Winston Holiday Cottages

REFINE SEARCH

Your Winston, Durham search returned 108 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
  • 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 £603

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • 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


for 7 nights £271

Last booked 7 hours ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming three-bedroom terraced cottage resting in Stainton, Durham. Pet-friendly. Enclosed garden. Woodburning stove. Close to amenities. Staindrop 4.2 miles; Richmond 17.2 miles; Darlington 15.7 miles. (Ref. 1063315)

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


for 7 nights £445

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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)

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


for 7 nights £438

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Traditional stone cottage near Staindrop. Beautiful rural location. Underfloor heating. Panoramic views. Comfortable family accommodation. Ideal walking, touring. Barnard Castle 5 miles. (Ref. 16414)

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


for 7 nights £442

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9

    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)

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


for 7 nights £936

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A two-bedroom, stone-fronted cottage resting in Staindrop, Durham. Close to amenities. Woodburning stove. Pet-friendly. Raby Castle 1.7 miles; Barnard Castle 5.5 miles; Durham 19 miles. (Ref. 1097522)

  • Wi-fi


for 7 nights £380

  • 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


for 7 nights £386

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • 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


for 7 nights £725

  • Sleeps6
  • Bedrooms3
  • PetsNo

    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 £479

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

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


for 7 nights £253

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Walworth Castle Lodge is a beautifully presented, pet-friendly, stone-built cottage nestled in the small village of Walworth near Darlington, Durham. Yarm 16.6 miles; Richmond 14.8 miles. (Ref. 1165778)

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


for 7 nights £847

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher


for 7 nights £290

  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 £279

  • 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


for 7 nights £388

  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.6

    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)

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


for 7 nights £294

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Peace Cottage is a beautiful, pet-friendly cottage near Langton in Durham, boasting a woodburning stove, off-road parking, and stunning countryside views. Darlington 9.3 miles; Barnard Castle 9.7 miles; Richmond 15.4 miles; Durham 19.4 miles. (Ref. 1170306)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • £20 off - Mon 27th Oct 2025 to 2nd Jan 2026


for 7 nights £586

Last booked 2 days ago
See more details
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.5

    Outstanding

  • 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. 1179012)

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


for 7 nights £1159

Last booked 4 hours ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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


for 7 nights £452

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A charming cottage in the pretty Durham village of Staindrop. Pet-friendly with woodburning stove. Perfect for touring The Durham Dales. Barnard Castle 5 miles. (Ref. 943949)

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


for 7 nights £436