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

Immaculate, detached property in a quiet street near the centre of Darlington. Contemporary, spacious accommodation. Close to restaurants, pubs and railway attractions. Short drive to market towns of Richmond and Barnard Castle. Good touring base. (Ref. 920812)

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

7 nights from £441

  • 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

7 nights from £350

  • 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

7 nights from £330

  • 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 £454

  • 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 £318

  • 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 £661

  • 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 £987

  • 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 £933

  • 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 £1198

  • 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
  • £136 off - Fri 4th Jul to 11th Jul 2025

  • £363 off - Fri 18th Jul to 25th Jul 2025

7 nights from £803

  • 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 £1165

  • 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 £374

  • 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

    4.8

    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 £311

  • 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

    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 £608

  • 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 £594

  • 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

  • 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 £276

Last booked 2 days ago
See more details
  • 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