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Holiday Cottages Chesterfield

Your Chesterfield, Derbyshire search returned 185 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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


for 7 nights £537

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Wigley Farm House Cottage is a fabulous pet-friendly bungalow near Chesterfield, Derbyshire, boasting a woodburning stove, a hot tub and countryside views. Chatsworth 6.7 miles; Bakewell 8.3 miles; Matlock 9.9 miles. (Ref. 1182208)

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


for 7 nights £714

  • 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 £725

Last booked 2 days ago
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  • 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 £332

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Causeway Hideaway is a delightful, single-storey annexe resting in Dore, South Yorkshire. Romantic. Close to amenities. Stylish. Near National Park. Sheffield 5.4 miles; Chesterfield 11.7 miles. (Ref. 1133830)

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


for 7 nights £442

  • 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 £449

Last booked 2 days ago
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  • 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 £503

Last booked 2 days ago
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  • 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 £427

  • Sleeps14
  • Bedrooms6
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Hallfield Hall is a stunning house situated in Shirland, Derbyshire, boasting a hot tub, bar, snooker table, games room, cinema room, and enclosed garden. Alfreton 2.4 miles; Matlock Bath 8.4 miles; Bakewell 15.1 miles; Derby 15.6 miles. (Ref. 1169570)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Baby-friendly
  • Games room


for 7 nights £2520

  • 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 £572

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A well-appointed traditional cottage situated in the village of Higham, Derbyshire. Central location. Original features. Sun room. Ripley 5.5 miles. Matlock 8.9 miles. Bakewell 15.1 miles. (Ref. 1057608)

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


for 7 nights £534

Last booked 4 hours ago
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  • 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 £398

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A charming single-storey, stone-fronted cottage, resting in Stone Edge, Derbyshire. Close to Peak District National Park. Woodburning stove. Countryside views. Open-plan. EV charging point. Ashover 3.6 miles; Chesterfield 4.9 miles; Matlock 6 miles. (Ref. 1099455)

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


for 7 nights £775

Last booked 6 hours ago
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  • 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 £825

  • Sleeps16
  • Bedrooms8
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This beautiful Victorian townhouse rests in Matlock, Derbyshire. Set over four floors. En-suite in all bedrooms. Games room. Perfect for family gatherings. Matlock Bath 1.6 miles; Bakewell 8.5 miles; Buxton 20.2 miles. (Ref. 1018117)

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


for 7 nights £1622

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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


for 7 nights £414

  • 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 £592

Last booked 6 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 £421

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely, detached house in the centre of Barrow Hill. Three bedrooms, WiFi and pet-friendly. Chesterfield 5.5 miles. (Ref. 933885)

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


for 7 nights £407

Last booked 2 days ago
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  • 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 £1363