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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 169 cottages

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  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.8

    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 £453

Last booked 2 days ago
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  • 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 £1095

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • 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 £467

Last booked yesterday
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  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Magnificent detached conversion with unusual layout near Baslow. Character accommodation. Breathtaking views, private hot tub and sauna. Near Chatsworth House. Bakewell 9 miles. (Ref. 2674)

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


for 7 nights £729

  • 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 £374

  • 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 £372

  • Sleeps4
  • 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 £425

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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 £380

  • 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 £1075

  • 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

  • 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 £496

  • 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 £413

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Character terraced property, originally part of stone barn just outside village of Barlow. With open plan living area and woodburner. Ideal base for walkers and cyclists. Barlow 1 mile. (Ref. 939317)

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


for 7 nights £353

  • 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 £407

  • 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 £454

Last booked 2 days ago
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  • 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 £572

  • 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 £364

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.3

    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 £719

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A lodge set in the owners garden in the market town of Dronfied, Derbyshire. Pet-friendly. Patio with furniture. Dishwasher. Chesterfield 6.3 miles; Sheffield 7.2 miles. (Ref. 1134158)

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


for 7 nights £307

  • 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
  • 5% off - Fri 12th Dec to 19th Dec 2025

  • 15% off - Sat 10th Jan to 17th Jan 2026


for 7 nights £1450

Last booked 2 days ago
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