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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 176 cottages

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  • 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 £309

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This charming semi-detached cottage rests in Tansley, Derbyshire. Off-road parking. Woodburning stove. Pet-free. Garden with furniture. Matlock 1.7 miles. (Ref. 1061197)

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


for 7 nights £529

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Potters Cottage is a delightful, Victorian dwelling resting in Fulwood on the outskirts of Sheffield, South Yorkshire. Near National Park. Close to amenities. Stylish. Chesterfield 13.4 miles; Doncaster 24.6 miles. (Ref. 1140958)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • 10% off - Tue 29th Jul to 31st Oct 2025


for 7 nights £404

  • 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 £721

  • 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 £469

  • 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 £634

  • 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 £507

Last booked 3 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A converted church resting within Birchover, near Winster. Pet-friendly. WiFi. Pub within 0.2 miles. Matlock 6.5 miles. (Ref. 1005440)

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


for 7 nights £518

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A charming two-bedroom semi-detached house resting in Ashover, Derbyshire. Family-friendly. Smart TV. Near a river. Matlock 4.6 miles, Chesterfield 6.7 miles. (Ref. 1072527)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £415

Last booked 2 days ago
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  • 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 £338

  • 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 £716

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Beautiful stable conversion, all ground floor cottage with two bedrooms. Well-furnished. WiFi. Vineyard on-site. Sherwood Forest nearby. Warsop 1.2 miles. (Ref. 963639)

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


for 7 nights £396

Last booked yesterday
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  • Sleeps10
  • Bedrooms7
  • PetsYes
  • Sykes rating

Five Acres is a large, fun-filled holiday home on the outskirts of pretty market town of Chesterfield, Derbyshire, with a hot tub, sauna and games room. Matlock 9.8 miles; Chatsworth 10.1 miles; Bakewell 13.4 miles; Sheffield 14.8 miles. (Ref. 1166348)

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


for 7 nights £6960

  • 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 £913

Last booked yesterday
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  • 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 £385

  • 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 £481

  • 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 £401

  • 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 £521

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • 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


for 7 nights £922

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A stone-fronted, characterful cottage resting in Bakewell, Derbyshire. In National Park. Woodburning stove. Original features. Close to amenities. Enclosed courtyard. Chatsworth 4.8 miles; Matlock 9.7 miles; Buxton 12.6 miles. (Ref. 940794)

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


for 7 nights £625