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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 176 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Yew Tree Cottage is a delightful, pet-friendly holiday cottage resting in the charming town of Matlock in Derbyshire with an enclosed decked balcony. Matlock Bath 1.9 miles; Bakewell 8.6 miles. (Ref. 1174717)

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


for 7 nights €523

  • Sleeps4
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • 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 €479

Last booked yesterday
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  • 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 €1070

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 €8059

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8

    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 €1026

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely one bedroom modern cottage with fantastic walks from the doorstep, on the edge of Rowsley village. Great views located between Bakewell and Matlock. Ideal romantic retreat. Bakewell 3 miles. (Ref. 941567)

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


for 7 nights €411

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A beautiful terraced miners cottage resting in Stanfree, Derbyshire. Electric woodburning stove. Close to Peak District National Park. Pet-friendly. Chesterfield 7 miles; Sheffield 15.4 miles. (Ref. 1112748)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €383

  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.9

    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 €498

  • 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 €1182

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • 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 €1145

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

    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
  • 5% off - Sat 27th Sep to 10th Oct 2025

  • 5% off - Thu 16th Oct to 24th Oct 2025


for 7 nights €504

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2

    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 €394

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Good

  • Sykes rating

A charming one-bedroom cottage resting in Ashover, Derbyshire. Close to Peak District National Park. Countryside views. Studio-layout. Private decking. Close to walking trails. Matlock 3.3 miles; Chesterfield 8.1 miles. (Ref. 1113330)

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


for 7 nights €400

  • 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 €392

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    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 €607

Last booked yesterday
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  • Sleeps7
  • Bedrooms4
  • PetsYes
  • Sykes rating

Blindwell House is a charming, family and pet-friendly cottage located in the village of Wensley in Derbyshire, boasting a woodburning stove and barbecue. Matlock 3.6 miles; Bakewell 7.2 miles; Ashbourne 13.7 miles; Derby 21.8 miles. (Ref. 1181996)

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


for 7 nights €739

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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 €392

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

62 Heritage Dr is a homely semi-detached house in Clowne, Derbyshire, EV charging, a travel cot and highchair available, and lovely views of the village. Chesterfield 8.8 miles; Sutton-in-Ashfield 12.1 miles; Sheffield 18.8 miles. (Ref. 1166380)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Washing machine
  • Baby-friendly


for 7 nights €511

  • 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 €382

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2

    Good

  • 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 €487