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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 169 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    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 £582

  • 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

  • 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 £469

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • 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


for 7 nights £455

  • 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
  • 20% off - Wed 26th Nov to 6th Dec 2025


for 7 nights £443

  • 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 £518

  • Sleeps4
  • 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
  • 5% off - Tue 11th Nov to 20th Dec 2025


for 7 nights £412

  • 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 £541

Last booked 3 hours ago
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  • 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


for 7 nights £956

  • 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 £678

  • 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 £968

  • 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 £447

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.0

    Good

  • 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


for 7 nights £511

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.2

    Good

  • 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


for 7 nights £709

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.3

    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 £466

  • Sleeps7
  • Bedrooms2
  • PetsNo

    4.3

    Good

  • 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


for 7 nights £515

  • 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 £968

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.2

    Good

  • Sykes rating

11 The Hill is a wonderful, three-bedroom abode resting in Cromford, Derbyshire. Near Peak District National Park. Matlock Bath 1.2 mile; Matlock 2.6 miles; Bakewell 12.5 miles. (Ref. 1135369)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £440

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

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 £825

  • 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 £407