Winston Holiday Cottages

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Your Winston, Durham search returned 115 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Beautiful cottage for four with two en-suite bedrooms, multi-fuel stove, off street parking and secure bike storage. At the gateway to The Yorkshire Dales this cottage is a perfectly cosy retreat. (Ref. 949020)

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

7 nights from €538

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful single-storey cottage in the village of Winston, two miles from Staindrop. Tastefully furnished with beautiful grounds. Close to many attractions. Barnard Castle 7 miles. (Ref. 917587)

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

7 nights from €539

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

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Superb two bedroom cottage with a multi-fuel stove and panoramic countryside views. Bike storage, patio with furniture and BBQ. Barnard Castle 2 miles. (Ref. 21862)

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

7 nights from €377

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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

7 nights from €749

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A first class 18th century apartment located in the centre of Barnard Castle. Stylish throughout with a blend of modern and original features. WiFi. Off road parking. Perfect location for a romantic break. (Ref. 918609)

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

7 nights from €407

  • 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

7 nights from €1109

  • 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

7 nights from €1173

  • Sleeps8
  • Bedrooms4
  • PetsYes

    3.8

    Good

  • Sykes rating

A fantastic, terraced cottage perched in the heart of Barnard Castle, County Durham. Dog-friendly. Pool table. Close to amenities. Near a National Park. Off-road parking. Staindrop 5.8 miles; Richmond 14.8 miles; Darlington 15.7 miles. (Ref. 1062818)

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

7 nights from €785

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Forestside View is a fabulous, four-bedroom home enjoying countryside views in Woodland, Durham. Rural. Contemporary. Near National Park. Pet-friendly. Barnard Castle 7.8 miles; Bishop Auckland 10.8 miles; Darlington 18.2 miles. (Ref. 1139295)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • €162 off - Fri 4th Jul to 11th Jul 2025

  • €432 off - Fri 18th Jul to 25th Jul 2025

7 nights from €944

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

The Gate House, a delightful holiday cottage in Aldbrough St. John, Yorkshire. Smart TV. Woodburning stove. Pet-friendly. Hot tub. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1144502)

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

7 nights from €1424

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Hollymoor Hall Farm is a lovely, pet-friendly detached holiday home resting in the lovely town of Richmond in North Yorkshire with a woodburning stove. Leyburn 9.5 miles; Barnard Castle 14.7 miles. (Ref. 1171138)

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

7 nights from €1385

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming stone-built cottage in the hamlet of Ovington. Romantic accommodation with a woodburning stove. Pet-friendly property with enclosed garden. Ideal touring base. Barnard Castle 8 miles. (Ref. 1021694)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Sky TV

7 nights from €444

  • 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

7 nights from €327

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This delightful Grade II listed end-terrace cottage rests in Staindrop, Durham. Close to amenities. Pet-friendly. Courtyard with furniture. WiFi. Barnard Castle 5.6 miles; Durham 18.9 miles. (Ref. 1067929)

  • Wi-fi
  • Washing machine

7 nights from €369

  • 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 €327

  • 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 €357

  • 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 €420

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Otters Holt, a fabulous, single-story lodge located in Winston near Staindrop, County Durham. Open-plan. Hot tub. Smart TV. Beautiful views. Pet friendly. Private parking. Barnard Castle 7.2 miles; Durham 20.2 miles. (Ref. 1082439)

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

7 nights from €694

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A stone cottage situated in the village of Barnard Castle, Durham. Shared patio. Quirky interior. One pet welcome. Staindrop 6 miles; Richmond 13 miles. (Ref. 983102)

  • Wi-fi
  • Dishwasher

7 nights from €369

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Badgers Sett, a superb single-storey lodge resting in Winston near Staindrop, Durham. Pet-friendly. Hot tub. Private parking. Barnard Castle 7.2 miles; Durham 20.2 miles. (Ref. 1027477)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • 5% off - Fri 20th Jun to 25th Jul 2025

7 nights from €711