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Holiday Cottages Chesterfield

Your Chesterfield, Derbyshire search returned 189 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 FriendlyNo

    5.0

    Perfect

  • Sykes rating

An attractive dormer bungalow resting in Darley Dale, close to the Peak District National Park. Close to amenities. Off-road parking. Wheelchair friendly. Matlock 3.1 miles; Bakewell 5.5 miles; Ashbourne 15.4 miles. (Ref. 1077976)

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


for 7 nights From £574

  • 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 £427

  • Sleeps4
  • Bedrooms1
  • Pet FriendlyYes

    4.8

    Outstanding

  • 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)

  • Pets go free
  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Thu 9th Jul to 31st Aug 2026


for 7 nights From £640

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Naseby Houseis a welcoming abode in Morton near Alfreton, Derbyshire, with pet-friendly accommodation and close by National Park. Alfreton 4.6 miles; Peak District National Park 12.4 miles. (Ref. 1199153)

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


for 7 nights From £516

  • 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 £484

Last booked 8 hours ago
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  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A spacious, detached property resting in Holmesfield, Derbyshire. Dishwasher. Ample off-road parking. Woodburning stove. Chesterfield 6.7 miles; Sheffield 8.4 miles. (Ref. 1103519)

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


for 7 nights From £1165

Last booked 8 hours ago
See more details
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Causeway Hideaway is a delightful, single-storey annexe resting in Dore, South Yorkshire. Romantic. Close to amenities. Stylish. Near National Park. Sheffield 5.4 miles; Chesterfield 11.7 miles. (Ref. 1133830)

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


for 7 nights From £409

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Little Mill is a charming, pet-friendly, first-floor apartment in Ashover, Derbyshire, alongside the River Amber, boasting a well-equipped space. Matlock 4.4 miles. (Ref. 8739)

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


for 7 nights From £367

Last booked yesterday
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  • Sleeps14
  • Bedrooms6
  • Pet FriendlyYes

    5.0

    Perfect

  • 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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Baby-friendly
  • Games room


for 7 nights From £2520

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A superb two-bedroom bungalow resting on the outskirts of Dronfield, near Chesterfield, Derbyshire. Family-friendly. Large partially enclosed garden. Dog friendly. Peak District. Bakewell 12.8 miles; Matlock 13.2 miles. (Ref. 1084691)

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


for 7 nights From £554

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Converted chapel in the Derbyshire village of Handley. 19th century building. Original wooden beams. Open-plan living. Views of Ogston Reservoir. (Ref. 904605)

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


for 7 nights From £420

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • 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
  • £134 off - Sat 8th Aug to 15th Aug 2026


for 7 nights From £709

  • 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
  • 10% off - Fri 24th Jul to 7th Aug 2026

  • 7.5% off - Fri 7th Aug to 28th Aug 2026


for 7 nights From £421

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Rose Cottage is a charming, stone-built cottage settled into the bustling town of Matlock, Derbyshire. Close to National Park. Near shop, pub, and river. Matlock Bath 1.8 miles; Peak District National Park 5 miles, Bakewell 8.7 miles. (Ref. 958573)

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


for 7 nights From £695

  • 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 £452

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A delightful stone-built barn conversion resting on the outskirts of Matlock, Derbyshire. Open-plan. Views. Off-road parking. Matlock 2.1 miles; Bakewell 6.8 miles; Ashbourne 15.4 miles. (Ref. 1063970)

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


for 7 nights From £434

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From £648