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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 173 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • 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


for 7 nights £407

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A charming, stone-built cottage set in the Derbyshire village of Cromford. Mid-terrace. Centre of Cromford. Three storey. Matlock Bath 1 mile; Matlock 3 miles; Bakewell 10 miles. (Ref. 935996)

  • Wi-fi
  • Off-road parking


for 7 nights £374

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Oxcroft View is a family-friendly, semi-detached home situated in Oxcroft near Clowne in Derbyshire, offering an external games room and off-road parking. Chesterfield 8.2 miles; Sheffield 16.6 miles. (Ref. 1174188)

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


for 7 nights £466

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

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


for 7 nights £579

  • Sleeps3
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

28 Rock Mill Holiday Apartments is a contemporary second-floor apartment in the heart of the Peak District National Park, in Stoney Middleton, Derbyshire. Eyam 0.8 miles; Baslow 2.8 miles; Bakewell 5.9 miles. (Ref. 1165722)

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


for 7 nights £413

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

A charming, stone cottage situated in the village of Whatstandwell, Derbyshire. Woodburning stove. Pet-friendly. Ample off-road parking. Matlock 5.9 miles. (Ref. 1136426)

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


for 7 nights £503

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stone-fronted, characterful cottage resting in Bakewell, Derbyshire. In National Park. Woodburning stove. Original features. Close to amenities. Enclosed courtyard. Chatsworth 4.8 miles; Matlock 9.7 miles; Buxton 12.6 miles. (Ref. 940794)

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


for 7 nights £627

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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


for 7 nights £420

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • 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


for 7 nights £526

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1

    Good

  • 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


for 7 nights £350

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

A charming mews cottage resting in Stoney Middleton, Derbyshire. Barbecue. En-suite bedrooms. In the Peak District National Park. Eyam 1.2 miles; Bakewell 5.6 miles; Chapel-en-le-Frith 12.1 miles. (Ref. 1070240)

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


for 7 nights £987

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A charming three-bedroom detached cottage resting in Matlock, Derbyshire. Child-friendly. Enclosed garden. Castle views. Matlock Bath 1.6 miles; Bakewell 8.8 miles. (Ref. 1068675)

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


for 7 nights £456

Last booked 7 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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


for 7 nights £339

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

Deeley House is a charming, Georgian-period home set on the edge of the pretty Peak District National Park in Darley Dale, Derbyshire, welcoming pets. Matlock 3.7 miles; Bakewell 4.7 miles; Ashbourne 15.8 miles. (Ref. 1167997)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 7.5% off - Thu 1st Jan to 31st Jan 2026


for 7 nights £958

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • 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


for 7 nights £666

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A semi-detached property nestled in the market town of Bakewell, Derbyshire. Smart TV. Close to amenities. In National Park. Electric fire. Matlock 8.5 miles; Chatsworth 9.2 miles. (Ref. 1104863)

  • Wi-fi
  • Washing machine


for 7 nights £497

Last booked 8 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    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


for 7 nights £347

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • 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


for 7 nights £552

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.0

    Good

  • 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


for 7 nights £687

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A lodge set in the owners garden in the market town of Dronfied, Derbyshire. Pet-friendly. Patio with furniture. Dishwasher. Chesterfield 6.3 miles; Sheffield 7.2 miles. (Ref. 1134158)

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


for 7 nights £322