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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 167 cottages

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  • 14 Guests
  • 6 Bedrooms
  • Pets Yes

    Sykes Rating

Hallfield Hall is a stunning house situated in Shirland, Derbyshire, boasting a hot tub, bar, snooker table, games room, cinema room, and enclosed garden. Alfreton 2.4 miles; Matlock Bath 8.4 miles; Bakewell 15.1 miles; Derby 15.6 miles. (Ref. 1169570)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Games room

7 nights from €2972

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.5

    Sykes Rating

A charming semi-detached property resting in Baslow, Derbyshire. Garden. Off-road parking. Close to a pub. Calver 2.6 miles; Bakewell 4.6 miles; Sheffield 15.6 miles. (Ref. 1133131)

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

7 nights from €913

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.8

    Sykes Rating

The Bottling Shed, a wonderful holiday retreat lying in the scenic Peak District in Matlock, Derbyshire. Romantic retreat. Hot tub. Open-plan. Balcony. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1048671)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from €613

Last booked yesterday
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  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    4.8

    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

7 nights from €481

  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    4.9

    Sykes Rating

A delightful stone-built cottage nestled in Cromford, Derbyshire. Open-plan. Woodburning stove. Pet-friendly. Matlock 2.5 miles. (Ref. 1062326)

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

7 nights from €587

  • 6 Guests
  • 2 Bedrooms
  • Pets Yes

    4.5

    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

7 nights from €481

Last booked yesterday
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  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Toll Bar Cottage is a delightful, riverside dwelling resting in Baslow, Derbyshire. Riverside views. Near amenities. In National Park. Stylish. Bakewell 4.1 miles; Chatsworth 9.1 miles. (Ref. 964575)

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

7 nights from €1013

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    Sykes Rating

A well-appointed traditional cottage situated in the village of Higham, Derbyshire. Central location. Original features. Sun room. Ripley 5.5 miles. Matlock 8.9 miles. Bakewell 15.1 miles. (Ref. 1057608)

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

7 nights from €699

  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    4.9

    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)

  • Wi-fi
  • Baby-friendly

7 nights from €423

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    5.0

    Sykes Rating

A charming two-bedroom semi-detached house resting in Farley, Derbyshire Dales. Pet-friendly. Close to amenities. Hot tub. Matlock Bath 2.6 mile; Bakewell 7.9 miles. (Ref. 1084280)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Sat 3rd May to 2nd Aug 2025

7 nights from €853

Last booked yesterday
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  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

    Sykes Rating

Number 4 Westmoreland is a stylish ground-floor apartment with off-road parking, close to the Peak District in the village of Two Dales, Derbyshire. Matlock 2.5 miles; Bakewell 6.1 miles. (Ref. 1160185)

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

7 nights from €501

  • 6 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

A former carriage house in the market town of Dronfield. Stunning beams, en-suite, very comfortable accommodation.WiFi. Three miles from the Peak District National Park and within walking distance of every amenity. Sheffield 7 miles. (Ref. 931313)

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

7 nights from €667

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.7

    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

7 nights from €664

Last booked yesterday
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  • 9 Guests
  • 4 Bedrooms
  • Pets Yes

    4.8

    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
  • Dishwasher
  • Washing machine

7 nights from €871

  • 4 Guests
  • 1 Bedroom
  • Pets Yes

    4.9

    Sykes Rating

Cherry Tree Cottage is a stunning cottage near Chesterfield in Derbyshire. Romantic. Hot tub. Dog-friendly. Parking. Great views. Rural location. Matlock 6.5 miles; Bakewell 9.1 miles; Baslow 11 miles; Buxton 20.9 miles. (Ref. 1153986)

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

7 nights from €770

Last booked 2 days ago
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  • 3 Guests
  • 2 Bedrooms
  • Pets No

    5.0

    Sykes Rating

A charming period two bedroom end-terrace cottage with lots of character and excellent outdoor space in Matlock. Woodburner. WiFi. A very short walk to shops and pubs. Bakewell 8 miles. (Ref. 933358)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from €442

  • 3 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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

7 nights from €697

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A listed two-bedroom chocolate box cottage resting in Bakewell, Derbyshire. Smart TV. Central location. Near a National Park. Chatsworth 4.7 miles; Matlock 8.3 miles; Buxton 12 miles. (Ref. 1087662)

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

7 nights from €705

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Harebell Cottage is a delightful barn conversion resting in Curbar, Derbyshire. In National Park. Woodburning stove. Countryside views. Close to pub. Bakewell 6.1 miles; Sheffield 12.8 miles; Buxton 15.3 miles. (Ref. 1146083)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €756

  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    5.0

    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)

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

7 nights from €546