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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

    4.7

    Sykes Rating

Beautiful stable conversion, all ground floor cottage with two bedrooms. Well-furnished. WiFi. Vineyard on-site. Sherwood Forest nearby. Warsop 1.2 miles. (Ref. 963639)

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

7 nights from £396

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A charming lodge set in a lovely paddock, a few miles from the village of Ashover. Open-plan living. Dishwasher. Country setting. Chesterfield 5.1 miles; Matlock 5.8 miles. (Ref. 1123841)

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

7 nights from £490

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A snug single-storey lodge situated in the quaint village of Wingerworth in Derbyshire. Pet friendly. Bike storage. WiFi. Chesterfield 2.8 miles; Matlock 8.4 miles; Ripley 11.6 miles. (Ref. 1073399)

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

7 nights from £455

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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 £408

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A wonderful ground-floor apartment in a Grade II listed building near Cuckney, Nottinghamshire. Ground-floor living. Dog-friendly. Original features. Family-friendly. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116402)

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

7 nights from £506

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1

    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

7 nights from £471

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

A pretty red brick terraced property, resting in the village of Creswell, Derbyshire. Spacious interior. Off-road parking. Smart TV. WiFi. Worksop 6.6 miles; Sheffield 14.9 miles; Matlock 19.9 miles. (Ref. 1021053)

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

7 nights from £374

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Sykes Rating

An end-terrace barn conversion near Barlow. With woodburner, open plan living area. Ideal touring base on edge of Peak District National Park. Barlow 1 mile. (Ref. 939316)

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

7 nights from £352

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A charming two-bedroom semi-detached house resting in Farley, Derbyshire Dales. Pet-friendly. Close to amenities. Hot tub. Matlock Bath 2.6 mile; Bakewell 7.9 miles. (Ref. 1084280)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Sat 3rd May to 2nd Aug 2025

7 nights from £668

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

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from £339

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

This semi-detached cottage can be found in the charming village of Two Dales in Matlock. Dogs welcome. En-suite bathroom. WiFi. Matlock 2.7 miles; Bakewell 6.4 miles. (Ref. 1038854)

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

7 nights from £399

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

The Chapel is a converted methodist chapel situated in Brackenfield near Stretton, Derbyshire. Character features. Open-plan living. Lawned garden. Alfreton 4.6 miles; Chesterfield 9.6 miles. (Ref. 1140286)

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

7 nights from £565

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

A lovely tastefully styled stone-built cottage, conveniently located in the pretty village of Stoney Middleton. Lovely views and secure bike storage. Bakewell 5.5 miles. (Ref. 940662)

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

7 nights from £416

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Sykes Rating

Whim Cottage, a traditional dwelling set in the village of Hathersage, Derbyshire. Woodburning stove. Good transport links. Enclosed garden. Pet-friendly. Curbar 6.3 miles; Castleton 6.5 miles. (Ref. 1135670)

  • Wi-fi
  • Off-road parking

7 nights from £420

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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. 996351)

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

7 nights from £347

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A listed two-bedroom chocolate box cottage resting in Bakewell, Derbyshire. Smart TV. Central location. Near a National Park. Chatsworth 4.7 miles; Matlock 8.3 miles; Buxton 12 miles. (Ref. 1087662)

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

7 nights from £608

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

Smithy Cottage, a well-appointed, two-bedroom cottage rests in Barlow near Chesterfield, Derbyshire. Near National Park. Contemporary. Close to amenities. Private driveway. Chatsworth 9.1 miles; Bakewell 10.6 miles; Matlock 12.8 miles. (Ref. 1132596)

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

7 nights from £424

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Courthouse Cottage is a characterful, former Magistrates Court with countryside views, near Peak District National Park, in Eckington, Derbyshire. Chesterfield 7.4 miles; Sheffield 8.4 miles; Doncaster 21.2 miles. (Ref. 1140580)

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

7 nights from £537

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from £516