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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

    5.0

    Perfect

  • Sykes rating

Oakwood Lodge is a charming, detached holiday home in Tansley, Derbyshire. Countryside views. Near the Peak District National Park. Pet-friendly. Matlock 1.7 miles; Bakewell 10.2 miles; Derby 18.4 miles. (Ref. 1147569)

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


for 7 nights From €687

  • Sleeps11
  • Bedrooms4
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Barncroft is an outstanding detached bungalow situated in Tansley, Derbyshire boasting a double-sided log burner, hot tub, and elevated countryside views. Matlock 2 miles; Chesterfield 10.3 miles; Sutton-in-Ashfield 13.5 miles. (Ref. 1158073)

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


for 7 nights From €1614

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A pleasant barn conversion situated near the village of Tansley in the Derbyshire Dales. Stunning views of Ogston Reservoir and countryside. Exposed beams. On working farm. Matlock 3 miles. (Ref. 969731)

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


for 7 nights From €388

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • 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
  • 15% off - Sun 27th Sep to 5th Oct 2026


for 7 nights From €618

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Courthouse Cottage is a characterful, former Magistrates Court with countryside views, near Peak District National Park, in Eckington, Derbyshire. Chesterfield 7.4 miles; Sheffield 8.4 miles; Doncaster 21.2 miles. (Ref. 1140580)

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


for 7 nights From €571

  • Sleeps12
  • Bedrooms5
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

This impressive, five-bedroom property resides in Tansley near Matlock, Derbyshire. Off-road parking. Enclosed garden. Underfloor heating. Near a National Park. Matlock Bath 3.3 mile; Bakewell 10.2 miles. (Ref. 1203902)

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


for 7 nights From €1722

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

Mid-terrace cottage based in the market town of Dronfield in Derbyshire. Woodburning stove. Enclosed garden. Sheffield 7.2 miles. (Ref. 1035228)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €566

  • Sleeps14
  • Bedrooms5
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Highgate House is a charming holiday home resting in Holmesfield near Dronfield, Derbyshire, with a hot tub, pool table, and enclosed garden. Chesterfield 7.7 miles; Sheffield 9.6 miles. (Ref. 1179440)

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


for 7 nights From €2454

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A beautiful two-bedroom cottage resting in Grindleford, Derbyshire. Off-road parking.In the Peak District National Park. En-suite bedrooms. Smart TV. Eyam 3.1 miles; Baslow 3.6 miles; Bakewell 6.8 miles. (Ref. 1079242)

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


for 7 nights From €750

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

33 Main Road is a detached, Grade II listed cottage resting in Higham, Derbyshire. Close to a lake. Close to a shop and pub. Near National Park. Matlock 6.6 miles; Peak District National Park 12.3 miles; Bakewell 15 miles. (Ref. 1147397)

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


for 7 nights From €518

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

The Bungalow is a delightful detached house in Matlock, Derbyshire, boasting a hot tub, town views, enclosed garden and spacious open-plan living. Matlock Bath 1.1 miles; Bakewell 8.5 miles. (Ref. 1194384)

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


for 7 nights From €1279

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

A remarkable stone-built holiday home resting in Teversal near Stanton Hill, Nottinghamshire. Enclosed garden. Character. Ground-floor living. Hot tub. Chesterfield 10.3 miles; Nottingham 19 miles; Peak District National Park 22.4 miles (Ref. 1080853)

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


for 7 nights From €1325

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Wayside Cottage is a delightful rural retreat near Matlock in Derbyshire with communal gardens, beautiful views and well-presented interior. Bakewell 9.7 miles, Sheffield 21.7 miles. (Ref. 1198441)

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


for 7 nights From €386

Last booked 3 days ago
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

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

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights From €474

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • 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)

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


for 7 nights From €810

Last booked yesterday
See more details
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Peak Avenue Retreat is a charming holiday home, set over three floors, situated in the lovely village of Wingerworth near Chesterfield in Derbyshire. Matlock 9.4 miles; Chatsworth 10.2 miles; Bakewell 14.1 miles. (Ref. 1172926)

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


for 7 nights From €533

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Laneside Barn featuring a Freestanding Bath, is a romantic barn conversion nestled in the heart of the pretty Peak District National Park in Calver, a quaint village in Derbyshire. Baslow 1.6 miles; Eyam 2.1 miles; Bakewell 4.7 miles. (Ref. 1207012)

  • Wi-fi


for 7 nights From €441

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

This semi-detached cottage can be found in the charming village of Two Dales in Matlock. Dogs welcome. En-suite bathroom. WiFi. Matlock 2.7 miles; Bakewell 6.4 miles. (Ref. 1038854)

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


for 7 nights From €505

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Coach House, a stunning, pet-friendly house nestled in the village of Holloway in Derbyshire, featuring a woodburning stove, and off-road parking. Matlock Bath 4.1 miles; Matlock 4.4 miles; Peak District National Park 9 miles. (Ref. 1161872)

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


for 7 nights From €955