Winston Holiday Cottages

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Your Winston, Durham search returned 108 cottages

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A stone house with a dark roof and two arched windows a tree in front and a stone pathway on a grassy lawn at Woodland View in Richmond
28
Richmond, North Yorkshire, DL10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A contemporary first-floor apartment resting on the outskirts of Richmond in North Yorkshire. Open-plan. Private hot tub. Romantic. Darlington 14.6 miles; Northallerton 17.3 miles. (Ref. 1070889)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from £603

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An open plan living and dining area with a dining table and chairs a sofa and armchair a wood stove and a TV near large glass doors leading to a garden at The Barn in Copley
37
Copley, County Durham, DL13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Barn is a delightful, single-storey holiday cottage situated in Copley near Cockfield, Durham. Woodburning stove. Smart TV. Off-road parking. Bishop Auckland 10 miles; Durham 19.1 miles. (Ref. 1150077)

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

7 nights from £271

Last booked yesterday
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Stone house exterior with white door and windows a green mailbox and small wooden gate at Falcus Cottage in Stainton near Barnard Castle
53
Stainton near Barnard Castle, County Durham, DL12
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming three-bedroom terraced cottage resting in Stainton, Durham. Pet-friendly. Enclosed garden. Woodburning stove. Close to amenities. Staindrop 4.2 miles; Richmond 17.2 miles; Darlington 15.7 miles. (Ref. 1063315)

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

7 nights from £445

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A stone house exterior with wooden bench potted plants and windows at The Cote in Staindrop near Barnard Castle
53
Staindrop near Barnard Castle, County Durham, DL2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Traditional stone cottage near Staindrop. Beautiful rural location. Underfloor heating. Panoramic views. Comfortable family accommodation. Ideal walking, touring. Barnard Castle 5 miles. (Ref. 16414)

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

7 nights from £442

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A row of stone and plaster houses with white and light green doors on a street at Ivy Cottage in Richmond
37
Richmond, North Yorkshire, DL10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Ivy Cottage is a delightful, pet-friendly house resting near an array of attractions in Richmond, Yorkshire, boasting an enclosed garden and Smart TV. Leyburn 9.3 miles; Barnard Castle 14.6 miles; Middlesborough 28.2 miles; Hartlepool 36.6 miles. (Ref. 1166505)

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

7 nights from £438

Last booked yesterday
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A stone barn building with a wooden gate and gravel path at The Tithe Barn in Brignall near Barnard Castle
46
Brignall near Barnard Castle, County Durham, DL12
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

The Tithe Barn is a superb, detached Grade II listed property resting in Brignall, Durham. Woodburning stove. Off-road parking. Enclosed garden. Pet-friendly. Staindrop 10.2 miles; Richmond 12.6 miles; Darlington 19.4 miles. (Ref. 1094080)

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

7 nights from £936

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A living room with a stone fireplace and wood stove a blue armchair and sofa with pink cushions and a grandfather clock at 3 Mill Wynd in Staindrop
37
Staindrop, County Durham, DL2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A two-bedroom, stone-fronted cottage resting in Staindrop, Durham. Close to amenities. Woodburning stove. Pet-friendly. Raby Castle 1.7 miles; Barnard Castle 5.5 miles; Durham 19 miles. (Ref. 1097522)

  • Wi-fi

7 nights from £380

Last booked 8 hours ago
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A stone house with a tiled roof surrounded by a low stone wall and a lawn with trees at Wellberry in Hilton near Staindrop
21
Hilton near Staindrop, County Durham, DL2
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A charming single-storey cottage on a working farm, 2.3 miles from the village of Staindrop in Teeside. Spacious accommodation suitable for all family members. WiFi. Excellent walking from the doorstep. Great touring base. Barnard Castle 8 miles. (Ref. 30509)

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

7 nights from £386

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A stone house exterior with blue door white window frames and potted plants at The Back House in Staindrop
46
Staindrop, County Durham, DL2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming stone cottage tucked away in the village of Staindrop in County Durham. Pet-friendly. Woodburning stove. Smart TV. Close to amenities. Gainford 4.5 miles; Barnard Castle 5.8 miles. Please contact us if you wish to book between 23 and 28 April o (Ref. 981909)

