Winston Holiday Cottages

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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

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

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


for 7 nights From £253

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £395

Last booked yesterday
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  • 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
  • £192 off - Fri 24th Jul to 31st Jul 2026

  • £137 off - Fri 28th Aug to 4th Sep 2026


for 7 nights From £599

  • 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

    4.8

    Outstanding

  • Sykes rating

Sheriff's Tower Cottage - East, a bright pet-friendly cottage in Bishop Auckland, County Durham, features private parking and a enclosed garden. Durham 10.5 miles. (Ref. 1201083)

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


for 7 nights From £402

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £409

Last booked yesterday
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  • 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 £466

  • 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 £562

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From £505

  • 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 £463

  • 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

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A wonderful, detached, 16th-century barn conversion set on a working farm in Ravensworth near Richmond, North Yorkshire. Dog-friendly. Electric flame-effect stove. Character features. Washing machine. Barnard Castle 8.9 miles; Leyburn 14.3 miles. (Ref. 1107452)

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


for 7 nights From £747

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £364

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £463

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From £345

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £423

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From £321