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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Homely, detached bungalow set in the town of Bolsover in Derbyshire. Conservatory. Smart TV. Luxury dog kennel. (Ref. 962748)

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

7 nights from $593

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

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

7 nights from $679

Last booked 2 days ago
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  • 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

7 nights from $1414

  • Sleeps7
  • Bedrooms3
  • PetsNo

    3.3

  • Sykes rating

This pleasant three-bedroom cottage rests in Darley Moor near Two Dales, Derbyshire. Dishwasher. Hot tub. Lakeside views. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129126)

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

7 nights from $725

  • 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 $1414

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful stone-built barn conversion resting on the outskirts of Matlock, Derbyshire. Open-plan. Views. Off-road parking. Matlock 2.1 miles; Bakewell 6.8 miles; Ashbourne 15.4 miles. (Ref. 1063970)

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

7 nights from $680

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A pleasant barn conversion situated near the village of Tansley in the Derbyshire Dales. Stunning views of Ogston Reservoir and countryside. Exposed beams. On working farm. Matlock 3 miles. (Ref. 969731)

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

7 nights from $454

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming, two-bedroom cottage resting in Bakewell, Derbyshire. Close to amenities. In National Park. Characterful. Off-road parking. Log effect gas fire. Chatsworth 4.5 miles; Matlock 8.4 miles; Buxton 11.9 miles. (Ref. 929026)

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

7 nights from $799

  • Sleeps3
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A charming period two bedroom end-terrace cottage with lots of character and excellent outdoor space in Matlock. Woodburner. WiFi. A very short walk to shops and pubs. Bakewell 8 miles. (Ref. 933358)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $508

  • Sleeps4
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • 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

7 nights from $618

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A fantastic five-bedroom detached house resting in Bakewell, Derbyshire. Pet-friendly. Woodburning stove. Off-road parking. Chatsworth 9.7 miles; Matlock 8.6 miles; Buxton 13.4 miles. (Ref. 921800)

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

7 nights from $2070

Last booked yesterday
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Belgrano is a charming detached house in Matlock Bath, Derbyshire, boasting a hot tub, pet-friendly policies and a barbecue with views of Matlock Bath. Matlock 2.9 miles; Bakewell 9.8 miles. (Ref. 1155098)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Fri 5th Sep to 8th Sep 2025

7 nights from $1236

  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • 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 $504

  • Sleeps6
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A stylish, end-terrace cottage set in the pretty village of Whitwell in Derbyshire. Loft conversion bedroom. En-suite. Centre of Whitwell. Worksop 5 miles. (Ref. 942650)

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

7 nights from $778

  • Sleeps6
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

An enchanting terrace cottage, set in the heart of Matlock, Derbyshire. Open plan kitchen and dining. Sitting room with wood burning stove. Garden to front and rear with patio and furniture. Matlock Bath 1 mile; Bakewell 8 miles. (Ref. 953252)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $552

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A quaint cottage nestled in the charming village of Crich in Derbyshire. Woodburning stove. Bike storage. Pet friendly. Matlock 6.4 miles; Bakewell 14.9 miles; Nottingham 18.3 miles. (Ref. 1038762)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $625

  • Sleeps11
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Barncroft is an outstanding detached bungalow situated in Tansley, Derbyshire boasting a double-sided log burner, hot tub, and elevated countryside views. Matlock 2 miles; Chesterfield 10.3 miles; Sutton-in-Ashfield 13.5 miles. (Ref. 1158073)

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

7 nights from $1843

  • 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

7 nights from $698

  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This impressive, five-bedroom property resides in Tansley near Matlock, Derbyshire. Off-road parking. Enclosed garden. Underfloor heating. Near a National Park. Matlock Bath 3.3 mile; Bakewell 10.2 miles. (Ref. 1057697)

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

7 nights from $1843

Last booked yesterday
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  • Sleeps4
  • Bedrooms1
  • PetsYes
  • Sykes rating

2 Rock Mill Holiday Apartments is a contemporary ground-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. 1165721)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom

7 nights from $645