Middleham Cottages

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Your Middleham, North Yorkshire search returned 146 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Hayloft is a charming and pet-friendly first-floor property in Brompton on Swale, North Yorkshire, boasting countryside views and enclosed decking. Richmond 3.4 miles; Leyburn 12.2 miles; Reeth 14.1 miles; Barnard Castle 17.4 miles; Middlesbrough 30.9 (Ref. 1171958)

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


for 7 nights $517

Last booked yesterday
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  • 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 $597

  • 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 $738

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

30 Ayr Avenue, a lovely first-floor apartment resting in Colburn, North Yorkshire. Smart TV. Open-plan living space. Designated parking. En-suite. Scotton 2.2 miles; Richmond 3.7 miles. (Ref. 1138317)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $573

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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


for 7 nights $501

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Dragonfly, a lovely, single-storey lodge located in Tunstall near Hipswell in North Yorkshire, boasting a hot tub, a Smart TV, and a pet-freindly policy. Scotton 2.1 miles; Richmond 4.7 miles. (Ref. 1164432)

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


for 7 nights $776

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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


for 7 nights $655

  • 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 $470

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Pheasant Cottage is a delightful, two-bedroom holiday home resting in Hurst, North Yorkshire. Near Yorkshire Dales National Park. Countryside. Open fire. Richmond 10.4 miles; Leyburn 12.8 miles; Barnard Castle 19.4 miles; Kirkby Stephen 27.9 miles. (Ref. 1140216)

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


for 7 nights $695

  • 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 $456

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    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 $1240

  • 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 $615

Last booked yesterday
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  • Sleeps12
  • Bedrooms6
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

An 18th century grade II listed Georgian country house in the picturesque village of West Burton. Woodburners, open fire, pet-friendly. Close to village amenities. Leyburn 7 miles. (Ref. 928840)

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


for 7 nights $1947

  • 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


for 7 nights $2192

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    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 $676

  • 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 $508

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A fabulous three-bedroom cottage perched in Richmond, North Yorkshire. Hot tub. Pet-friendly. Enclosed garden. Woodburning stove. Near a National Park. Leyburn 9.2 miles; Barnard Castle 15 miles. (Ref. 1123933)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • 15% off - Fri 9th Jan to 13th Jan 2026

  • 15% off - Fri 16th Jan to 20th Jan 2026

  • 15% off - Fri 23rd Jan to 27th Jan 2026

  • 15% off - Fri 30th Jan to 3rd Feb 2026

  • 15% off - Fri 6th Feb to 10th Feb 2026


for 7 nights $915

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

An end-terrace cottage resting on the outskirts of Richmond. Pet-friendly. River close by. Barnard Castle 15.5 miles. (Ref. 1051475)

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


for 7 nights $525

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Harker View Cottage, a quaint cottage set in the ever-popular village of Reeth, North Yorkshire. Pet-friendly. Woodburning stove. Smart TV. Leyburn 7.9 miles; Richmond 11.1 miles. (Ref. 1148585)

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


for 7 nights $686

Last booked yesterday
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  • 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 $824