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 86 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
  • Sleeps19
  • Bedrooms10
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Waterfall Retreat is a stunning, ten-bedroom home resting in Tebay near Orton, Cumbria. Near National Park. Waterfall views. Gym. Pet-friendly. Rural. Kirkby Stephen 10.6 miles; Kendal 14.3 miles; Penrith 18.9 miles; Keswick 35.5 miles. (Ref. 1142474)

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

7 nights from £3984

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Delightful three bedroom cottage with wood-burning stove on the edge of Appleby within walking distance of excellent pub. (Ref. 972250)

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

7 nights from £501

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Larimar is a well-positioned, two-bedroom cottage resting in the heart of Kirkby Stephen, Cumbria. Near National Park. Pet-friendly. Close to amenities. Appleby-in-Westmorland 10.5 miles; Sedbergh 14 miles; Barnard Castle 21.7 miles. (Ref. 1143587)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £389

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

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

Delightful semi-detached stone character cottage located in the hamlet of Keisley near Dufton. Hot tub, pet-friendly, open plan with beams and woodburner. Good walking from the door. Appleby-in-Westermorland 5 miles. (Ref. 945053)

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

7 nights from £466

Last booked 4 hours ago
See more details
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint cottage tucked away in the heart of Kirkby Stephen, Cumbria. Open-plan living. One pet welcome. Central location. Within National Park. Sedbergh 14.1 miles. Hawes 16.6 miles; Kendal 23.5 miles. (Ref. 1059537)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • 10% off - Fri 27th Sep to 20th Dec 2024

  • 10% off - Fri 17th Jan to 14th Feb 2025

7 nights from £357

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Grade II listed Lake District cottage. Peaceful location on side of Wild Boar Fell. Probably one of the best views in Lakeland. Ravenstonedale 4.5 miles. (Ref. 2888)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £585

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming one-bedroom annex resting in Soulby near Kirkby Stephen in Cumbria. Pet-friendly. Off-road parking. Ground-floor living. Appleby-in-Westmorland 8 miles; Sedbergh 16.6 miles; Barnard Castle 25.2 miles. (Ref. 1087465)

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

7 nights from £303

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A wonderful,end-terraced cottage resting in Warcop, Cumbria. Enclosed patio garden. Smart TV. Beautiful views. Children and pet friendly. Penrith 19 miles, Sedbergh 19.1 miles, Kendal 28.5 miles; Reeth 30.8 miles. (Ref. 1051899)

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

7 nights from £419

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A splendid reverse-level cottage nestled at the heart of Kirkby Stephen, Cumbria. Pet-friendly. Open-plan living space. Central location. Ravenstonedale 4.7 miles; Appleby-in-Westmorland 10.5 miles; Barnard Castle 21.7 miles. (Ref. 1059546)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • 10% off - Fri 27th Sep to 20th Dec 2024

  • 10% off - Fri 17th Jan to 14th Feb 2025

7 nights from £357

  • Sleeps2
  • Bedrooms1
  • PetsYes
  • Sykes rating

A romantic first-floor apartment resting in Thwaite, North Yorkshire. Open-plan. En-suite. Off-road parking. Bainbridge 8.6 miles; Kirkby Stephen 12.4 miles; Barnard Castle 20.5 miles. (Ref. 1162644)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £299

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A wonderful three-bedroom mid-terrace cottage resting in Great Asby, Cumbria. Woodburning stoves. Enclosed garden. In a National Park. Views of the stream. Penrith 19 miles. (Ref. 1103091)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £496

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint lodge nestled on a small holding near Appleby-in-Westmorland, Cumbria.Sykes GEM Silver Winner of Best Newcomer 2023. Pet-friendly. Romantic. Countryside views. Woodburning stove. Penrith 17.9 miles; Barnard Castle 22.2 miles; Carlisle 36.4 miles. (Ref. 1107447)

  • Wi-fi
  • Off-road parking

7 nights from £326

Last booked yesterday
See more details
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    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 £399

  • 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 £394

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming cottage set within the village of Kirkby Stephen, Cumbria. Romantic dwelling. Open-plan living. Close to amenities. Ravenstonedale 4.8 miles; Sedbergh 14.1 miles; Kendal 23.5 miles. (Ref. 1059543)

  • Wi-fi
  • Dishwasher
  • 10% off - Fri 27th Sep to 20th Dec 2024

  • 10% off - Fri 17th Jan to 14th Feb 2025

7 nights from £357

  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Charming semi-detached cottage set in a rural location, close to Kirkby Stephen in Cumbria. Woodburner. Original features. Lovely views. Kirkby Stephen 3 miles. (Ref. 23932)

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

7 nights from £689

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A delightful, stone-built cottage resting on the outskirts of Middleton-in-Teesdale. Hot tub. Pet-friendly. Woodburning stove. Barnard Castle 12.3 miles. (Ref. 974492)

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

7 nights from £900

  • 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 £347

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Band Room is a welcoming, reverse-level abode nestled into Kirkby Stephen, a town in Cumbria. Open-plan. Woodburning stove. En-suite. Near shop. Appleby-in-Westmorland 10.5 miles; Sedbergh 14.1 miles; Barnard Castle 21.7 miles; Penrith 26.6 miles; Ree (Ref. 1156376)

  • Wi-fi
  • Ground floor bedroom

7 nights from £370

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This traditional, stone cottage rests in Kirkby Stephen. Cumbria. Near amenities and the River Eden. Off-road parking. Enclosed garden. Near National Park. Kendal 23.5 miles. (Ref. 1133025)

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

7 nights from £472