Middleham Cottages

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Your Middleham, North Yorkshire search returned 147 cottages

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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 $787

  • 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 $624

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A pretty, barn conversion resting within the village of Brompton-on-Swale. Pet-friendly. WiFi. Hot tub. Richmond 3 miles; Barnard Castle 18 miles. (Ref. 904410)

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


for 7 nights $663

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.5

    Outstanding

  • 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


for 7 nights $1136

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A charming holiday home on the outskirts of Leyburn, North Yorkshire. Dog-friendly. Close to Yorkshire Dales National Park. Secure bike storage. Enclosed garden. Richmond 8.9 miles; Bedale 11.5 miles; Northallerton 19.4 miles. (Ref. 1123727)

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


for 7 nights $490

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming townhouse situated in the village of Richmond in North Yorkshire. Wood burner. Characterful location. Three floors. Pet friendly. Barnard Castle 10 miles; Leyburn 12 miles. (Ref. 931941)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $630

Last booked yesterday
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  • 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 $668

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    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 6th Mar to 27th Mar 2026


for 7 nights $797

  • 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


for 7 nights $560

  • 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


for 7 nights $590

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A fantastic detached lodge resting in a quiet holiday park in Tunstall near Hipswell, Richmondshire. WiFi. Pet-friendly. Front decking. Off-road parking. Ground-floor living. Scotton 2 miles; Richmond 4.8 miles; Leyburn 9.9 miles. (Ref. 1083249)

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


for 7 nights $571

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A charming, three-bedroom cottage resting in Redmire near Aysgarth, North Yorkshire. Countryside views. Near National Park. Woodburning stove. Family-friendly. Castle Bolton 1 mile; Leyburn 5 miles; Hawes 12.5 miles. Sorry, Sunday check in accepted. (Ref. 1130141)

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


for 7 nights $910

  • 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 $680

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    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 $524

  • 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 $513

Last booked yesterday
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  • 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 $686

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A pretty mid-terraced cottage in the village of Low Row. Cosy cottage with two delightful bedrooms. Close to many attractions. Reeth 3 miles. (Ref. 4209)

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


for 7 nights $649

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Neddy House is a characterful, Grade II listed home resting in Grinton near Reeth, North Yorkshire. Games room. In National Park. Pet-friendly. Rural. Leyburn 7 miles; Richmond 10 miles; Barnard Castle 15.1 miles; Kirkby Stephen 23.5 miles. (Ref. 1144732)

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


for 7 nights $1766

Last booked 3 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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


for 7 nights $687

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Fairhaven is a charming, wooden lodge set on a complex within the village of Tunstall, North Yorkshire. Pet-friendly. Decking. Off-road parking. Hispwell 2.8 miles; Richmond 4.7 miles. (Ref. 1144524)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights $690