Winston Holiday Cottages

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Your Winston, Durham search returned 102 cottages

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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 £363

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

An attractive stone-built, detached cottage set in a secluded, pretty valley on the edge of woodland. Single-storey cottage, open plan living area. Public footpaths from doorstep. Barnard Castle 6 miles. (Ref. 21469)

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


for 7 nights £253

Last booked 2 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A lovely single-storey cottage next to the owner's home in East Layton, near Eppleby, North Yorkshire. Woodburning stove. Open-plan. Romantic. Off-road parking. Patio. Richmond 7.5 miles; (Ref. 1072404)

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


for 7 nights £422

  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Peace Cottage is a beautiful, pet-friendly cottage near Langton in Durham, boasting a woodburning stove, off-road parking, and stunning countryside views. Darlington 9.3 miles; Barnard Castle 9.7 miles; Richmond 15.4 miles; Durham 19.4 miles. (Ref. 1170306)

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


for 7 nights £541

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A contemporary three-bedroom holiday home resting in Barnard Castle, Durham. Near Yorkshire Dales National Park. Stylish. Pet-friendly. Close to amenities. Staindrop 5.5 miles; Richmond 15.5 miles; Darlington 15.5 miles; Durham 24.2 miles. (Ref. 1107098)

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


for 7 nights £584

Last booked 3 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Modern detached brick-built bungalow on edge of popular market town of Richmond. Comfortable accommodation with sun-trap garden area. Barnard Castle 10 miles. (Ref. 249)

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


for 7 nights £345

Last booked 2 days ago
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Tithe Barn is a superb, detached Grade II listed property resting in Brignall, Durham. Woodburning stove. Off-road parking. Enclosed garden. Pet-friendly. Staindrop 10.2 miles; Richmond 12.6 miles; Darlington 19.4 miles. (Ref. 1094080)

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


for 7 nights £974

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A beautifully converted barn 4 miles from the North Yorkshire town of Richmond. Open-plan. Exposed beams. En-suites. Countryside views. Richmond 3 miles. Barnard Castle 11 miles. (Ref. 935175)

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


for 7 nights £633

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A Grade II listed terraced cottage in the village of Melsonby. Large enclosed garden. Woodburning stove. Character features. Richmond 5.7 miles; Darlington 8.3 miles; Barnard Castle 12.8 miles. (Ref. 1020656)

  • Wi-fi
  • Dishwasher


for 7 nights £619

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £710

  • 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
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A luxury cottage in the village of Butterknowle. Modern bathroom. Open plan. Multi-fuel stove. WiFi. Close to Hamsterley Forest and surrounding area. Barnard Castle 10 miles. (Ref. 920251)

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


for 7 nights £318

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This second-floor, two-bedroom apartment sits in the heart of Barnard Castle, Durham. Pet-friendly. Close to amenities. Open-plan. Staindrop 6.1 miles; Richmond 14.9 miles; Darlington 16 miles; Durham 24.8 miles. (Ref. 1078125)

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


for 7 nights £384

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A traditional stone cottage in the village of Cotherstone, Durham. Original features. Romantic dwelling. Pet-friendly. Last-minute and weekend breaks. Outstanding surroundings. Barnard Castle 4.2 miles; Newbiggin 9.2 miles; Bishop Auckland 18.9 miles. (Ref. 1058422)

  • Wi-fi
  • Dishwasher


for 7 nights £505

Last booked yesterday
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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 £466

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Ivy Cottage is a delightful, pet-friendly house resting near an array of attractions in Richmond, Yorkshire, boasting an enclosed garden and Smart TV. Leyburn 9.3 miles; Barnard Castle 14.6 miles; Middlesborough 28.2 miles; Hartlepool 36.6 miles. (Ref. 1166505)

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


for 7 nights £438

Last booked 2 days ago
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  • 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
  • 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


for 7 nights £847

  • Sleeps5
  • Bedrooms2
  • PetsNo

    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 £497

Last booked yesterday
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  • 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 £987