Winston Holiday Cottages

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Winston Holiday Cottages

Your Winston, Durham search returned 113 cottages

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How reviews work

A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A stone cottage with a white door and two windows with plants and flowers outside at Curlew Cottage in Barnard Castle
6
Barnard Castle, County Durham, DL12
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

This elegantly furnished all ground floor cottage provides cosy accommodation in a lovely countryside location. With a multi-fuel stove, front patio and BBQ. Bike storage. Barnard Castle 2 miles. (Ref. 21863)

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


for 7 nights $428

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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
46
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


for 7 nights $494

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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


for 7 nights $707

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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


for 7 nights $628

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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
Offer
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

  • 15% off - Mon 20th Apr to 30th Jun 2026


for 7 nights $634

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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

    4.8★

    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


for 7 nights $496

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Stone cottage exterior with a wooden door and potted plants at Rose Cottage in Winston
26
Winston, County Durham, DL2
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

This delightful, terraced, stone cottage is located in Winston, Durham. WiFi. Electric fire. Barnard Castle 6 miles; Darlington 10 miles. (Ref. 998937)

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


for 7 nights $481

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Stone house exterior with four white framed windows two topiary plants by a dark door at Deanery View in Staindrop Nr Barnard Castle
37
Staindrop, Nr Barnard Castle, County Durham, DL2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A spectacular three-bedroom holiday home settled in the quaint village of Staindrop in County Durham. Patio garden. En-suite. Washer/dryer. Barnard Castle 5.5 miles; Durham 19 miles. (Ref. 1082990)

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


for 7 nights $803

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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

    5.0★

    Perfect

  • 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


for 7 nights $440

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A small wooden cabin with a hot tub picnic table broom and net outside at Badgers Sett Winston near Staindrop
Offer
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

  • 15% off - Mon 20th Apr to 30th Jun 2026


for 7 nights $682

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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


for 7 nights $418

Last booked 2 days ago
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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

  • 15% off - Mon 20th Apr to 30th Jun 2026


for 7 nights $634

Last booked yesterday
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A black door with the number 1 and a plaque that reads The Printshop on a stone wall at The Print Shop in Barnard Castle
28
Barnard Castle, County Durham, DL12
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A lovely, one-bedroom cottage resting in Barnard Castle, County Durham. Close to amenities. Romantic. Pet-free. Staindrop 5.9 miles; Richmond 14.8 miles; Darlington 15.7 miles; Durham 24.5 miles. (Ref. 1103483)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights $400

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A river with bushes and trees along the bank and houses on a stone wall in Barnard Castle
56
Barnard Castle, County Durham, DL12
  • 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


for 7 nights $644

Last booked yesterday
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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


for 7 nights $558

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A small wooden cabin with a porch in a wooded area with bare trees at Bracken Fern in Eppleby
36
Eppleby, North Yorkshire, DL11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This charming shepherd’s hut resides in Richmond, North Yorkshire. Wood-fired hot tub. Woodland setting. Rural. Richmond 8.8 miles; Barnard Castle 11.8 miles; Leyburn 17.7 miles. (Ref. 1022245)

  • Off-road parking
  • Ground floor bedroom
  • Hot Tub


for 7 nights $556

Last booked yesterday
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A wooden cabin with a covered porch and a fire pit in front surrounded by trees at The Leveret in Eppleby
19
Eppleby, North Yorkshire, DL11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

The Leveret is a stunning, rustic camping pod just outside of the lovely village of Eppleby in Richmondshire. Countryside. Hot tub. Woodburning stove. Richmond 9.8 miles. (Ref. 1136837)

  • Off-road parking
  • Ground floor bedroom
  • Hot Tub


for 7 nights $594

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The exterior of a stone cottage with three windows a door and multiple potted plants outside the entrance at Fern Cottage in Butterknowle
18
Butterknowle, County Durham, DL13
  • 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 $424

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A stone courtyard with tiled roof buildings and a garden bed with flowers and plants at The Dairy in Ramshaw near Evenwood
47
Ramshaw near Evenwood, County Durham, DL14
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • 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


for 7 nights $674

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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


for 7 nights $1348

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Map View

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