Winster Cottages

Your Winster, Derbyshire search returned 193 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Chimney Cottage is a charming pet-friendly cottage in Winster, Derbyshire, with sublime countryside views to admire all around. Matlock 5.5 miles; Bakewell 6.7 miles. (Ref. 1172633)

  • Wi-fi
  • Baby-friendly
  • 5% off - Thu 7th May to 30th Jun 2026


for 7 nights €661

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

Deeley House is a charming, Georgian-period home set on the edge of the pretty Peak District National Park in Darley Dale, Derbyshire, welcoming pets. Matlock 3.7 miles; Bakewell 4.7 miles; Ashbourne 15.8 miles. (Ref. 1167997)

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


for 7 nights €1109

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A charming stone cottage (bookable with The Hayloft - 1063737) situated at the superb village of Winster in Derbyshire. Countryside views. Underfloor heating. Woodburning stove. Matlock 5.3 miles; Bakewell 6.4 miles; Chesterfield 12.5 miles. (Ref. 1051655)

  • Wi-fi


for 7 nights €537

  • Sleeps18
  • Bedrooms7
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A brilliant, detached house resting on a farm in Middleton near Youlgreave, Derbyshire. Ample off-road parking. Open fire and woodburning stove. Hot tub. Winster 4.6 miles; Bakewell 6.6 miles; Matlock 9.8 miles. (Ref. 1079762)

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


for 7 nights €2616

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Tom's Barn is a romantic home in the village of Parwich, Derbyshire, boasting a woodburning stove, an open-plan layout, a whirlpool bath and allows pets. Ashbourne 7.3 miles; Bakewell 11.8 miles. (Ref. 1168384)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher


for 7 nights €515

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A pretty white-washed cottage set in the village of Middleton, within the Peak District. Romantic dwelling. Woodburning stove. Pet-friendly. Matlock 4.4 miles; Ashbourne 9.9 miles; Bakewell 11.2 miles. (Ref. 1040665)

  • Wi-fi
  • Washing machine


for 7 nights €428

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Superb first floor apartment in Matlock. Individually styled, open plan accommodation, close to amenities. National Park within easy reach. Bakewell 8 miles. (Ref. 2401)

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


for 7 nights €403

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This charming semi-detached cottage rests in Tansley, Derbyshire. Off-road parking. Woodburning stove. Pet-free. Garden with furniture. Matlock 1.7 miles. (Ref. 1061197)

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


for 7 nights €636

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Beautiful ground floor barn conversion surrounded by wonderful Derbyshire countryside, close to Wirksworth and Carsington Water. Character cottage with woodburner and beams. Wirksworth 4 miles. (Ref. 16787)

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


for 7 nights €460

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4

    Good

  • Sykes rating

Character detached cottage in village of Biggin. Two sitting rooms, one with woodburner. Two bedrooms, as well as a cot room and family bathroom. Extensive enclosed lawned gardens. Plenty of walking and cycling opportunities. Ashbourne 10 miles. (Ref. 952294)

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


for 7 nights €374

Last booked 3 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

This charming terraced cottage sits in the Derbyshire town of Matlock. Over three floors. Pet-friendly. WiFi. Matlock Bath 1 mile. (Ref. 963763)

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


for 7 nights €465

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Lovely detached bungalow close to centre of the Derbyshire market town of Matlock. Edge of Peak District National Park. Bakewell 8 miles. (Ref. 5689)

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


for 7 nights €597

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely romantic cottage with some wonderful features, including stone fireplace with woodburner. WiFi. A short walk to village amenities, making a perfect romantic break. Matlock 3 miles. (Ref. 923214)

  • Wi-fi


for 7 nights €388

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A delightful, terraced cottage in the heart of Bakewell, Derbyshire. Within Peak District National Park. Romantic. Permit parking. Enclosed patio. Pet-friendly. Chatsworth 9.7 miles; Buxton 12.4 miles; Sheffield 17.3 miles. (Ref. 1134730)

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


for 7 nights €688

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.1

    Good

  • Sykes rating

Orchard View is a magnificent, Grade II-listed farmhouse in the pretty village of Parwich, Derberyshire, with a woodburning stove and a four-poster bed. Ashbourne 6.8 miles; Bakewell 11.7 miles. (Ref. 1175664)

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


for 7 nights €842

Last booked 5 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A delightful cottage by the village of Hartington, Derbyshire. Charming interior. Ideal for couples. Bakewell 10 miles; Buxton 10 miles. (Ref. 996810)

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


for 7 nights €313

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Douglas's Barn is a welcoming house in the village of Parwich, Derbyshire boasting an open-plan layout, electric fire, jacuzzi bath and allows pets. Ashbourne 7.3 miles; Bakewell 11.8 miles. (Ref. 1168385)

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


for 7 nights €487

  • Sleeps18
  • Bedrooms9
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Sensational, detached conversion of the Arkwright’s Grade II listed former corn mill in Cromford. En-suite facilities. Three kitchens and sitting rooms. Feature beams and stonework. Lawned garden with furniture, mill pond and waterfall. Matlock 3 miles. (Ref. 17888)

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


for 7 nights €2562

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

Roseville is a charming, 18th-century property resting in the riverside town of Cromford, Derbyshire, Close to a National Park, and with a hot tub. Matlock 3 miles; Peak District National Park 7.3 miles; Bakewell 11 miles. (Ref. 1155096)

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


for 7 nights €822

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

Grade II listed Georgian cottage nestled in Bakewell. WiFi. Open-plan living. Immaculate finish. Chatsworth 4 miles; Matlock 8 miles. (Ref. 993152)

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


for 7 nights €1374