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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 190 cottages

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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Reading Room, a stunning reverse-level house in Grindleford, Derbyshire, set within Peak District National Park, offers a fire pit and allows pets. Hathersage 2.6 miles; Castleton 8.3 miles; Sheffield 11.2 miles. (Ref. 1196410)

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


for 7 nights From €762

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

    4.8

    Outstanding

  • Sykes rating

A lovely tastefully styled stone-built cottage, conveniently located in the pretty village of Stoney Middleton. Lovely views and secure bike storage. Bakewell 5.5 miles. (Ref. 940662)

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


for 7 nights From €441

  • 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 €677

  • 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 €430

Last booked 2 hours ago
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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 €659

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From €666

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Rock Mill Holiday Apartments is a stunning, third-floor apartment resting in Stoney Middleton, near Calver, Derbyshire. In Peak District National Park. Off-road parking. EV Charging. Calver 1 mile; Bakewell 5.7 miles; Sheffield 12.9 miles. (Ref. 1130694)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging


for 7 nights From €607

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7

    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 From €406

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

This charming terraced cottage sits in the Derbyshire town of Matlock. Over three floors. Pet-friendly. WiFi. Matlock Bath 1 mile. (Ref. 963763)

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


for 7 nights From €469

  • Sleeps3
  • Bedrooms1
  • Pet FriendlyNo

    4.6

    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
  • 5% off - Tue 14th Jul to 30th Sep 2026


for 7 nights From €449

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Bear Cottage, a pretty terraced cottage situated in the town of Cromford in Derbyshire, close to a shop and a pub, and the Peak District National Park. Matlock Bath 1.2 miles; Wirksworth 1.9 miles; Peak District National Park 7.2 miles. (Ref. 1100050)

  • Pets go free
  • Wi-fi
  • Baby-friendly


for 7 nights From €408

  • Sleeps3
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom


for 7 nights From €482