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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 169 cottages

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  • 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 €719

Last booked 2 days ago
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  • 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 €678

Last booked 2 days ago
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  • 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 €606

  • 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 €412

  • 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 €693

  • 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 €503

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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 €521

Last booked yesterday
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  • 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 €616

  • Sleeps12
  • Bedrooms5
  • PetsNo

    4.6

    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 €859

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming, two-bedroom cottage resting in Bakewell, Derbyshire. Close to amenities. In National Park. Characterful. Off-road parking. Log effect gas fire. Chatsworth 4.5 miles; Matlock 8.4 miles; Buxton 11.9 miles. (Ref. 929026)

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


for 7 nights €611

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Stone, mid-terrace cottage nestled a short stroll away from the pretty market town of Bakewell. Woodburner. Off-road parking. WiFi. Shop 0.6 miles, pub 0.5 miles. (Ref. 974373)

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


for 7 nights €644

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    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 €341

  • 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
  • 10% off - Fri 9th Jan to 16th Jan 2026

  • 5% off - Fri 23rd Jan to 30th Jan 2026

  • 5% off - Fri 30th Jan to 6th Feb 2026


for 7 nights €1332

  • 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 €441

  • 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 €1630

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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 €396

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    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 €538

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.7

    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 €775

  • 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 €537

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

46 Rock Mill is a stylish, third-floor apartment located in the stunning Hope Valley, in Derbyshire. Amenities on-site. In Peak District National Park. Tideswell 5.1 miles; Bakewell 6 miles. (Ref. 1148333)

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


for 7 nights €424