Winston Holiday Cottages

Your Winston, Durham search returned 113 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

  • 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


for 7 nights £696

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Semi-detached, luxury barn conversion. Beams and trusses and multi-fuel stove. Well-equipped and comfortable. Good base for Northern Dales and County Durham. Barnard Castle 10 miles. (Ref. 920252)

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


for 7 nights £321

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £562

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    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)

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


for 7 nights £358

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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)

  • Wi-fi
  • 5% off - Wed 1st Apr to 30th Jun 2026


for 7 nights £383

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A stone-built terraced cottage resting on the outskirts of Richmond. Pet-friendly. Off-road parking. Barnard Castle 15.5 miles. (Ref. 1053055)

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


for 7 nights £409

  • 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 £466

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    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 £397

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

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


for 7 nights £354

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Traditional stone cottage near Staindrop. Beautiful rural location. Underfloor heating. Panoramic views. Comfortable family accommodation. Ideal walking, touring. Barnard Castle 5 miles. (Ref. 16414)

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


for 7 nights £461

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £430

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A fantastic four-bedroom semi-detached barn conversion resting in Marwood, Durham. Pet-friendly. Dale views. Hot tub. Original features. Off-road parking. Smart TVs. Staindrop 8.8 miles; Darlington 20.5 miles; Richmond 20.6 miles. (Ref. 16526)

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


for 7 nights £986

  • Sleeps6
  • Bedrooms3
  • PetsNo

    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
  • 10% off - Mon 1st Jun to 30th Jun 2026


for 7 nights £847

  • 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
  • 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 £522

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A delightful ground floor apartment settled in the historic town of Barnard Castle in County Durham. Pet friendly. Character. Washing machine. Staindrop 6.4 miles; Richmond 15.6 miles; Darlington 16.3 miles. (Ref. 1081145)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights £463

Last booked 3 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

  • Wi-fi
  • Off-road parking


for 7 nights £351

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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


for 7 nights £4099

  • Sleeps8
  • Bedrooms4
  • PetsYes

    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)

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


for 7 nights £915

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Immaculate, detached property in a quiet street near the centre of Darlington. Contemporary, spacious accommodation. Close to restaurants, pubs and railway attractions. Short drive to market towns of Richmond and Barnard Castle. Good touring base. (Ref. 920812)

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


for 7 nights £421

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

1 Kyles Yard is a charming cottage in Barnard Castle, County Durham, boasting off-road parking and a pet-friendly policy. Staindrop 5.3 miles; Richmond 15.6 miles; Darlington 15.4 miles; Durham 24 miles. (Ref. 1183253)

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


for 7 nights £405

Last booked yesterday
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