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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.8

    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

7 nights from £458

  • Sleeps4
  • Bedrooms2
  • PetsNo

    Sykes Rating

62 Heritage Dr is a homely semi-detached house in Clowne, Derbyshire, EV charging, a travel cot and highchair available, and lovely views of the village. Chesterfield 8.8 miles; Sutton-in-Ashfield 12.1 miles; Sheffield 18.8 miles. (Ref. 1166380)

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

7 nights from £440

  • Sleeps12
  • Bedrooms6
  • PetsNo

    Sykes Rating

56 Riverdale Road in Sheffield, South Yorkshire is a substantial, semi-detached property. Family-friendly. Spacious. Great location. Gardens. Park views. Chesterfield 13.1 miles. Bakewell 15.6 miles. Doncaster 24.8 miles. (Ref. 1152394)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £1362

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

A beautiful terraced miners cottage resting in Stanfree, Derbyshire. Electric woodburning stove. Close to Peak District National Park. Pet-friendly. Chesterfield 7 miles; Sheffield 15.4 miles. (Ref. 1112748)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £340

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.6

    Sykes Rating

8 Inns Lane is a delightful, three-bedroom holiday home resting in South Wingfield, Derbyshire. Near a National Park. Close to pub. Off-road parking. Pet-free. Matlock 6.4 miles. (Ref. 1142655)

  • Wi-fi
  • Washing machine

7 nights from £358

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Sykes Rating

The Botanical Flat 1, a charming, three-bedroom apartment in Sheffield, South Yorkshire. Pet-friendly. Close to amenities. Near Botanical Gardens & Peak District National Park. Sheffield 2.1 miles; Matlock 21.4 miles; Leeds 37.1 miles. (Ref. 1148552)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £526

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

    Sykes Rating

Churchside House is a charming, three-bedroom holiday cottage resting in Matlock, Derbyshire. Close to amenities. Near a National Park. Electric fire. Matlock Bath 2.8 mile; Bakewell 8.9 miles. (Ref. 1105058)

  • Dishwasher
  • Washing machine
  • 5% off - Sun 29th Jun to 22nd Jul 2025

7 nights from £502

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.0

    Sykes Rating

This beautifully-presented cottage is nestled in Bakewell, Derbyshire. Central location. Smart TV. En-suite bedroom. Matlock 8.7 miles; Chatsworth 10 miles; Buxton 12.7 miles. (Ref. 1131999)

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

7 nights from £766

Last booked yesterday
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  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.5

    Sykes Rating

Spacious end-terrace cottage near village of Barlow. Set over three floors with woodburner and play room. Ideal base for a relaxing break. Barlow 1 mile. (Ref. 12587)

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

7 nights from £372

  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.7

    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

7 nights from £434

  • Sleeps7
  • Bedrooms2
  • PetsNo

    4.3

    Sykes Rating

First floor of former carriage house in the Derbyshire village of Cromford. World Heritage Site. Listed building. Open-plan. Exposed stone and beams. En-suites. (Ref. 953526)

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

7 nights from £516

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.8

    Sykes Rating

A stunning two-bedroom cottage resting in Bakewell, Derbyshire. Central location. Woodburning stove. Off-road parking. Matlock 8.7 miles; Chatsworth 10 miles; Buxton 12.7 miles. (Ref. 1131998)

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

7 nights from £519

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.1

    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

7 nights from £616

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.6

    Sykes Rating

Magnificent detached conversion with unusual layout near Baslow. Character accommodation. Breathtaking views, private hot tub and sauna. Near Chatsworth House. Bakewell 9 miles. (Ref. 2674)

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

7 nights from £729

Last booked yesterday
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  • 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

7 nights from £1045

  • Sleeps5
  • Bedrooms3
  • PetsYes

    Sykes Rating

15 Calton View is a lovely semi-detached, pet-friendly house resting in the market town of Bakewell in Derbyshire and is near the local shop and pub. Matlock 8.8 miles; Chatsworth 10.2 miles; Buxton 12.8 miles. (Ref. 1073727)

  • Wi-fi
  • Washing machine

7 nights from £534

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    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

7 nights from £1045

  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8

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

7 nights from £924

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.3

    Sykes Rating

Beautiful stone semi-detached cottage located near the rural village of Two Dales in Derbyshire. Lakeside views. Dog friendly. On-site fishing. Shop and pub 2.5 miles. (Ref. 981396)

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

7 nights from £795

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.0

    Sykes Rating

A delightful, ground floor apartment situated on the edge of Calver in the centre of the Peak District. Electric fire. Communal garden with bench. Off-road parking. Bakewell 5.5 miles. (Ref. 1077415)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £341