Winston Holiday Cottages

Your Winston, Durham search returned 116 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

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

A charming two-bedroom cottage resting in Staindrop, North Yorkshire. Pet-friendly. Woodburning stove. Near a National Park. Open-plan. Barnard Castle 5.7 miles; Durham 18.8 miles. (Ref. 943950)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights From £442

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

This newly listed property is a historic, end terrace cottage resting in Richmond, Swaledale. Near a river. Off-road parking. Woodburning stove. Pet-friendly. Leyburn 10.3 miles; Barnard Castle 15.6 miles. (Ref. 1096626)

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


for 7 nights From £673

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

The Gate House, a delightful holiday cottage in Aldbrough St. John, Yorkshire. Smart TV. Woodburning stove. Pet-friendly. Hot tub. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1179012)

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


for 7 nights From £1282

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • 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

  • 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

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A two-bedroom, stone-fronted cottage resting in Staindrop, Durham. Close to amenities. Woodburning stove. Pet-friendly. Raby Castle 1.7 miles; Barnard Castle 5.5 miles; Durham 19 miles. (Ref. 1097522)

  • Pets go free
  • Wi-fi


for 7 nights From £354

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A former postmistress’ cottage nestled at the edge of Ravensworth, North Yorkshire. Near a National Park. Woodburning stove. Pet-friendly. Smart TV. Enclosed garden. Richmond 5.4 miles; Barnard Castle 8.9 miles; Leyburn 14.2 miles. (Ref. 1054273)

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


for 7 nights From £667

  • 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 1 hour ago
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  • Sleeps5
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

An exceptional stable conversion resting on the outskirts of Barnard Castle in North Yorkshire. Single-storey accommodation. Open-plan living. WiFi. Hot tub. Middleton in Teesdale 12.8 miles; Richmond 15 miles. (Ref. 1078952)

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


for 7 nights From £1304

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £528

  • Sleeps5
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Superb barn conversion in Gilling West. WiFi, en-suite, woodburner, garden. Spacous welcoming accommodation with beams, finished to a high standard. Pub 15 mins walk. (Ref. 934810)

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


for 7 nights From £502

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £364

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

4 Castle Terrace is a charming holiday home resting in Bowes, a quaint village in Durham. Woodburning stove. Open-plan. Pet-friendly. Smart TV. Dishwasher. Staindrop 10.2 miles; Richmond 17.5 miles; Darlington 20.6 miles; Durham 29.2 miles. (Ref. 1149455)

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


for 7 nights From £425

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

The Farm House, a charming holiday cottage resting by Aldbrough St. John, Yorkshire. Hot tub. Smart TV. Woodburning stove. Pet-friendly. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1179009)

  • Pets go free
  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £1757

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

A charming first floor apartment located in the village of Bridge End, County Durham. Views of River Tees. Barnard Castle 6 miles. (Ref. 974578)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Washing machine
  • Games room


for 7 nights From £353

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Wren Cottage is a lovely cottage in Barton, North Yorkshire, with an enclosed courtyard and a multi-fuel woodburning stove, well-positioned to amenities. Richmond 7.3 miles. Darlington 6 miles. (Ref. 1201570)

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


for 7 nights From £380

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From £915