Middleham Cottages

Your Middleham, North Yorkshire search returned 153 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.8

    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)

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


for 7 nights From £478

Last booked today
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Holiday Park

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • 5% off - Sat 5th Sep to 3rd Oct 2026


for 7 nights From £446

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Fleetwood is a stylish single-storey retreat in Tunstall near Catterick, North Yorkshire, with stunning countryside views, and easy access to walks. Richmond 6 miles; Northallerton 13.5 miles; Harrogate 33.3 miles (Ref. 1193858)

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


for 7 nights From £482

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyNo

    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 From £521

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

2 West View, a pleasant pet-friendly house nestled in Richmond, North Yorkshire, boasts proximity to Yorkshire Dales National Park and local amenities. Leyburn 8.8 miles; Barnard Castle 14.3 miles. (Ref. 1202289)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • 10% off - Sat 29th Aug to 11th Oct 2026


for 7 nights From £511

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Poppy's Footprint is a fantastically unique property in Middleham, North Yorkshire, boasting an open-plan living space and a bedroom with an en-suite. Leyburn 2.3 miles; Richmond 11.4 miles. (Ref. 1172220)

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


for 7 nights From £391

Holiday Park

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    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)

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


for 7 nights From £421

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £508

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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


for 7 nights From £449

Last booked yesterday
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Holiday Park

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From £484

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights From £677

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    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


for 7 nights From £406

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly


for 7 nights From £366