Winston Holiday Cottages

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Your Winston, Durham search returned 106 cottages

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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

The Farm House, a charming holiday cottage resting by Aldbrough St. John, Yorkshire. Hot tub. Smart TV. Woodburning stove. Pet-friendly. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1179009)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £1666

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.3

    Good

  • Sykes rating

An inviting, single-storey cottage set amidst rolling countryside in County Durham, just outside the small village of Ingleton. Woodburning stove. Ideally positioned for touring North Pennines. Barnard Castle 7.8 miles. (Ref. 1039115)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £429

  • Sleeps16
  • Bedrooms7
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Outstanding property surrounded by impressive countryside views. External leisure suite with hot tub and sauna. Ground floor bedrooms, en-suites. Two sitting rooms, one with woodburner. Barnard Castle 6 miles. (Ref. 927149)

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


for 7 nights £2093

  • 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


for 7 nights £352

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    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


for 7 nights £392

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A delightful stone-built, semi-detached cottage just two minutes from the centre of Richmond. King-size bed, off road parking, enclosed garden. Ideal for a couple. Barnard Castle 10 miles. (Ref. 955196)

  • Wi-fi
  • Off-road parking


for 7 nights £348

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    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


for 7 nights £938

  • 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


for 7 nights £354

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • 15% off - Fri 9th Jan to 13th Jan 2026

  • 15% off - Fri 16th Jan to 20th Jan 2026

  • 15% off - Fri 23rd Jan to 27th Jan 2026

  • 15% off - Fri 30th Jan to 3rd Feb 2026

  • 15% off - Fri 6th Feb to 10th Feb 2026


for 7 nights £696

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £444

  • 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


for 7 nights £1001

  • 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


for 7 nights £397

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £562

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • 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. 1179013)

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


for 7 nights £1132

  • 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


for 7 nights £554

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.8

    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)

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


for 7 nights £809

  • 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


for 7 nights £354

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A luxury cottage in the village of Butterknowle. Modern bathroom. Open plan. Multi-fuel stove. WiFi. Close to Hamsterley Forest and surrounding area. Barnard Castle 10 miles. (Ref. 920251)

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


for 7 nights £328

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    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)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights £404

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Good

  • Sykes rating

Bowes Hideaway, a charming studio-style lodge perched on the Hillcrest Holiday Park in Caldwell, Durham, boasting a hot tub and ample off-road parking. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142457)

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


for 7 nights £561