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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 167 cottages

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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A fantastic five-bedroom detached house resting in Bakewell, Derbyshire. Pet-friendly. Woodburning stove. Off-road parking. Chatsworth 9.7 miles; Matlock 8.6 miles; Buxton 13.4 miles. (Ref. 921800)

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

7 nights from £1457

Last booked yesterday
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  • Sleeps8
  • Bedrooms5
  • PetsNo
  • Sykes rating

Old Manor House is a charming and traditonal holiday home located in the village of Cutthorpe in Derbyshire with two woodburning stoves and large gardens. Chatsworth 9 miles; Bakewell 10.5 miles; Matlock 11.9 miles. (Ref. 1169415)

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

7 nights from £1439

  • Sleeps14
  • Bedrooms6
  • PetsYes
  • Sykes rating

Hallfield Hall is a stunning house situated in Shirland, Derbyshire, boasting a hot tub, bar, snooker table, games room, cinema room, and enclosed garden. Alfreton 2.4 miles; Matlock Bath 8.4 miles; Bakewell 15.1 miles; Derby 15.6 miles. (Ref. 1169570)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Games room

7 nights from £2403

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A truly breath-taking converted water tower on the outskirts of Bolsover, Derbyshire. Woodburning stove. Stylish and contemporary. Romantic. Off-road parking. 6 acres of land. Chesterfield 7.7 miles; Sherwood Forest 9.7 miles; Sheffield 16.6 miles. (Ref. 1116427)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £1019

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This studio property is set in the heart of Bakewell, Peak District National Park. Modern interior. Charming courtyard. Central location. (Ref. 989667)

  • Wi-fi

7 nights from £376

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Mid-terrace cottage based in the market town of Dronfield in Derbyshire. Woodburning stove. Enclosed garden. Sheffield 7.2 miles. (Ref. 1035228)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £452

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Oakwood Lodge is a charming, detached holiday home in Tansley, Derbyshire. Countryside views. Near the Peak District National Park. Pet-friendly. Matlock 1.7 miles; Bakewell 10.2 miles; Derby 18.4 miles. (Ref. 1147569)

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

7 nights from £670

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A detached farmhouse located in the village of Hathersage in Hope Valley. Woodburners. Pet-friendly. Four bedrooms. Castleton 5 miles. Curbar 5 miles. (Ref. 952361)

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

7 nights from £1262

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A lovely apartment in the centre of Eyam village in the Peak District National Park. Ideal for couples wishing to explore this historic area. Beautiful countryside with fabulous walks. Bakewell 7 miles. (Ref. 946764)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £331

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This traditional mid-terrace property rests at the heart of the Peak District. Brilliant base for walking. Private enclosed courtyard. Calver 1 mile. (Ref. 967600)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £643

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This charming, four-bedroom home rests in Sheffield, South Yorkshire. Near a National Park. Smart TV. Off-road parking. Enclosed garden. Chesterfield 9.6 miles; Doncaster 21.9 miles. (Ref. 1134637)

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

7 nights from £636

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A charming two-bedroom semi-detached house resting in Ashover, Derbyshire. Family-friendly. Smart TV. Near a river. Matlock 4.6 miles, Chesterfield 6.7 miles. (Ref. 1072527)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £415

  • 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

7 nights from £1309

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Alfreton Cottage is a fabulous, dog-friendly holiday cottage in Newton near Alfreton, Derbyshire near the Peak District. South Normanton 1.6 miles; Oakerthorpe 5.2 miles; Kirkby-in-Ashfield 5.3 miles (Ref. 1162722)

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

7 nights from £388

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Matlock Maisonette is situated in Matlock in Derbyshire. Duplex apartment. Far-reaching views. Stunning terrace. Central location. Allocated parking. Bakewell 8.6 miles. Alfreton 9.2 miles. Sheffield 22.5 miles. (Ref. 1153088)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £616

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A converted church resting within Birchover, near Winster. Pet-friendly. WiFi. Pub within 0.2 miles. Matlock 6.5 miles. (Ref. 1005440)

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

7 nights from £556

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A contemporary first-floor apartment in Clay Cross, Derbyshire. Pet-friendly. Countryside views. Close to amenities. Smart TV. Chesterfield 5.1 miles; Matlock 7.8 miles; Peak District National Park 9.6 miles. (Ref. 1065378)

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

7 nights from £579

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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
  • 5% off - Mon 7th Apr to 3rd May 2025

7 nights from £520

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Character terraced property, originally part of stone barn just outside village of Barlow. With open plan living area and woodburner. Ideal base for walkers and cyclists. Barlow 1 mile. (Ref. 939317)

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

7 nights from £368

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Ty Gambo is a holiday house resting in the village of Oker in Derbyshire. Hot tub. Woodburning stove. Smart TV. Off-road parking. In National Park. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1142883)

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

7 nights from £1373