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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps9
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Rowtor is a wonderfully-adorned barn conversion residing in Birchover near Winster, Derbyshire. In the Peak District National Park. Study. Mezzanine study. Ground-floor bedrooms and open-plan living. Character. Bakewell 5.6 miles; Matlock 6.3 miles. (Ref. 1120844)

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

7 nights from £742

  • 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

  • Sleeps6
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A former carriage house in the market town of Dronfield. Stunning beams, en-suite, very comfortable accommodation.WiFi. Three miles from the Peak District National Park and within walking distance of every amenity. Sheffield 7 miles. (Ref. 931313)

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

7 nights from £576

  • Sleeps3
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Lydgate Cottage is an original cottage sitting in the heart of Eyam, Derbyshire. Hot tub. Pet-friendly. Woodburning stove. Near amenities. In National Park. Tideswell 5.2 miles; Bakewell 6.8 miles. (Ref. 1066992)

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

7 nights from £730

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint, mid-terrace cottage settled in the village of Matlock, Derbyshire. Woodburner. Enclosed garden. Scenic location. Bakewell 4.7 miles; Matlock Bath 5 miles. (Ref. 1094150)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • £73 off - Sat 14th Jun to 21st Jun 2025

  • £82 off - Sat 28th Jun to 5th Jul 2025

7 nights from £553

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Temperance Croft is a charming, single-storey holiday cottage resting in the quaint little village of Wadshelf in Derbyshire which is ideal for couples. Chatsworth 5.4 miles; Bakewell 8.3 miles; Matlock 9.1 miles. (Ref. 1155313)

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

7 nights from £382

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Causeway Hideaway is a delightful, single-storey annexe resting in Dore, South Yorkshire. Romantic. Close to amenities. Stylish. Near National Park. Sheffield 5.4 miles; Chesterfield 11.7 miles. (Ref. 1133830)

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

7 nights from £450

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

The Bottling Shed, a wonderful holiday retreat lying in the scenic Peak District in Matlock, Derbyshire. Romantic retreat. Hot tub. Open-plan. Balcony. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1048671)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from £520

  • 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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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Converted chapel. One en-suite bedroom. Private patio with furniture. Woodburning stove. Crich 3.3 miles. Matlock 4 miles. (Ref. 924332)

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

7 nights from £386

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This lovely little stone cottage sits in the Derbyshire village of Cromford. Near Peak District National Park. WiFi. Matlock 3 miles. (Ref. 981522)

  • Wi-fi
  • Off-road parking

7 nights from £309

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Number 4 Westmoreland is a stylish ground-floor apartment with off-road parking, close to the Peak District in the village of Two Dales, Derbyshire. Matlock 2.5 miles; Bakewell 6.1 miles. (Ref. 1160185)

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

7 nights from £425

Last booked yesterday
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  • 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

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.6

    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
  • £352 off - Fri 25th Jul to 1st Aug 2025

  • £449 off - Fri 8th Aug to 15th Aug 2025

7 nights from £1262

Last booked 2 days ago
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  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming duplex apartment set in a Grade II listed building in Cuckney, Nottinghamshire. Character features. Off-road parking. En-suite bathrooms. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116401)

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

7 nights from £739

  • 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

  • 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

7 nights from £371

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

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A lovely, detached Baslow cottage with original features and character charm. A cosy, welcoming Baslow cottage close to the Chatsworth Estate, beautiful walks and nearby Bakewell. (Ref. 4126)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £469

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A lovely stone-built annexe on the edge of the village of Rowsley, near Bakewell. En-suite, Smart TV, WiFi. Perfectly placed to explore Chatsworth, Bakewell, Matlock and Matlock Bath. Bakewell 3 miles. (Ref. 945481)

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

7 nights from £527

  • 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 £308