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.

Winton Holiday Cottages

REFINE SEARCH

Your Winton, Cumbria search returned 89 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
  • Sleeps12
  • Bedrooms6
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This detached sandstone cottage rests in Dufton, near Appleby-in-Westmorland in Cumbria. Spacious. Woodburning stove. Large garden. Penrith 14.3 miles; Middleton-in-Teesdale 25.4 miles. (Ref. 1076512)

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

7 nights from £742

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

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

A quaint, reverse-level cottage resting amongst the countryside beauty of Cumbria, in close reach of the historic town of Appleby-in-Westmorland. Characterful. En-suites. Multi-fuel stove. Smart TV. WiFi. Kirkby Stephen 7.7 miles; Penrith 18.7 miles. (Ref. 1039951)

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

7 nights from £520

  • Sleeps13
  • Bedrooms6
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A remarkable stone-built holiday home with annexe resting in the peaceful hamlet of Brackenber, Cumbria. En-suites. Ground-floor living. Countryside views. Appleby-In-Westmorland 2.9 mile; Penrith 16.5 miles; Pooley Bridge 19.2 miles. (Ref. 926047)

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

7 nights from £1418

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Lovely stone-built, semi-detached farmhouse conversion on hillside. Picturesque area. WiFi. Original features, open fire and spacious garden with small beck. Ravenstonedale 4.5 miles. (Ref. 10542)

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

7 nights from £383

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Delightful, stone-built, single-storey cottage near Soulby. Ideal base for touring. Set in a peaceful countryside location, just three miles from Kirkby Stephen. (Ref. 2253)

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

7 nights from £301

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A character cottage based in the heart of the small town of Brough. Ideal for families or couples. Patio/garden. Kirkby Stephen 4.3 miles. (Ref. 1033651)

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

7 nights from £374

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Semi-detached Cumbria cottage, on working farm in Newbiggin-on-Lune. Upside down accommodation, play area. Kirkby Stephen 6 miles. (Ref. 17243)

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

7 nights from £310

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

    4.7

    Outstanding

  • Sykes rating

A lovely two-bedroom holiday home resting in Kirkby Stephen, Cumbria. Private garden. Pet-free. Smart TV. Off-road parking. Near a National Park. Appleby-in-Westmorland 10.3 miles; Sedbergh 14.5 miles; Barnard Castle 21.9 miles (Ref. 1074852)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £493

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This immaculate holiday cottage rests in Kirkby Stephen in Cumbria. On the fringes of the Lake District and Yorkshire Dales National Parks. Woodburning stove. Sauna. Barnard Castle 21.9 miles; Kendal 23.5 miles. (Ref. 1057074)

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

7 nights from £705

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A beautiful 18th Century barn conversion which has been lovingly restored to provide high standard accommodation for friends and families wishing to relax and explore some of the most stunning areas in the country. Appleby-in-Westmorland 4 miles. (Ref. 935012)

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

7 nights from £459

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Lovely mid-terrace nestled in the heart of Appleby-in-Westmorland. Beautiful gardens. WiFi. Pet-friendly. Lake District National Park; North Pennines AONB. (Ref. 950945)

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

7 nights from £336

Last booked 2 days ago
See more details
  • Sleeps5
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

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

This semi-detached cottage lies in the small village of Great Asby near Appleby-In-Westmorland. Renovated barn. Underfloor heating. En-suite. Kirkby Stephen 7.7 miles; Penrith 18.7 miles. (Ref. 1044804)

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

7 nights from £623

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A stylish, single-storey abode perched in Flakebridge near Appleby-In-Westmoreland, Cumbria. Dog-friendly. Near an AONB. Off-road parking. Smart TV. Penrith 15.2 miles. (Ref. 1133509)

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

7 nights from £577

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Charming stone-built cottage nestled in the heart of Keld, near the village of Muker in North Yorkshire. TV with FreeSat. WiFi. Cosy/romantic. Yorkshire Dales National Park. (Ref. 975668)

  • Wi-fi
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £344

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A superb barn conversion resting on a working farm, near Kirkby Stephen. En-suite bathrooms. WiFi. Rural location. Appleby-in-Westmorland 10.8 miles; Barnard Castle 20.1 miles. (Ref. 1052158)

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

7 nights from £489

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

The Hayloft is a charming, stone-fronted cottage perched in Keisley near Appleby-In-Westmorland, Cumbria. Countryside views. In an AONB. Smart TV. Penrith 16.3 miles. (Ref. 1138662)

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

7 nights from £821

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A sleek, single-storey abode set in within a shared courtyard in the village of Flakebridge near Appleby-In-Westmorland, Cumbria. Smart TV. High-end. Off-road parking. Penrith 15.2 miles. (Ref. 1133513)

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

7 nights from £445

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Oak Cottage is a homely, reverse-level cottage in Appleby-in-Westmorland, Cumbria. Enclosed garden. Near Lake District National Park. Pet-friendly. Askham 13.2 miles; Penrith 13.9 miles; Glenridding 25.6 miles. (Ref. 1143735)

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

7 nights from £341

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

Spacious annexe to Brackenber Hall, situated down a private country lane on the outskirts of Appleby-in-Westmorland, Cumbria. Dog-friendly. Off-road parking. Enclosed garden with patio furniture. Penrith 14 miles. (Ref. 983283)

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

7 nights from £432

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Good

  • Sykes rating

This converted barn sits close to the charming village of Muker in North Yorkshire. Open-plan living. In Yorkshire Dales National Park. Excellent walking and cycling location. (Ref. 984484)

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

7 nights from £334