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 126 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
  • 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 £477

Last booked yesterday
See more details
  • 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

7 nights from £440

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

    4.8

    Outstanding

  • Sykes rating

A lovely, two-bedroom home resting in Ovington near Gainford, Durham. Pet-friendly. Close to amenities and river. Near National Park. Woodburning stove. Barnard Castle 7.7 miles; Richmond 11.5 miles; Darlington 12.1 miles. (Ref. 1117841)

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

7 nights from £387

Last booked 9 hours ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A charming single-storey cottage on a working farm, 2.3 miles from the village of Staindrop in Teeside. Spacious accommodation suitable for all family members. WiFi. Excellent walking from the doorstep. Great touring base. Barnard Castle 8 miles. (Ref. 30509)

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

7 nights from £399

Last booked 2 days ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • 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

7 nights from £448

Last booked yesterday
See more details
  • 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

7 nights from £522

  • 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

7 nights from £335

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 £369

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This delightful, terraced, stone cottage is located in Winston, Durham. WiFi. Electric fire. Barnard Castle 6 miles; Darlington 10 miles. (Ref. 998937)

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

7 nights from £341

  • 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

7 nights from £611

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

This beautifully presented, picturesque cottage rests in the town of Barnard Castle in County Durham. Ideal for families. Pet-friendly. Staindrop 6 miles. (Ref. 951368)

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

7 nights from £327

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    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)

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

7 nights from £275

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A luxury cottage in the village of Butterknowle. Modern bathroom. Open plan. Multi-fuel stove. WiFi. Close to Hamsterley Forest and surrounding area. Barnard Castle 10 miles. (Ref. 920251)

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

7 nights from £335

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

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 £323

  • 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

7 nights from £410

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This superb end-terrace stone cottage rests in the market town of Barnard Castle, County Durham. Woodburning stove. Open-plan living. Bishop Auckland 16.1 miles. (Ref. 1014462)

  • Wi-fi
  • Washing machine

7 nights from £481

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • 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

7 nights from £348

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

    4.9

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

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 £288

  • 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

7 nights from £588

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Lovely, single-storey cottage in the grounds of the Grade I listed Walworth Casle Hotel, in the scattered village of Walworth, near Darlington. Open plan living. WiFi. Hot tub. Pet-friendly. Darlington 5 miles. (Ref. 927239)

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

7 nights from £508

Last booked yesterday
See more details

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