Winster Cottages

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Your Winster, Derbyshire search returned 182 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A characterful chocolate box cottage, resting in Youlgreave, Derbyshire. Original features. Pet-friendly. Close to amenities. Woodburning stove. Bakewell 3.5 miles; Buxton 13.2 miles; Leek 18.4 miles. (Ref. 1106936)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €496

  • 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 €2519

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely barn conversion with wonderful views. Cosy and welcoming, large garden. Walks from the door. Wirksworth 3 miles. (Ref. 18971)

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


for 7 nights €360

  • 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 €2499

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • 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
  • €1632 off - Sat 3rd Jan to 10th Jan 2026


for 7 nights €872

  • 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 €407

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Cosy stone-built barn conversion on the owners' working livestock farm, two miles from Matlock. Large garden, pet-friendly. Walks from the doorstep. Opposite Matlock Golf Club. Bakewell 10 miles. (Ref. 929053)

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


for 7 nights €396

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Cosy Peak District cottage, on a working dairy farm with fantastic countryside views. Ideal touring base for couple or family. Parwich 3 miles. (Ref. 4474)

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


for 7 nights €365

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Bear Cottage, a pretty terraced cottage situated in the town of Cromford in Derbyshire, close to a shop and a pub, and the Peak District National Park. Matlock Bath 1.2 miles; Wirksworth 1.9 miles; Peak District National Park 7.2 miles. (Ref. 1100050)

  • Wi-fi
  • Baby-friendly


for 7 nights €417

Last booked 2 days ago
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  • 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 - Fri 31st Oct to 23rd Dec 2025

  • 5% off - Sat 3rd Jan to 31st Jan 2026


for 7 nights €614

Last booked 2 days ago
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  • Sleeps11
  • Bedrooms6
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Character barn conversion, positioned near the market town of Wirksworth, on the edges of the Peak District. WiFi. Off-road parking. Enclosed garden. Games room. Family-friendly. Matlock 5.4 miles. (Ref. 1179320)

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


for 7 nights €1225

  • Sleeps8
  • Bedrooms4
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Gardeners Cottage, a glorious reverse-level cottage in the hamlet of Hopton, boasting an open-plan layout, en-suite facilities. Carsington 0.2 miles; Wirksworth 2.3 miles; Bakewell 12.3 miles; Ashbourne 7 miles. (Ref. 1170350)

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


for 7 nights €1096

  • 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 €370

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

This charming detached barn conversion rests in the heart of Wirksworth, in Derbyshire Dales. WiFi. Pet-friendly. Matlock 4.6 miles; Ashbourne 9.1 miles. (Ref. 1002611)

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


for 7 nights €684

  • 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 €382

  • 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 €666

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

26 Main Street is a pet-friendly holiday cottage situated in the village of Middleton in Derbyshire set over three floors with a woodburning stove. Matlock 4.7 miles. (Ref. 1166934)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €465

  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Lovely, semi-detached cottage in the heart of Middleton near Wirksworth and Cromford. Feature beams. En-suite facilities. Patio with furniture. Great base for walking. Wirksworth 1.5 miles. (Ref. 12183)

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


for 7 nights €466

  • 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 €1351

  • 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 €475