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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 176 cottages

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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A contemporary first-floor apartment in Clay Cross, Derbyshire. Pet-friendly. Countryside views. Close to amenities. Smart TV. Chesterfield 5.1 miles; Matlock 7.8 miles; Peak District National Park 9.6 miles. (Ref. 1065378)

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


for 7 nights $742

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful, terraced cottage in the heart of Bakewell, Derbyshire. Within Peak District National Park. Romantic. Permit parking. Enclosed patio. Pet-friendly. Chatsworth 9.7 miles; Buxton 12.4 miles; Sheffield 17.3 miles. (Ref. 1134730)

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


for 7 nights $622

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A wonderful ground-floor apartment in a Grade II listed building near Cuckney, Nottinghamshire. Ground-floor living. Dog-friendly. Original features. Family-friendly. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116402)

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


for 7 nights $754

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This lovely little stone cottage sits in the Derbyshire village of Cromford. Near Peak District National Park. WiFi. Matlock 3 miles. (Ref. 981522)

  • Wi-fi
  • Off-road parking


for 7 nights $410

  • Sleeps12
  • Bedrooms5
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Lovely large, contemporary cottage with pretty views. En-suite bedroom, lovely garden. Perfect for Chatsworth House and Peak District. Bakewell 4 miles. (Ref. 17875)

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


for 7 nights $1059

Last booked 3 hours ago
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  • 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


for 7 nights $470

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This studio property is set in the heart of Bakewell, Peak District National Park. Modern interior. Charming courtyard. Central location. (Ref. 989667)

  • Wi-fi


for 7 nights $482

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Alfreton Cottage is a fabulous, dog-friendly holiday cottage in Newton near Alfreton, Derbyshire near the Peak District. South Normanton 1.6 miles; Oakerthorpe 5.2 miles; Kirkby-in-Ashfield 5.3 miles (Ref. 1162722)

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


for 7 nights $511

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Old Apothecary is a Grade II listed duplex apartment in Matlock Bath, near Matlock, Derbyshire. Close to a pub. Historic property. Riverside views. Matlock 1.6 miles; Peak District National Park 5.9 miles; Bakewell 9.6 miles. (Ref. 1139646)

  • Wi-fi
  • Dishwasher


for 7 nights $672

Last booked 6 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    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 $540

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A characterful terrace cottage set in the idyllic village of Darley Bridge, on the edge of the Peak District National Park. Countryside retreat. Original features. Pet-friendly. Matlock 2.9 miles; Bakewell 6.1 miles; Buxton 18.4 miles. (Ref. 1058614)

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


for 7 nights $515

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

A charming, stone cottage situated in the village of Whatstandwell, Derbyshire. Woodburning stove. Pet-friendly. Ample off-road parking. Matlock 5.9 miles. (Ref. 1136426)

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


for 7 nights $637

  • Sleeps15
  • Bedrooms5
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Wonderful Grade ll listed former coaching inn on edge of Peak National Park, close to village of Holmesfield. First class accommodation, outstanding views. Games room, hot tub. Bakewell 10 miles. (Ref. 2564)

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


for 7 nights $2799

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Cosy stone-built barn conversion on the owners' working livestock farm, two miles from Matlock. Large garden, pet-friendly. Walks from the doorstep. Opposite Matlock Golf Club. Bakewell 10 miles. (Ref. 929053)

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


for 7 nights $449

  • Sleeps12
  • Bedrooms5
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A spacious dwelling, resting on the outskirts of the town of Darley Dale. WiFi. Off-road parking. Pubs and shops within 1 mile. Bakewell 4 miles. (Ref. 17876)

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


for 7 nights $955

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Lovely detached bungalow close to centre of the Derbyshire market town of Matlock. Edge of Peak District National Park. Bakewell 8 miles. (Ref. 5689)

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


for 7 nights $690

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.1

    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
  • 5% off - Sun 2nd Nov to 9th Nov 2025


for 7 nights $1198

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

This charming terraced cottage sits in the Derbyshire town of Matlock. Over three floors. Pet-friendly. WiFi. Matlock Bath 1 mile. (Ref. 963763)

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


for 7 nights $532

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

This charming, four-bedroom home rests in Sheffield, South Yorkshire. Near a National Park. Smart TV. Off-road parking. Enclosed garden. Chesterfield 9.6 miles; Doncaster 21.9 miles. (Ref. 1134637)

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


for 7 nights $826

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Outstanding, semi-detached stone- built cottage. In the picturesque village of Baslow. Luxuriously appointed throughout. A lovely, romantic retreat for couples. Chatsworth 1 mile. (Ref. 939173)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $948