Winston Holiday Cottages

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Your Winston, Durham search returned 115 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A stone-built, terraced cottage in the peaceful hamlet of Ovington, County Durham. Lovely views. 5 x TVs with Freeview. 3 pets welcome. Barbecue. Barnard Castle 6.6 miles; Richmond 12.3 miles. (Ref. 1045366)

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

7 nights from $721

  • 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 $464

  • 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 $506

  • 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 $790

  • Sleeps16
  • Bedrooms8
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Charming stone-built, grade II listed farmhouse nestled in the quaint village of Ravensworth, North Yorkshire. WiFi. Dog friendly. Richmond 4.5 miles. (Ref. 988514)

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

7 nights from $2287

  • 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 $566

Last booked yesterday
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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 $613

  • 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 $374

  • 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 $578

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A lovely, two-bedroom home resting in Ovington near Gainford, Durham. Pet-friendly. Close to amenities and river. Near National Park. Woodburning stove. Barnard Castle 7.7 miles; Richmond 11.5 miles; Darlington 12.1 miles. (Ref. 1117841)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from $512

  • 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 $809

  • 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 $614

  • 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 $529

  • 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 $634

  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

The Dairy, a lovely holiday cottage resting in the peaceful village of Ramshaw, Durham. Underfloor heating. Pet-friendly. Woodburning stove. En-suite. Darlington 14.1 miles; Durham 15.5 miles (Ref. 1151044)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from $663

  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Superb barn conversion in Gilling West. WiFi, en-suite, woodburner, garden. Spacous welcoming accommodation with beams, finished to a high standard. Pub 15 mins walk. (Ref. 934810)

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

7 nights from $713

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

18 Thorngate Wynd is a wonderful, dog-friendly holiday cottage in Barnard Castle, County Durham with breathtaking views over the River Tees. Staindrop 6.3 miles; Richmond 15.1 miles; Darlington 16.3 miles; Durham 24.9 miles. (Ref. 1149426)

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

7 nights from $595

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming semi-detached cottage resting in the quaint village of Boldron near Barnard Castle. Large lawn garden. Hot tub. Pet friendly. Barnard Castle 2.5 miles; Staindrop 8.3 miles; Richmond 15.4 miles. (Ref. 1067566)

  • Wi-fi
  • Electric vehicle charging
  • Hot Tub
  • Washing machine
  • Baby-friendly

7 nights from $869

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A traditional stone-fronted cottage, resting in the delightful village of Forcett, Richmond. Woodburning stove. Scenic location. WiFi. Richmond 8.5 miles. Middlesbrough 25.1 miles. (Ref. 1003360)

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

7 nights from $1253

  • 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

7 nights from $2907

Please find below a selection of self catering holiday cottages to rent in or near Winston.