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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 188 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Rose Cottage is a charming, stone-built cottage settled into the bustling town of Matlock, Derbyshire. Close to National Park. Near shop, pub, and river. Matlock Bath 1.8 miles; Peak District National Park 5 miles, Bakewell 8.7 miles. (Ref. 958573)

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


for 7 nights €842

  • Sleeps11
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • 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


for 7 nights €1568

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Peak Avenue Retreat is a charming holiday home, set over three floors, situated in the lovely village of Wingerworth near Chesterfield in Derbyshire. Matlock 9.4 miles; Chatsworth 10.2 miles; Bakewell 14.1 miles. (Ref. 1172926)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €480

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

33 Main Road is a detached, Grade II listed cottage resting in Higham, Derbyshire. Close to a lake. Close to a shop and pub. Near National Park. Matlock 6.6 miles; Peak District National Park 12.3 miles; Bakewell 15 miles. (Ref. 1147397)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €517

  • 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


for 7 nights €579

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • 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


for 7 nights €614

Last booked 7 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

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

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights €485

  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A fabulous, three-bedroom home resting in Matlock, Derbyshire. Countryside views. Near National Park. Close to amenities and attractions. Woodburning stove. Stylish. Matlock Bath 2.5 miles; Bakewell 9.3 miles. (Ref. 1118940)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • €102 off - Fri 28th Aug to 4th Sep 2026


for 7 nights €794

  • 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


for 7 nights €669

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    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


for 7 nights €458

  • Sleeps9
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • 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


for 7 nights €854

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Harebell Cottage is a delightful barn conversion resting in Curbar, Derbyshire. In National Park. Woodburning stove. Countryside views. Close to pub. Bakewell 6.1 miles; Sheffield 12.8 miles; Buxton 15.3 miles. (Ref. 1146083)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €691

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Converted chapel in the Derbyshire village of Handley. 19th century building. Original wooden beams. Open-plan living. Views of Ogston Reservoir. (Ref. 904605)

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


for 7 nights €484

  • Sleeps7
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

The Coach House, a stunning, pet-friendly house nestled in the village of Holloway in Derbyshire, featuring a woodburning stove, and off-road parking. Matlock Bath 4.1 miles; Matlock 4.4 miles; Peak District National Park 9 miles. (Ref. 1161872)

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


for 7 nights €940

  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Highview Stables is a pet-friendly cottage resting in the bustling market town of Chesterfield in Derbyshire with a woodburning stove and lovely views. Chatsworth 6.2 miles; Bakewell 8.9 miles; Matlock 9.9 miles. (Ref. 1169996)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights €608

Last booked 7 hours ago
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A remarkable stone-built holiday home resting in Teversal near Stanton Hill, Nottinghamshire. Enclosed garden. Character. Ground-floor living. Hot tub. Chesterfield 10.3 miles; Nottingham 19 miles; Peak District National Park 22.4 miles (Ref. 1080853)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Games room


for 7 nights €1368

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Mid-terrace cottage based in the market town of Dronfield in Derbyshire. Woodburning stove. Enclosed garden. Sheffield 7.2 miles. (Ref. 1035228)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €585

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Millers Retreat is a welcoming detached bungalow in Bolsover, Derbyshire, featuring a sun room and an enclosed rear garden. Chesterfield 6.5 miles; Sherwood Forest 11.7 miles; Sheffield 17 miles. (Ref. 1195936)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • 15% off - Fri 31st Jul to 4th Sep 2026


for 7 nights €460

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8

    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


for 7 nights €383

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A beautiful two-bedroom cottage resting in Grindleford, Derbyshire. Off-road parking.In the Peak District National Park. En-suite bedrooms. Smart TV. Eyam 3.1 miles; Baslow 3.6 miles; Bakewell 6.8 miles. (Ref. 1079242)

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


for 7 nights €677