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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 171 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    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

7 nights from €624

  • Sleeps12
  • Bedrooms5
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Lovely large, contemporary cottage with pretty views. En-suite bedroom, lovely garden. Perfect for Chatsworth House and Peak District. Bakewell 4 miles. (Ref. 17875)

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

7 nights from €920

Last booked yesterday
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  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint cottage nestled in the charming village of Crich in Derbyshire. Woodburning stove. Bike storage. Pet friendly. Matlock 6.4 miles; Bakewell 14.9 miles; Nottingham 18.3 miles. (Ref. 1038762)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €484

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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

7 nights from €479

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This superbly-renovated former barn is perched in Winster, Derbyshire. In a National Park. Off-road parking. Ground-floor living. EV charging. Open-plan. Bakewell 5.6 miles; Matlock 6.3 miles. (Ref. 1120845)

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

7 nights from €767

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A quaint, mid-terrace cottage settled in the village of Matlock, Derbyshire. Woodburner. Enclosed garden. Scenic location. Bakewell 4.7 miles; Matlock Bath 5 miles. (Ref. 1094150)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • €127 off - Sat 8th Nov to 15th Nov 2025

  • €128 off - Sat 22nd Nov to 29th Nov 2025

  • €127 off - Sat 13th Dec to 20th Dec 2025

  • €69 off - Sat 20th Dec to 27th Dec 2025

  • €170 off - Sat 3rd Jan to 10th Jan 2026

  • €115 off - Sat 10th Jan to 17th Jan 2026

7 nights from €518

  • Sleeps6
  • Bedrooms3
  • PetsNo

    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

7 nights from €548

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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 €688

Last booked 2 days ago
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A fantastic five-bedroom detached house resting in Bakewell, Derbyshire. Pet-friendly. Woodburning stove. Off-road parking. Chatsworth 9.7 miles; Matlock 8.6 miles; Buxton 13.4 miles. (Ref. 921800)

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

7 nights from €1677

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A well-presented, detached cottage nestled in the centre of Matlock, Derbyshire. Smart TV. South-facing terrace. Off-road parking. Bakewell 10.2 miles. (Ref. 1064755)

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

7 nights from €798

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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

7 nights from €770

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    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

7 nights from €585

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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

7 nights from €688

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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

7 nights from €648

Last booked 2 days ago
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  • Sleeps15
  • Bedrooms5
  • PetsYes

    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)

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

7 nights from €2153

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A lovely apartment in the centre of Eyam village in the Peak District National Park. Ideal for couples wishing to explore this historic area. Beautiful countryside with fabulous walks. Bakewell 7 miles. (Ref. 946764)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €350

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Matlock Maisonette is situated in Matlock in Derbyshire. Duplex apartment. Far-reaching views. Stunning terrace. Central location. Allocated parking. Bakewell 8.6 miles. Alfreton 9.2 miles. Sheffield 22.5 miles. (Ref. 1153088)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €733

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This studio property is set in the heart of Bakewell, Peak District National Park. Modern interior. Charming courtyard. Central location. (Ref. 989667)

  • Wi-fi

7 nights from €395

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • 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 €625

  • Sleeps12
  • Bedrooms5
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A spacious dwelling, resting on the outskirts of the town of Darley Dale. WiFi. Off-road parking. Pubs and shops within 1 mile. Bakewell 4 miles. (Ref. 17876)

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

7 nights from €920

Last booked yesterday
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