Winston Holiday Cottages

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Your Winston, Durham search returned 115 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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

7 nights from £341

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Superb barn conversion in small courtyard setting between Barnard Castle and Middleton. Character beams, woodburning stove, en-suites to both bedrooms. Glorious views, ideal walking country. Barnard Castle 4 miles. (Ref. 16399)

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

7 nights from £446

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.8

    Good

  • Sykes rating

Willow Cottage is a delightful, two-bedroom abode resting in Caldwell near Eppleby, Durham. Pet-friendly. Enclosed garden. Near National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142455)

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

7 nights from £366

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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

7 nights from £438

Last booked yesterday
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  • 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

7 nights from £537

Last booked 2 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Maple Cottage is a wonderful property in Ingleton, Teesdale, County Durham, boasting a woodburning stove in the living area alongside bedroom countryside views. Barnard Castle 8.9 miles; Durham 18.4 miles. (Ref. 1174055)

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

7 nights from £427

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • 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)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £428

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • 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)

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

7 nights from £435

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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

7 nights from £400

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Character, semi-detached Grade II listed cottage in Barnard Castle. Ideal for families and friends alike. WiFi, pet-friendly. Great base for exploring the Yorkshire Dales. Caldwell 9 miles. (Ref. 931727)

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

7 nights from £376

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A well-positioned two-bedroom cottage resting in Ingleton near Gainford, Durham. Hot tub. Countryside views. Woodburning stove. Pet-friendly. Open-plan. Raby Castle 4.1 miles; Barnard Castle 8.8 miles; Darlington 8.5 miles. (Ref. 1101654)

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

7 nights from £469

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.5

    Good

  • Sykes rating

Elder Cottage is a delightful cottage resting on the Hillcrest Holiday Park in Caldwell, Durham. Romantic. Freestanding bath. Near a National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1147942)

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

7 nights from £334

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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

7 nights from £402

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A beautiful period terrace resting in the ancient town of Barnard Castle, County Durham. Woodburning stove. Enclosed garden. Central location. Staindrop 6.3 miles; Richmond 14.7 miles; Darlington 16.2 miles. (Ref. 1027047)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £418

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £465

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from £522

  • 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

7 nights from £398

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2

    Good

  • Sykes rating

Ivy Cottage is a delightful cottage resting on the Hillcrest Holiday Park in Caldwell, Durham. Romantic. Freestanding bath. Near a National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1147943)

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

7 nights from £334

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Baytree Cottage rests in Richmond, North Yorkshire, Multiple Winner of the Perfect 10 Rating Award. Free parking. Pet-friendly. Yorkshire Dales National Park 11.1 miles; Darlington 13.4 miles. (Ref. 1139017)

  • Wi-fi
  • Washing machine
  • Sky TV
  • 15% off - Fri 18th Jul to 26th Jul 2025

  • 17% off - Fri 25th Jul to 29th Aug 2025

  • 15% off - Sat 26th Jul to 2nd Aug 2025

  • 5% off - Sat 2nd Aug to 9th Aug 2025

  • 10% off - Sat 9th Aug to 16th Aug 2025

  • 5% off - Sat 16th Aug to 23rd Aug 2025

7 nights from £563