24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Winston Holiday Cottages

REFINE SEARCH

Your Winston, Durham search returned 132 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.6

    Good

  • Sykes rating

Hawthorn Cottage is an end-of-terrace barn conversion situated in a rural complex on the outskirts of of Caldwell, Durham. Romantic. Pet-friendly. Enclosed courtyard. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142453)

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

7 nights from £317

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £371

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Quality barn conversion near Gilling West. En-suite, welcoming accommodation with WiFi, garden. Close to walks, village pub, ideal touring base. (Ref. 934811)

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

7 nights from £382

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

The Gate House, a delightful holiday cottage in Aldbrough St. John, Yorkshire. Smart TV. Woodburning stove. Pet-friendly. Hot tub. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1144502)

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

7 nights from £1176

Last booked 3 hours ago
See more details
  • 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

7 nights from £482

Last booked 2 hours ago
See more details
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

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 £592

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Good

  • Sykes rating

A well-located first-floor apartment resting in the heart of Richmond, North Yorkshire. Designated parking. Close to amenities. Pet free. Open-plan. Leyburn 9 miles; Barnard Castle 15 miles. (Ref. 1102415)

  • Wi-fi

7 nights from £368

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

An attractive cottage situated in the village of Walworth, Durham. Ground-floor living. Woodburning stove. Outstanding views. Darlington 5.6 miles. Spennymoor 12.7 miles. Barnard Castle 13.6 miles. (Ref. 1034430)

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

7 nights from £744

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

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

7 nights from £592

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9

    Good

  • Sykes rating

Cosy romantic retreat set amongst rolling countryside in a quiet corner of Teesdale. Ground floor studio accommodation with king-size double bed. WiFi. Barnard Castle 8 miles. (Ref. 927831)

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

7 nights from £328

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A unique converted wheelhouse buried in the Dales village of Barton. Woodburning stove. Traditional character. WiFi. Richmond 7.9 miles; Darlington 5.7 miles; Colburn 9.4 miles. (Ref. 1056697)

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

7 nights from £348

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Pheasant Cottage is a delightful, two-bedroom holiday home resting in Hurst, North Yorkshire. Near Yorkshire Dales National Park. Countryside. Open fire. Richmond 10.4 miles; Leyburn 12.8 miles; Barnard Castle 19.4 miles; Kirkby Stephen 27.9 miles. (Ref. 1140216)

  • Off-road parking
  • Washing machine

7 nights from £479

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

The Barn is a delightful, single-storey holiday cottage situated in Copley near Cockfield, Durham. Woodburning stove. Smart TV. Off-road parking. Bishop Auckland 10 miles; Durham 19.1 miles. (Ref. 1150077)

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

7 nights from £289

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.8

    Good

  • Sykes rating

The Stang Hideaway is a studio-style lodge resting on the Hillcrest Holiday Park in Caldwell, Durham. Romantic. Freestanding bath. Near a National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142458)

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

7 nights from £443

  • 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

7 nights from £439

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An immaculately presented barn conversion with Villroy and Bosh Bathrooms. located outside the village of Staindrop in County Durham. Modern accommodation. Large garden. Staindrop 1.5 miles. Barnard Castle 5 miles. (Ref. 957972)

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

7 nights from £1254

Last booked 2 days ago
See more details
  • Sleeps12
  • Bedrooms6
  • PetsYes

    3.8

    Good

  • Sykes rating

Spacious, single-storey cottage near Gainford, with four bathrooms, WiFi and a wood-fired hot tub. Alpacas and horses on site. Pets welcome. Close to walking and cycling trails. Gainford 1 mile. (Ref. 919938)

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

7 nights from £1086

Last booked 2 days ago
See more details
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A wonderful, detached, 16th-century barn conversion set on a working farm in Ravensworth near Richmond, North Yorkshire. Dog-friendly. Electric flame-effect stove. Character features. Washing machine. Barnard Castle 8.9 miles; Leyburn 14.3 miles. (Ref. 1107452)

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

7 nights from £810

  • 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 £381

Last booked 2 days ago
See more details
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A well-presented stone terrace cottage resting in the sleepy village of Melsonby. Multi-fuel stove. Smart TV. WiFi. Dog-friendly. Modern finish. Yorkshire Dales. (Ref. 974062)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £412