Winston Holiday Cottages

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Your Winston, Durham search returned 106 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1

    Good

  • Sykes rating

Ivy Cottage is a delightful cottage 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. 1147943)

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


for 7 nights €397

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A delightful mid-terrace cottage settled just outside the centre of Richmond, North Yorkshire. Open-plan. Dog-friendly. Leyburn 9.3 miles; Barnard Castle 15.5 miles. (Ref. 1050331)

  • Wi-fi
  • Off-road parking


for 7 nights €420

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

This stone-built cottage is located in the village of Romaldkirk in County Durham. Woodburner. Exposed stonework. Barnard Castle 6 miles. Richmond 14 miles. (Ref. 970654)

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


for 7 nights €546

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

An early nineteenth century stone-built cottage in the peaceful, picturesque 'Maypole' village of Ovington. Perfect for a well-earned romantic break. Barnard Castle 6 miles. Richmond 12 miles. (Ref. 935226)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights €367

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

This superb stone cottage is based in North Yorkshire, England. WiFi. Open fire. Barnard Castle 10 miles; Leyburn 12 miles. (Ref. 999973)

  • Wi-fi
  • Washing machine


for 7 nights €491

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A wonderful terraced property resting in Richmond, Yorkshire. Off-road parking. Electric fire. Pet-friendly. Barnard Castle 15.5 miles. (Ref. 1053052)

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


for 7 nights €420

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Old Assembly Rooms is a first-floor apartment settled into the town of Bishop Auckland, Durham. Close to a shop and a pub. Near AONB. Durham 10.7 miles; Barnard Castle 14.8 miles; North Pennines AONB 16 miles. (Ref. 978899)

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


for 7 nights €560

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

A splendid, three-bedroom holiday home resting in Richmond, North Yorkshire. Woodburning stove. Close to amenities. Dishwasher. Leyburn 9.1 miles; Barnard Castle 15.1 miles. (Ref. 1038592)

  • Wi-fi
  • Dishwasher


for 7 nights €761

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.0

    Good

  • Sykes rating

Rose Cottage is an end-terrace cottage located on a holiday park, resting in Caldwell near Eppleby, Durham. Romantic. Ground-floor living. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142456)

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


for 7 nights €370

  • 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
  • Washing machine


for 7 nights €385

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

An exceptional stable conversion resting on the outskirts of Barnard Castle in North Yorkshire. Single-storey accommodation. Open-plan living. WiFi. Hot tub. Middleton in Teesdale 12.8 miles; Richmond 15 miles. (Ref. 1078952)

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


for 7 nights €1530

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

This attractive, mid-terrace cottage sits in the heart of Richmond, Yorkshire. Open-plan. Woodburning stove. Cinema room. Catterick 5.4 miles; Leyburn 9.1 miles; Barnard Castle 14.3 miles. (Ref. 1038663)

  • Wi-fi


for 7 nights €470

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • 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


for 7 nights €791

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Artist’s Cottage is a delightful cottage in Richmond, North Yorkshire, well-positioned to an array of attractions and boasting a woodburning stove. Leyburn 9 miles; Darlington 13 miles; Barnard Castle 15.1 miles; Middlesborough 28.7. (Ref. 1163443)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights €571

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.6

    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


for 7 nights €483

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.3

    Good

  • Sykes rating

Woodland View is a quaint, single-storey abode resting in the countryside of Copley, a peaceful village in Durham. Romantic. Off-road parking. Smart TV. Cockfield 3.4 miles; Bishop Auckland 9.7 miles; Durham 19.1 miles. (Ref. 1150078)

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


for 7 nights €290

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.8

    Good

  • Sykes rating

Willow Cottage is a delightful, two-bedroom abode resting in Caldwell near Eppleby, Durham. Pet-friendly. Enclosed garden. Near National Park. Barnard Castle 7.4 miles; Richmond 11 miles; Darlington 11.7 miles. (Ref. 1142455)

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


for 7 nights €429

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9

    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


for 7 nights €367

  • 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
  • €23 off - Mon 27th Oct 2025 to 2nd Jan 2026


for 7 nights €689

  • Sleeps8
  • Bedrooms4
  • PetsYes

    3.8

    Good

  • Sykes rating

A fantastic, terraced cottage perched in the heart of Barnard Castle, County Durham. Dog-friendly. Pool table. Close to amenities. Near a National Park. Off-road parking. Staindrop 5.8 miles; Richmond 14.8 miles; Darlington 15.7 miles. (Ref. 1062818)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Games room


for 7 nights €761