Winston Holiday Cottages

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British Travel Award Winners!

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 €380

Last booked yesterday
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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 €619

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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 €483

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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


for 7 nights €550

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A stone house with solar panels on the roof behind a stone wall and a tree at Forestside View in Woodland
69
Woodland, County Durham, DL13
  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Forestside View is a fabulous, four-bedroom home enjoying countryside views in Woodland, Durham. Rural. Contemporary. Near National Park. Pet-friendly. Barnard Castle 7.8 miles; Bishop Auckland 10.8 miles; Darlington 18.2 miles. (Ref. 1139295)

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


for 7 nights €922

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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 €534

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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 €1085

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A stone cottage exterior with maroon framed windows and door and potted plants outside at Grove Cottage in Butterknowle
13
Butterknowle, County Durham, DL13
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Semi-detached, luxury barn conversion. Beams and trusses and multi-fuel stove. Well-equipped and comfortable. Good base for Northern Dales and County Durham. Barnard Castle 10 miles. (Ref. 920252)

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


for 7 nights €366

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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 €527

Last booked yesterday
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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 €511

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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 €418

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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 €583

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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

    5.0★

    Perfect

  • 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


for 7 nights €1963

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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 €550

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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 €569

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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 €490

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The exterior of a stone house with a gray door and windows at 45 South Green in Staindrop
34
Staindrop, County Durham, DL2
  • Sleeps6
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A traditional, end-of-terrace cottage located in the village of Staindrop, within the county of Durham. Pet-friendly. Woodburning stove. Ideal for families. Barnard Castle 5.6 miles; Durham 18.9 miles. (Ref. 1084931)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €441

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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 €332

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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 €441

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


for 7 nights €688

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Map View

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