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

7 nights from £725

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A stone building with wooden doors and windows a gravel courtyard and outdoor table with chairs at Padley Barn in Hurst near Reeth
43
Hurst near Reeth, North Yorkshire, DL11
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A superb stone barn conversion in a rural location, 0.5 miles from the hamlet of Hurst. Flagged floors, woodburning stove, contemporary kitchen and bathrooms. Very comfortable and well equipped. Walking and cycling from doorstep. Reeth 5 miles. (Ref. 20841)

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

7 nights from £479

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A stone building with wooden framed windows solar panels on the roof and a brick wall in front at Leadmill House Workshop in Copley near Barnard Castle
30
Copley near Barnard Castle, County Durham, DL13
  • 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 £253

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A castle-like stone building with a wooden fence and gravel driveway at Walworth Castle Lodge in Walworth near Darlington
40
Walworth near Darlington, North East England, DL2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Walworth Castle Lodge is a beautifully presented, pet-friendly, stone-built cottage nestled in the small village of Walworth near Darlington, Durham. Yarm 16.6 miles; Richmond 14.8 miles. (Ref. 1165778)

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

7 nights from £847

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Stone exterior of a house with gray door and multiple windows with blinds at The Little Flat in Barnard Castle
13
Barnard Castle, County Durham, DL12
  • 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 £290

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An outdoor courtyard with stone and brick buildings a green artificial hedge a concrete floor and hanging flower baskets at Ferngrove Cottage in Butterknowle
22
Butterknowle, County Durham, DL13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A charming barn conversion nestled in the rural village of Butterknowle, County Durham. Open-plan living. Shared courtyard. Bishop Auckland 8.2 miles. (Ref. 996441)

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

7 nights from £279

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A small outdoor patio with a metal table and chairs in front of a two-story house at Magnolia Cottage in Melsonby
28
Melsonby, North Yorkshire, DL10
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A well-presented stone terrace cottage resting in the sleepy village of Melsonby. Multi-fuel stove. Smart TV. WiFi. Dog-friendly. Modern finish. Yorkshire Dales. (Ref. 974062)

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

7 nights from £388

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A stone cottage with skylights and wooden door behind garden with flowers and wooden table and chairs at Dale View Woodland near Cockfield
26
Woodland near Cockfield, County Durham, DL13
  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Dale View is a single-storey couple’s retreat resting in Woodland near Cockfield, Durham. Woodburning stove. Pet-friendly. Garden. Cockfield 4.6 miles; Barnard Castle 7.3 miles; Bishop Aukland 10.6 miles. (Ref. 1139851)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £294

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A white building with a blue door and windows at Peace Cottage in Langton near Gainford
38
Langton, County Durham, DL2
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Peace Cottage is a beautiful, pet-friendly cottage near Langton in Durham, boasting a woodburning stove, off-road parking, and stunning countryside views. Darlington 9.3 miles; Barnard Castle 9.7 miles; Richmond 15.4 miles; Durham 19.4 miles. (Ref. 1170306)

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

  • £20 off - Mon 27th Oct 2025 to 2nd Jan 2026

7 nights from £586

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A house with a gate and trees in a garden at The Gate House in Aldbrough St. John near Barton
60
Aldbrough St. John near Barton, North Yorkshire, DL11
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5★

    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. 1179012)

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

7 nights from £1159

Last booked yesterday
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A stone exterior wall with three green doors two windows a bench and potted plants at Low Shipley Cottage in Barnard Castle
30
Barnard Castle, County Durham, DL12
  • 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 £452

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The exterior of a stone cottage with a red tiled roof a white door and windows surrounded by greenery and a bench in a garden at Corner Cottage Staindrop near Barnard Castle
35
Staindrop near Barnard Castle, County Durham, DL2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A charming cottage in the pretty Durham village of Staindrop. Pet-friendly with woodburning stove. Perfect for touring The Durham Dales. Barnard Castle 5 miles. (Ref. 943949)

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

7 nights from £436

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