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Holiday Cottages Chesterfield

Your Chesterfield, Derbyshire search returned 195 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A converted church resting within Birchover, near Winster. Pet-friendly. WiFi. Pub within 0.2 miles. Matlock 6.5 miles. (Ref. 1005440)

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


for 7 nights From £516

  • Sleeps15
  • Bedrooms5
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Wonderful Grade ll listed former coaching inn on edge of Peak National Park, close to village of Holmesfield. First class accommodation, outstanding views. Games room, hot tub. Bakewell 10 miles. (Ref. 2564)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £2121

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £360

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

This charming detached house rests within the Peak District National Park in Wensley near Winster, Derbyshire. Enclosed garden. WiFi. Smart TV. Gas Fire. Winster 1.5 miles; Matlock 3.7 miles; Bakewell 7.2 miles. (Ref. 1077706)

  • Wi-fi
  • Hot Tub
  • Dishwasher


for 7 nights From £502

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.1

    Good

  • Sykes rating

2 Knoll Mount is a beautiful stone-built cottage in Tansley, Derbyshire, with original features, a woodburning stove,and access to the Peak District. Matlock 2.2 miles; Peak District National Park 6.8 miles; Bakewell 10.4 miles. (Ref. 1197451)

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


for 7 nights From £406

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Lumford Mill Cottage is an idyllic cottage settled into the bustling riverside village of Bakewell, Derbyshire, in the Peak District National Park. Matlock 9 miles; Buxton 11.9 miles; Edale 17.8 miles. (Ref. 1184351)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £564

Last booked 4 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From £336

  • Sleeps9
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From £1225

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    Outstanding

  • Tourist Board rating

Meadow View Cottage is a charming retreat in Whatstandwell near Crich, Derbyshire, with a woodburning stove and enclosed garden. Matlock 6.3 miles. (Ref. 1191047)

  • Wi-fi
  • Off-road parking


for 7 nights From £378

  • Sleeps5
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Baytree House is a well‑presented end‑terrace holiday home situated in Sheffield, South Yorkshire, featuring open‑plan living, enclosed patio and off‑road parking. Chesterfield 10.7 miles; Doncaster 27.3 miles. (Ref. 1203117)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £500

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Alexandra Retreat, a charming house resting in Sutton-In-Ashfield, near the Peak District National Park, boasts gas central heating and an enclosed garden. Mansfield 3.1 miles; Chesterfield 11.4 miles. (Ref. 1189857)

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


for 7 nights From £451

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £589

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From £314

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From £490

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

Deeley House is a charming, Georgian-period home set on the edge of the pretty Peak District National Park in Darley Dale, Derbyshire, welcoming pets. Matlock 3.7 miles; Bakewell 4.7 miles; Ashbourne 15.8 miles. (Ref. 1167997)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £924

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    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)

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


for 7 nights From £573

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Holt Hall - Ground Floor Apartment is a welcoming apartment in the bustling town of Matlock, Derbyshire, with close by shops, pubs, and walks. Matlock Bath 1.4 miles; Peak District National Park 4.8 miles; Bakewell 8.4 miles. (Ref. 1161643)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly


for 7 nights From £348

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From £627

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.4

    Good

  • 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 From £336