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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

2 Rock Mill Holiday Apartments is a contemporary ground-floor apartment in the heart of the Peak District National Park, in Stoney Middleton, Derbyshire. Eyam 0.8 miles; Baslow 2.8 miles; Bakewell 5.9 miles. (Ref. 1165721)

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


for 7 nights $605

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1

    Good

  • Sykes rating

An end-terrace barn conversion near Barlow. With woodburner, open plan living area. Ideal touring base on edge of Peak District National Park. Barlow 1 mile. (Ref. 939316)

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


for 7 nights $502

  • Sleeps3
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

28 Rock Mill Holiday Apartments is a contemporary second-floor apartment in the heart of the Peak District National Park, in Stoney Middleton, Derbyshire. Eyam 0.8 miles; Baslow 2.8 miles; Bakewell 5.9 miles. (Ref. 1165722)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging


for 7 nights $567

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A truly breath-taking converted water tower on the outskirts of Bolsover, Derbyshire. Woodburning stove. Stylish and contemporary. Romantic. Off-road parking. 6 acres of land. Chesterfield 7.7 miles; Sherwood Forest 9.7 miles; Sheffield 16.6 miles. (Ref. 1116427)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $1418

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A charming duplex apartment set in a Grade II listed building in Cuckney, Nottinghamshire. Character features. Off-road parking. En-suite bathrooms. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116401)

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


for 7 nights $1153

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4

    Good

  • Sykes rating

Oxcroft View is a family-friendly, semi-detached home situated in Oxcroft near Clowne in Derbyshire, offering an external games room and off-road parking. Chesterfield 8.2 miles; Sheffield 16.6 miles. (Ref. 1174188)

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


for 7 nights $623

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

A charming mews cottage resting in Stoney Middleton, Derbyshire. Barbecue. En-suite bedrooms. In the Peak District National Park. Eyam 1.2 miles; Bakewell 5.6 miles; Chapel-en-le-Frith 12.1 miles. (Ref. 1070240)

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


for 7 nights $1434

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A charming, stone-built cottage set in the Derbyshire village of Cromford. Mid-terrace. Centre of Cromford. Three storey. Matlock Bath 1 mile; Matlock 3 miles; Bakewell 10 miles. (Ref. 935996)

  • Wi-fi
  • Off-road parking


for 7 nights $501

  • Sleeps14
  • Bedrooms7
  • PetsNo

    4.1

    Good

  • Sykes rating

A Grade I listed property in a tranquil and historic Derbyshire setting in the village of Cromford. Near Peak District National Park. Off-road parking. Large garden. Matlock Bath 1.2 miles; Matlock 2.3 miles; Bakewell 10.8 miles. (Ref. 1050404)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 15% off - Sat 10th Jan to 17th Jan 2026


for 7 nights $2078

  • 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 $662

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

A pretty red brick terraced property, resting in the village of Creswell, Derbyshire. Spacious interior. Off-road parking. Smart TV. WiFi. Worksop 6.6 miles; Sheffield 14.9 miles; Matlock 19.9 miles. (Ref. 1021053)

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


for 7 nights $543

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A charming three-bedroom detached cottage resting in Matlock, Derbyshire. Child-friendly. Enclosed garden. Castle views. Matlock Bath 1.6 miles; Bakewell 8.8 miles. (Ref. 1068675)

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


for 7 nights $626

  • 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 $835

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A semi-detached property nestled in the market town of Bakewell, Derbyshire. Smart TV. Close to amenities. In National Park. Electric fire. Matlock 8.5 miles; Chatsworth 9.2 miles. (Ref. 1104863)

  • Wi-fi
  • Washing machine


for 7 nights $691

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Churchside House is a charming, three-bedroom holiday cottage resting in Matlock, Derbyshire. Close to amenities. Near a National Park. Electric fire. Matlock Bath 2.8 mile; Bakewell 8.9 miles. (Ref. 1105058)

  • Dishwasher
  • Washing machine


for 7 nights $607

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Tourist Board rating

Pineapple Cottage is a charming mid-terrace retreat resting in Bakewell, Derbyshire, with an electric fire and direct access to the Monsal Trail. Chatsworth 3.3 miles; Matlock 9.2 miles; Buxton 13 miles. (Ref. 1189992)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $543

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.2

    Good

  • Sykes rating

Roseville is a charming, 18th-century property resting in the riverside town of Cromford, Derbyshire, Close to a National Park, and with a hot tub. Matlock 3 miles; Peak District National Park 7.3 miles; Bakewell 11 miles. (Ref. 1155096)

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


for 7 nights $982

  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

8 Inns Lane is a delightful, three-bedroom holiday home resting in South Wingfield, Derbyshire. Near a National Park. Close to pub. Off-road parking. Pet-free. Matlock 6.4 miles. (Ref. 1142655)

  • Wi-fi
  • Washing machine


for 7 nights $486

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Whim Cottage, a traditional dwelling set in the village of Hathersage, Derbyshire. Woodburning stove. Good transport links. Enclosed garden. Pet-friendly. Curbar 6.3 miles; Castleton 6.5 miles. (Ref. 1135670)

  • Wi-fi
  • Off-road parking


for 7 nights $606


for 7 nights $563