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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 171 cottages

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  • Sleeps18
  • Bedrooms9
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Sensational, detached conversion of the Arkwright’s Grade II listed former corn mill in Cromford. En-suite facilities. Three kitchens and sitting rooms. Feature beams and stonework. Lawned garden with furniture, mill pond and waterfall. Matlock 3 miles. (Ref. 17888)

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


for 7 nights €2541

Last booked 2 hours ago
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  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A detached farmhouse located in the village of Hathersage in Hope Valley. Woodburners. Pet-friendly. Four bedrooms. Castleton 5 miles. Curbar 5 miles. (Ref. 952361)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • €138 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights €1452

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Superb first floor apartment in Matlock. Individually styled, open plan accommodation, close to amenities. National Park within easy reach. Bakewell 8 miles. (Ref. 2401)

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


for 7 nights €402

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A splendid one-bedroom single-storey cottage settled in Alfreton near Oakerthorpe, Derbyshire. Pet and child friendly. Hot tub. Off-road parking. Crich 2.8 miles; Matlock 8.3 miles. (Ref. 991273)

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


for 7 nights €472

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful log cabin based just outside of the village of Rowsley in Derbyshire. Open plan modern accomodation. En-suite. Pet friendly. Rowsley 5 miles. Matlock 5 miles. (Ref. 936154)

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


for 7 nights €548

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Timeless cosy cottage with off street parking within a short stroll of the lovely bustling village of Bakewell. Accommodating up to six guests and a cosy woodburning stove makes Corner Cottage the perfect choice. Chatsworth 4 miles. (Ref. 926401)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €729

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

9 White Edge Close is a pleasing, semi-detached home located in Chesterfield in Derbyshire, enjoying close proximity to the Peak District National Park. Matlock 10.2 miles; Chatsworth 9.4 miles; Bakewell 12.7 miles. (Ref. 1168890)

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


for 7 nights €550

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    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 €655

Last booked 7 hours ago
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  • Sleeps6
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

An enchanting terrace cottage, set in the heart of Matlock, Derbyshire. Open plan kitchen and dining. Sitting room with wood burning stove. Garden to front and rear with patio and furniture. Matlock Bath 1 mile; Bakewell 8 miles. (Ref. 953252)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights €427

  • 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 €1005

  • 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


for 7 nights €489

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Superb semi-detached stable conversion in small village of Ashover. En-suite shower room, off road parking. Beautifully renovated to highest of standards. Excellent base for walking, cycling and exploring the Peak District. Matlock 5 miles. (Ref. 927577)

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


for 7 nights €703

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms5
  • PetsNo
  • Sykes rating

Old Manor House is a charming and traditonal holiday home located in the village of Cutthorpe in Derbyshire with two woodburning stoves and large gardens. Chatsworth 9 miles; Bakewell 10.5 miles; Matlock 11.9 miles. (Ref. 1169415)

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


for 7 nights €1656

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A lovely stone-built annexe on the edge of the village of Rowsley, near Bakewell. En-suite, Smart TV, WiFi. Perfectly placed to explore Chatsworth, Bakewell, Matlock and Matlock Bath. Bakewell 3 miles. (Ref. 945481)

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


for 7 nights €607

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This characterful terraced property resides in Chesterfield, Derbyshire. Enclosed garden. Conservatory. Smart TV. Near a National Park. Matlock 10.6 miles; Chatsworth 10 miles; Bakewell 14.1 miles. (Ref. 1122937)

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


for 7 nights €739

  • 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 €824

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Wigley Farm House Cottage is a fabulous pet-friendly bungalow near Chesterfield, Derbyshire, boasting a woodburning stove, a hot tub and countryside views. Chatsworth 6.7 miles; Bakewell 8.3 miles; Matlock 9.9 miles. (Ref. 1182208)

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


for 7 nights €745

Last booked 5 hours ago
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  • 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 €732

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    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 €469

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    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 €598