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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 167 cottages

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  • Sleeps5
  • Bedrooms2
  • PetsYes
  • Sykes rating

40 Water Lane is a charming pet-friendly cottage in Cromford, Derbyshire, boasting a gas fire, direct access to a footpath and countryside views to enjoy. Matlock Bath 1.9 miles; Matlock 3.2 miles; Bakewell 12.3 miles. (Ref. 949364)

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


for 7 nights $583

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.1

    Good

  • Sykes rating

This fantastic three-bedroom cottage rests in Birchover, Derbyshire. Smart TV. Close to amenities. In the Peak District National Park. Bakewell 5.5 miles; Matlock 6.4 miles. (Ref. 1037666)

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


for 7 nights $744

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.0

    Good

  • Sykes rating

A lovely one-bedroom cottage perched in Bakewell, Derbyshire. Central location. Romantic. En-suite bedroom. Matlock 8.7 miles; Chatsworth 10 miles; Buxton 12.7 miles. (Ref. 1132000)

  • Wi-fi
  • Dishwasher


for 7 nights $606

  • Sleeps7
  • Bedrooms3
  • PetsNo
  • Sykes rating

This fabulous three-bedroom cottage rests in Darley Moor, near Two Dales, Derbyshire. Lakefront. Near a National Park. Bedrooms with en-suites. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129117)

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


for 7 nights $1147

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.7

    Good

  • Sykes rating

A pretty, semi-detached cottage resting within the village of Rowsley. WiFi. Pet welcome. Woodburning stove. Bakewell 4 miles, Buxton 17.3 miles. (Ref. 1025990)

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


for 7 nights $629

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.6

    Good

  • Sykes rating

An inviting three-bedroom cottage resting in Hollingwood, Derbyshire. Child and pet-friendly. Close to amenities. Off-road parking. Brimington 0.7 miles; Barrow Hill 1.4 miles; Chesterfield 3.5 miles; Sheffield 12.7 miles. (Ref. 1076069)

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


for 7 nights $552

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

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A stone-built semi detached cottage on the peaceful Darwin Lake Holiday Village. Three bedrooms with en-suites. Lake and woodland walks on-site. Matlock 3.2 miles. (Ref. 947282)

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


for 7 nights $1180

  • Sleeps5
  • Bedrooms4
  • PetsYes
  • Sykes rating

Havendale is a stunning single-storey holiday home in Chesterfield, Derbyshire, boasting accessible features, a woodburning stove, and an enclosed garden. Matlock 9.5 miles; Chatsworth 10.7 miles; Bakewell 13 miles. (Ref. 1167060)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • 18% off - Mon 5th Jan to 26th Mar 2026


for 7 nights $1602

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2

    Good

  • Sykes rating

A lovely two-bedroom abode resting in Matlock, Derbyshire. Near a National Park. Woodburning stove. Close to amenities. Matlock Bath 1.5 mile; Bakewell 8.6 miles. (Ref. 1113036)

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


for 7 nights $609

  • 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


for 7 nights $1863

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.7

    Good

  • Sykes rating

A neatly-presented two-bedroom cottage resting in Hassop near Calver, Derbyshire. In National Park. Open-plan. Woodburning stove. Off-road parking. Bakewell 2.6 miles; Baslow 3.8 miles; Eyam 4.2 miles. (Ref. 1131996)

  • Wi-fi
  • Off-road parking


for 7 nights $749

  • Sleeps6
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A stylish, end-terrace cottage set in the pretty village of Whitwell in Derbyshire. Loft conversion bedroom. En-suite. Centre of Whitwell. Worksop 5 miles. (Ref. 942650)

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


for 7 nights $798

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This delightful three-bedroom cottage rests in Darley Moor, near Two Dales, Derbyshire. Open-plan. Bedrooms with en-suites. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129127)

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


for 7 nights $1147

  • Sleeps14
  • Bedrooms4
  • PetsNo
  • Sykes rating

Highgate House is a charming holiday home resting in Holmesfield near Dronfield, Derbyshire, with a hot tub, pool table, and enclosed garden. Chesterfield 7.7 miles; Sheffield 9.6 miles. (Ref. 1179440)

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


for 7 nights $2447

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.6

    Good

  • Sykes rating

This pretty three-bedroom dwelling resting in Hassop near Calver, Derbyshire. Private patio. Open fire. Off-road parking. Bakewell 3 miles; Baslow 3.5 miles; Eyam 3.9 miles. (Ref. 1131997)

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


for 7 nights $863

  • Sleeps7
  • Bedrooms3
  • PetsNo
  • Sykes rating

This splendid three-bedroom property is perched in Darley Moor near Two Dales, Derbyshire. Lakeside views. Smart TV. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129130)

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


for 7 nights $1147

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Beautiful barn conversion in a rural location, near the village of Ashover on edge of the Peak District. WiFi. Countryside views across valley. Off-road parking. Electric stove. Matlock 5 miles. (Ref. 1196537)

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


for 7 nights $470

Last booked yesterday
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  • Sleeps20
  • Bedrooms7
  • PetsYes
  • Sykes rating

Five Acres is a large, fun-filled holiday home on the outskirts of pretty market town of Chesterfield, Derbyshire, with a hot tub, sauna and games room. Matlock 9.8 miles; Chatsworth 10.1 miles; Bakewell 13.4 miles; Sheffield 14.8 miles. (Ref. 1166348)

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


for 7 nights $9307

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Dorset Villas is a wonderful Victorian house in Matlock, Derbyshire, boasting a woodburning stove, an enclosed garden and is near pubs and restaurants. Matlock Bath 1.9 mile; Bakewell 8.5 miles. (Ref. 1190845)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $594

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Alexandra Retreat, a charming house resting in Sutton-In-Ashfield, near the Peak District National Park, boasts gas central heating and an enclosed garden. Mansfield 3.1 miles; Chesterfield 11.4 miles. (Ref. 1189857)

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


for 7 nights $599