Winston Holiday Cottages

Your Winston, Durham search returned 116 cottages

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How reviews work

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

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Walworth Castle Lodge is a beautifully presented, pet-friendly, stone-built cottage nestled in the small village of Walworth near Darlington, Durham. Yarm 16.6 miles; Richmond 14.8 miles. (Ref. 1165778)

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


for 7 nights From £4099

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Wellington Lodge Cottage is a wonderful, single-storey annexe resting in Middleton Tyas, North Yorkshire. Near Yorkshire Dales National Park. Pet-friendly. Richmond 5.9 miles; Middlesbrough 25.2 miles. (Ref. 1145393)

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


for 7 nights From £354

Last booked 4 hours ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.3

    Good

  • Sykes rating

An inviting, single-storey cottage set amidst rolling countryside in County Durham, just outside the small village of Ingleton. Woodburning stove. Ideally positioned for touring North Pennines. Barnard Castle 7.8 miles. (Ref. 1039115)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £425

Last booked 7 hours ago
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  • 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
  • 5% off - Mon 20th Jul to 27th Jul 2026

  • 5% off - Mon 27th Jul to 3rd Aug 2026

  • 5% off - Mon 3rd Aug to 14th Aug 2026


for 7 nights From £522

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A delightful mid-terrace cottage settled just outside the centre of Richmond, North Yorkshire. Open-plan. Dog-friendly. Leyburn 9.3 miles; Barnard Castle 15.5 miles. (Ref. 1050331)

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


for 7 nights From £351

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

    4.3

    Good

  • Sykes rating

The Arches is a beautifully-presented holiday home set on a working farm in Caldwell near Eppleby in North Yorkshire. En-suite bedrooms. Countryside views. Richmond 9.7 miles. (Ref. 1147631)

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


for 7 nights From £702

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

A charming cottage in the pretty Durham village of Staindrop. Pet-friendly with woodburning stove. Perfect for touring The Durham Dales. Barnard Castle 5 miles. (Ref. 943949)

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


for 7 nights From £463

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Walworth Castle Holiday Cottage is a lovely, single-storey cottage on the grounds of the Grade I listed Walworth Castle Hotel, in Walworth near Darlington. Yarm 16.6 miles; Richmond 14.8 miles. (Ref. 1165776)

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


for 7 nights From £4099

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

26 Frenchgate is a stylish holiday home in Richmond, North Yorkshire, with a woodburning stove and hot tub. Leyburn 9.4 miles; Barnard Castle 14.9 miles. (Ref. 1177620)

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


for 7 nights From £822

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From £915

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

This superb stone cottage is based in North Yorkshire, England. WiFi. Open fire. Barnard Castle 10 miles; Leyburn 12 miles. (Ref. 999973)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From £366

Last booked 4 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

A wonderful terraced property resting in Richmond, Yorkshire. Off-road parking. Electric fire. Pet-friendly. Barnard Castle 15.5 miles. (Ref. 1053052)

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


for 7 nights From £366

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

A splendid, three-bedroom holiday home resting in Richmond, North Yorkshire. Woodburning stove. Close to amenities. Dishwasher. Leyburn 9.1 miles; Barnard Castle 15.1 miles. (Ref. 1038592)

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


for 7 nights From £657