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 116 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)
  • Guest Rated (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    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

7 nights from €728

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    5.0

Superb two bedroom cottage with a multi-fuel stove and panoramic countryside views. Bike storage, patio with furniture and BBQ. Barnard Castle 2 miles. (Ref. 21862)

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

7 nights from €401

Last booked 4 hours ago
See more details
  • 10 Guests
  • 5 Bedrooms
  • Pets Yes

    4.6

    Sykes Rating

The Farm House, a charming holiday cottage resting by Aldbrough St. John, Yorkshire. Hot tub. Smart TV. Woodburning stove. Pet-friendly. Off-road parking. Richmond 8.2 miles; Darlington 8.3 miles; Middlesbrough 24.1 miles. (Ref. 1144500)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from €2188

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.3

    Sykes Rating

The Arches is a beautifully-presented holiday home set on a working farm in Caldwell near Eppleby in North Yorkshire. En-suite bedrooms. Countryside views. Richmond 9.7 miles. (Ref. 1147631)

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

7 nights from €765

Last booked 2 days ago
See more details
  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    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

7 nights from €584

  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    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 €500

  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    4.7

    Sykes Rating

A fantastic four-bedroom semi-detached barn conversion resting in Marwood, Durham. Pet-friendly. Dale views. Hot tub. Original features. Off-road parking. Smart TVs. Staindrop 8.8 miles; Darlington 20.5 miles; Richmond 20.6 miles. (Ref. 16526)

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

7 nights from €1109

Last booked yesterday
See more details

7 nights from €447

Last booked yesterday
See more details
  • 6 Guests
  • 2 Bedrooms
  • Pets Yes

    4.7

    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

7 nights from €475

Last booked 2 days ago
See more details
  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    4.6

    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
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €1599

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

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

7 nights from €353

  • 7 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    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 €990

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A well-positioned two-bedroom cottage resting in Ingleton near Gainford, Durham. Hot tub. Countryside views. Woodburning stove. Pet-friendly. Open-plan. Raby Castle 4.1 miles; Barnard Castle 8.8 miles; Darlington 8.5 miles. (Ref. 1101654)

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

7 nights from €552

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    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 €591

Last booked 2 days ago
See more details
  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    Sykes Rating

School House is a stunning, stone-built home resting in the countryside of Hurst near Reeth, North Yorkshire. Near National Park. Woodburning stove. Countryside views. Reeth 2.8 miles; Richmond 10.4 miles; Yorkshire Dales National Park 15.2 miles. (Ref. 1151648)

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

7 nights from €1001

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.3

    Sykes Rating

Bowes Hideaway, a studio-style lodge perched on the Hillcrest Holiday Park in Caldwell, Durham. Hot tub. Romantic. Freestanding bath. Near a National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142457)

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

7 nights from €612

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A charming stone cottage tucked away in the village of Staindrop in County Durham. Pet-friendly. Woodburning stove. Smart TV. Close to amenities. Gainford 4.5 miles; Barnard Castle 5.8 miles. Please contact us if you wish to book between 23 and 28 April o (Ref. 981909)

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

7 nights from €862

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.8

    Sykes Rating

Modern detached brick-built bungalow on edge of popular market town of Richmond. Comfortable accommodation with sun-trap garden area. Barnard Castle 10 miles. (Ref. 249)

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

7 nights from €401

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    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)

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

7 nights from €538

  • 2 Guests
  • 1 Bedroom
  • Pets No

    5.0

    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 €308