Winston Holiday Cottages

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Your Winston, Durham search returned 115 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

The Leveret is a stunning, rustic camping pod just outside of the lovely village of Eppleby in Richmondshire. Countryside. Hot tub. Woodburning stove. Richmond 9.8 miles. (Ref. 1136837)

  • Off-road parking
  • Ground floor bedroom
  • Hot Tub

7 nights from £447

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9

    Good

  • Sykes rating

Cosy romantic retreat set amongst rolling countryside in a quiet corner of Teesdale. Ground floor studio accommodation with king-size double bed. WiFi. Barnard Castle 8 miles. (Ref. 927831)

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

7 nights from £301

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A contemporary, single-storey cottage resting in the village of Copley, near Barnard Castle, in County Durham. Ground-floor living. Romantic. Patio. WiFi. Staindrop 6.1 miles; Darlington 16.4 miles; Durham 20.5 miles; Richmond 21.2 miles. (Ref. 1077164)

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

7 nights from £276

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Foxes Den, a wonderful, single-storey lodge resting in Winston near Staindrop. Hot tub. Pet-friendly. Private parking. Barnard Castle 7.2 miles; Durham 20.2 miles. (Ref. 1082438)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • 5% off - Fri 20th Jun to 5th Sep 2025

7 nights from £591

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9

    Good

  • Sykes rating

Hawthorn Cottage is an end-of-terrace barn conversion situated in a rural complex on the outskirts of of Caldwell, Durham. Romantic. Pet-friendly. Enclosed courtyard. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142453)

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

7 nights from £325

  • 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

7 nights from £354

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.0

    Good

  • Sykes rating

End-terrace cottage with wood-fired hot tub and woodburning stove. Pet-friendly. WiFi. Spacious accommodation. Barnard Castle 8 miles. (Ref. 927830)

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

7 nights from £530

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An exceptional stable conversion resting on the outskirts of Barnard Castle in North Yorkshire. Single-storey accommodation. Open-plan living. WiFi. Hot tub. Middleton in Teesdale 12.8 miles; Richmond 15 miles. (Ref. 1078952)

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

7 nights from £1273

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Fantastic, detached townhouse in the market town of Barnard Castle. Ideal for family and friends with flexible accommodation. WiFi, off road parking. Caldwell 9 miles. (Ref. 929734)

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

7 nights from £557

  • Sleeps5
  • Bedrooms3
  • PetsNo
  • Sykes rating

Artist’s Cottage is a delightful cottage in Richmond, North Yorkshire, well-positioned to an array of attractions and boasting a woodburning stove. Leyburn 9 miles; Darlington 13 miles; Barnard Castle 15.1 miles; Middlesborough 28.7. (Ref. 1163443)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £488

  • 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

7 nights from £486

  • 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

    4.5

    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)

  • Wi-fi
  • Washing machine

7 nights from £403

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This delightful annexe rests on the outskirts of Eggleston, near Middleton-in-Teesdale, County Durham. Woodburning stove. Pet-friendly. En-suite. Barnard Castle 5.1 miles; North Pennines AONB 13.6 miles. (Ref. 1036975)

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

7 nights from £391

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

This attractive, mid-terrace cottage sits in the heart of Richmond, Yorkshire. Open-plan. Woodburning stove. Cinema room. Catterick 5.4 miles; Leyburn 9.1 miles; Barnard Castle 14.3 miles. (Ref. 1038663)

  • Wi-fi

7 nights from £398

  • 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

    4.9

    Outstanding

  • Sykes rating

A homely Grade II listed cottage in the centre of Richmond market town in North Yorkshire. Courtyard. Pet friendly. WiFi. Colburn 3.2 miles; Leyburn 8.5 miles; Darlington 12.6 miles. (Ref. 1054760)

  • Wi-fi
  • Washing machine

7 nights from £424

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from £399

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

    4.8

    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