Winston Holiday Cottages

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We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Winston Holiday Cottages

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Your Winston, Durham search returned 113 cottages

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Map View
A stone house with white framed windows and doors with a patio area featuring a dining table and six chairs at Hall Cottage in Ovington
33
Ovington, County Durham, DL11
  • 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 £533

Last booked yesterday
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Stone cottage with two white-framed windows and green wooden doors at Garden Cottage in Ovington
11
Ovington, County Durham, DL11
  • 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 £369

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A row of shops on a street including a bespoke tailoring shop and a gelato store at The Flat in Barnard Castle
32
Barnard Castle, County Durham, DL12
  • 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 £343

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A stone house with a blue door and garden chairs on a lawn at Mill Farm House in Ravensworth
49
Ravensworth, North Yorkshire, DL11
  • 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 £1702

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A stone house with a tiled roof and glass porch surrounded by a garden with trimmed hedges and a birdbath at The Sycamores in Forcett near Eppleby
49
Forcett near Eppleby, North Yorkshire, DL11
  • 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 £889

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A small wooden cabin with a porch and hot tub outside at Otters Holt in Winston near Staindrop
Offer
55
Winston near Staindrop, County Durham, DL2
  • 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 £478

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A garden with pink flowers in front of a stone house with a wooden balcony at Folly Lodge in Eggleston near Middleton-In-Teesdale
40
Eggleston near Middleton-In-Teesdale, County Durham, DL12
  • 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 £391

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A small wooden cabin with a hot tub picnic table broom and net outside at Badgers Sett Winston near Staindrop
57
Winston near Staindrop, County Durham, DL2
  • 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

7 nights from £474

Last booked yesterday
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Stone exterior of a two door house with two windows and greenery behind the low stone wall at Magnolia Cottage in Barton
22
Barton, North Yorkshire, DL10
  • 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 £453

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A wooden deck with two chairs and a railing overlooking a gravel pathway leading to a wooden hot tub and grassy area at Foxes Den in Winston near Staindrop
50
Winston near Staindrop, County Durham, DL2
  • 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

7 nights from £474

Last booked yesterday
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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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Stone cottage with a white door and three windows on a paved street at Stable Cottage in Boldron near Barnard Castle
46
Boldron near Barnard Castle, County Durham, DL12
  • 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 £563

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A white cottage with a red tiled roof a white door and lattice windows with a garden path and stone planters at Appletree Cottage in Richmond
44
Richmond, County Durham, DL11
  • 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 £367

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A stone cottage with red tiled roof green door and surrounding trees at Alwent Mill Winston near Staindrop
46
Winston near Staindrop, County Durham, DL2
  • 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

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Stone cottage exterior with green door and bay window surrounded by plants and flowers at Wayside Cottage in Staindrop
24
Staindrop, County Durham, DL2
  • 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 £284

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A patio with a glass table and two chairs next to a brick building with a dark door and large windows at Leadmill Piggery in Copley near Barnard Castle
26
Copley near Barnard Castle, County Durham, DL13
  • 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

Last booked yesterday
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White two-story house with blue door white door with wreath bay window and potted plants on the front patio at Dale Cottage in Ingleton County Durham
51
Ingleton, County Durham, Yorkshire Dales - North, DL2
  • 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 £462

Last booked 2 days ago
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A stone building with a gravel driveway and grassy area with trees at The Byre Sedbury Park Farm in Gilling West
46
Gilling West, North Yorkshire, DL10
  • 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 £640

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Stone building with red tile roof and green painted doors and windows with two potted plants and a bicycle outside at The Cartshed Sedbury Park Farm in Gilling West near Richmond
42
Gilling West near Richmond, North Yorkshire, DL10
  • 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 £527

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A stone row house with white and black front doors and iron gate surrounded by green hedges at Stang View in Barnard Castle
45
Barnard Castle, County Durham, DL12
  • 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 £418

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Map View

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