Middleham Cottages

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Your Middleham, North Yorkshire search returned 130 cottages

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  • 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


for 7 nights $705

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A delightful stone-built, semi-detached cottage just two minutes from the centre of Richmond. King-size bed, off road parking, enclosed garden. Ideal for a couple. Barnard Castle 10 miles. (Ref. 955196)

  • Wi-fi
  • Off-road parking


for 7 nights $439

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  • 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


for 7 nights $731

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely three-bedroom cottage resting in Fremington, North Yorkshire. Pet-friendly. In a National Park. Enclosed garden. Off-road parking. Leyburn 7.5 miles; Richmond 10.6 miles; Barnard Castle 14.7 miles. (Ref. 1102914)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher


for 7 nights $810

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A stone-built terraced cottage resting on the outskirts of Richmond. Pet-friendly. Off-road parking. Barnard Castle 15.5 miles. (Ref. 1053055)

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


for 7 nights $536

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Pencroft Cottage is a fine, single-storey house located in Caperby, North Yorkshire, boasting two woodburning stoves and three en-suite bedrooms. Leyburn 7.6 miles; Middleham 9 miles; Hawes 10 miles; Richmond 14.3 miles; Darlington 30.1 miles. (Ref. 1171485)

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


for 7 nights $654

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful barn conversion close to the centre of Masham. Light and airy cottage with WiFi, a wet room and underfloor heating. Fantastic walking and cycling. Pub and shops nearby. Ripon 10 miles. (Ref. 916222)

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


for 7 nights $524

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A superb, single-storey lodge resting on the outskirts of Richmond, North Yorkshire. Hot tub. Near a National Park. Pet-friendly. Leyburn 12 miles; Barnard Castle 19.8 miles. (Ref. 1116790)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub


for 7 nights $684

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    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
  • Washing machine


for 7 nights $743

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A fabulous, two-bedroom cottage resting in Preston under Scar near Leyburn, North Yorkshire. Near National Park. Private driveway. Contemporary. Ideal for couples. Ground-floor living. Pet-friendly. Richmond 10.5 miles; Darlington 23.3 miles. (Ref. 1004125)

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


for 7 nights $619

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Hollymoor Hall Farm is a lovely, pet-friendly detached holiday home resting in the lovely town of Richmond in North Yorkshire with a woodburning stove. Leyburn 9.5 miles; Barnard Castle 14.7 miles. (Ref. 1179013)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights $1565

  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • 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 $676

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Rashierigg is an elevated, luxury lodge resting in Tunstall near Catterick, North Yorkshire, boasting off-road parking and an open-plan living space. Richmond 4.7 miles; Northallerton 14.7 miles; Harrogate 34.5. (Ref. 1105641)

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


for 7 nights $729

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A well-presented, comfortable three storey, stone-built townhouse situated on the foot of the green in Reeth. Woodburner. WiFi. Pet-friendly. Walks from the door. Leyburn 8 miles. Richmond 10 miles. (Ref. 15569)

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


for 7 nights $808

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful, reverse-level barn conversion resting in Ellingstring near Masham, North Yorkshire. Romantic. Pet-friendly. Rural. In National Park. Open-plan living. Bedale 9.7 miles; Ripon 14.3 miles; Northallerton 17.6 miles. (Ref. 1135633)

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


for 7 nights $475

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A stone-built detached cottage, a former Post Office tucked away in the Swaledale village of Marrick. First class cottage with lots of character and charm and open fires. WiFi. Pet-friendly. Reeth 3 miles. (Ref. 27237)

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


for 7 nights $681

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A striking stone-built cottage resting in Richmond, North Yorkshire. En-suites. Garden. Family-friendly. Leyburn 9.2 miles; Barnard Castle 15.3 miles. (Ref. 1078275)

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


for 7 nights $1125

  • Sleeps13
  • Bedrooms6
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A fabulous three-storey, mid-terrace holiday home resting in Reeth, Richmondshire. Woodburning stove. Pet-friendly. Enclosed garden. In Yorkshire Dales National Park. Leyburn 7.9 miles; Richmond 10 miles; Barnard Castle 14.2 miles. (Ref. 1085955)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly
  • 5% off - Sat 1st Nov to 30th Nov 2025


for 7 nights $2111

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely, single-storey barn conversion enjoying rural views in Ellingstring near Masham, North Yorkshire. In National Park. Private patio. Countryside views. Pet-friendly. Bedale 9.7 miles; Ripon 14.3 miles; Northallerton 17.6 miles. (Ref. 1135714)

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


for 7 nights $570

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Modern detached brick-built bungalow on edge of popular market town of Richmond. Comfortable accommodation with sun-trap garden area. Barnard Castle 10 miles. (Ref. 249)

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


for 7 nights $451