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 109 cottages

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Map View
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 £327

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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 £533

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


for 7 nights £416

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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


for 7 nights £369

Last booked yesterday
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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


for 7 nights £438

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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, Yorkshire Dales - North, 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


for 7 nights £474

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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

    4.9★

    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


for 7 nights £502

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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

    5.0★

    Perfect

  • 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 £491

Last booked yesterday
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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 £940

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A small wooden cabin with a porch and hot tub outside at Otters Holt in Winston near Staindrop
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


for 7 nights £478

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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


for 7 nights £474

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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

    4.8★

    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


for 7 nights £581

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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 £454

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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


for 7 nights £376

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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


for 7 nights £253

Last booked yesterday
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A small wooden cabin with a porch in a wooded area with bare trees at Bracken Fern in Eppleby
39
Eppleby, North Yorkshire, DL11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • 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 £447

Last booked yesterday
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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

    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


for 7 nights £490

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A stone house with large windows a flower bed and outdoor seating at Jacob's Lodge in Eggleston
95
Eggleston, County Durham, DL12
  • 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 £2151

Last booked yesterday
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A stone exterior wall with three windows two doors a lantern and a plant in a pot at The Netty in Richmond
22
Richmond, North Yorkshire, DL11
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A lovely single-storey cottage next to the owner's home in East Layton, near Eppleby, North Yorkshire. Woodburning stove. Open-plan. Romantic. Off-road parking. Patio. Richmond 7.5 miles; (Ref. 1072404)

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


for 7 nights £422

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The entrance of a stone house with a blue door a window and an outdoor table and chairs at The Carriage House in Barnard Castle
35
Barnard Castle, County Durham, DL12
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Fantastic, detached townhouse in the market town of Barnard Castle. Ideal for family and friends with flexible accommodation. WiFi, off road parking. Caldwell 9 miles. (Ref. 929734)

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


for 7 nights £621

Last booked yesterday
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Map View

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