ripon 14.3 miles; Northallerton 17.6 miles. (Ref. 1135711)

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

7 nights from £376

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.