Winston Holiday Cottages

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Your Winston, Durham search returned 116 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From €437

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.8

    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)

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


for 7 nights From €1123

  • Sleeps4
  • Bedrooms1
  • Pet FriendlyYes

    4.7

    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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights From €342

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Character, semi-detached Grade II listed cottage in Barnard Castle. Ideal for families and friends alike. WiFi, pet-friendly. Great base for exploring the Yorkshire Dales. Caldwell 9 miles. (Ref. 931727)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €444

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A Grade II listed terraced cottage in the village of Melsonby. Large enclosed garden. Woodburning stove. Character features. Richmond 5.7 miles; Darlington 8.3 miles; Barnard Castle 12.8 miles. (Ref. 1020656)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From €712

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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


for 7 nights From €312

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From €334

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A traditional stone cottage in the village of Cotherstone, Durham. Original features. Romantic dwelling. Pet-friendly. Last-minute and weekend breaks. Outstanding surroundings. Barnard Castle 4.2 miles; Newbiggin 9.2 miles; Bishop Auckland 18.9 miles. (Ref. 1058422)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From €592

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly


for 7 nights From €296

Last booked yesterday
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  • Sleeps16
  • Bedrooms7
  • Pet FriendlyNo

    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 From €2485

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

A delightful stone-built, semi-detached cottage just two minutes from the centre of Richmond. King-size bed, off road parking, enclosed garden. Ideal for a couple. Barnard Castle 10 miles. (Ref. 1197330)

  • Wi-fi
  • Off-road parking


for 7 nights From €415

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Churchill Cottage, a welcoming abode resting in Bishop Auckland, County Durham, offers private parking, an enclosed garden and pet-friendly accommodation. Durham 10.5 miles. (Ref. 1199564)

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


for 7 nights From €559

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Baytree Cottage rests in Richmond, North Yorkshire, Multiple Winner of the Perfect 10 Rating Award. Free parking. Pet-friendly. Yorkshire Dales National Park 11.1 miles; Darlington 13.4 miles. (Ref. 1139017)

  • Pets go free
  • Wi-fi
  • Washing machine
  • Sky TV
  • 5% off - Tue 27th Oct to 7th Nov 2026


for 7 nights From €755

  • Sleeps5
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

27 West Green is a delightful terraced cottage resting in the village of Heighington, Durham, with a garden and woodburning stove. Bishop Auckland 5.9 miles; Darlington 6.3 miles; Durham 15.1 miles. (Ref. 1196010)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €927

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.3

    Good

  • Sykes rating

An inviting, single-storey cottage set amidst rolling countryside in County Durham, just outside the small village of Ingleton. Woodburning stove. Ideally positioned for touring North Pennines. Barnard Castle 7.8 miles. (Ref. 1039115)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From €497

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €529

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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


for 7 nights From €503

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A stone-built terraced cottage resting on the outskirts of Richmond. Pet-friendly. Off-road parking. Barnard Castle 15.5 miles. (Ref. 1053055)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Washing machine


for 7 nights From €478

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €505

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Bishop Lightfoot Cottage, a charming pet-friendly cottage in Bishop Auckland, Durham, with private parking, an enclosed garden and proximity to amenities. Durham 10.5 miles. (Ref. 1201082)

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


for 7 nights From €616