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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 188 cottages

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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A stylish, detached holiday home resting in Chesterfield, Derbyshire. Enclosed garden. Close to amenities. Family-friendly. Matlock 10 miles; Chatsworth 10 miles; Bakewell 13 miles. (Ref. 1087361)

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


for 7 nights From €722

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Lydgate Cottage is an original cottage sitting in the heart of Eyam, Derbyshire. Hot tub. Pet-friendly. Woodburning stove. Near amenities. In National Park. Tideswell 5.2 miles; Bakewell 6.8 miles. (Ref. 1066992)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher


for 7 nights From €860

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms4
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Havendale is a stunning single-storey holiday home in Chesterfield, Derbyshire, boasting accessible features, a woodburning stove, and an enclosed garden. Matlock 9.5 miles; Chatsworth 10.7 miles; Bakewell 13 miles. (Ref. 1167060)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From €1474

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

A beautiful, single-storey holiday home encapsulated by the countryside in Alton near Ashover, Derbyshire. Ground-floor living. Hot tub. Barbecue. Gym. Countryside views. Smart TVs. Ashover 1.9 miles, Matlock 5.1 miles, Chesterfield 5.6 miles (Ref. 1129371)

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


for 7 nights From €711

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Cherry Tree Farm is a wonderful detached abode set on the outskirts of Chesterfield, Derbyshire, enjoying a hot tub and close proximity to a National Park. Matlock 6 miles; Chatsworth 8.6 miles; Bakewell 9 miles. (Ref. 1165577)

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


for 7 nights From €2148

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A stunning barn conversion resting in Walton near Chesterfield, Derbyshire. Secluded. Near the Peak District National Park. Enclosed garden. Romantic. Matlock 7.2 miles; Bakewell 10.8 miles. (Ref. 1087716)

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


for 7 nights From €717

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

A Grade II listed property, resting on the outskirts of Clay Cross. Woodburning fire. WiFi. Hot tub. Set in a 100 acres of farmland. Chesterfield 5 miles. (Ref. 945165)

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


for 7 nights From €815

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Temperance Croft is a charming, single-storey holiday cottage resting in the quaint little village of Wadshelf in Derbyshire which is ideal for couples. Chatsworth 5.4 miles; Bakewell 8.3 miles; Matlock 9.1 miles. (Ref. 1155313)

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


for 7 nights From €428

Last booked 2 days ago
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  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A marvellous ground floor, detached cottage on the edge of Chesterfield in the Peak District. En-suite wet rooms. WiFi. Children's play area. Enclosed garden. Chatsworth House 8 miles. Chesterfield 2 miles. (Ref. 904429)

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


for 7 nights From €2158

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

A snug single-storey lodge situated in the quaint village of Wingerworth in Derbyshire. Pet friendly. Bike storage. WiFi. Chesterfield 2.8 miles; Matlock 8.4 miles; Ripley 11.6 miles. (Ref. 1073399)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From €484

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A superb two-bedroom, wooden-cladded lodge resting in Wingerworth, Derbyshire. Pet-friendly. Fantastic views. Off-road parking. Chesterfield 3.1 miles; Matlock 7.3 miles; Bakewell 11.9 miles. (Ref. 1076095)

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


for 7 nights From €633

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A charming lodge set in a lovely paddock, a few miles from the village of Ashover. Open-plan living. Dishwasher. Country setting. Chesterfield 5.1 miles; Matlock 5.8 miles. (Ref. 1123841)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From €593

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €499

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms2
  • Pet FriendlyNo

    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 From €680

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

An attractive dormer bungalow resting in Darley Dale, close to the Peak District National Park. Close to amenities. Off-road parking. Wheelchair friendly. Matlock 3.1 miles; Bakewell 5.5 miles; Ashbourne 15.4 miles. (Ref. 1077976)

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


for 7 nights From €660

  • Sleeps14
  • Bedrooms6
  • Pet FriendlyYes

    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)

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


for 7 nights From €2948

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    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)

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


for 7 nights From €826

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €529

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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 From €812