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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 171 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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


for 7 nights €562

Last booked 4 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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 €446

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    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 €594

  • Sleeps3
  • Bedrooms2
  • PetsNo

    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 €539

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Converted chapel. One en-suite bedroom. Private patio with furniture. Woodburning stove. Crich 3.3 miles. Matlock 4 miles. (Ref. 924332)

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


for 7 nights €406

Last booked yesterday
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  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Ty Gambo is a holiday house resting in the village of Oker in Derbyshire. Hot tub. Woodburning stove. Smart TV. Off-road parking. In National Park. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1142883)

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


for 7 nights €1567

  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • 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. 1057697)

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


for 7 nights €1718

  • Sleeps8
  • Bedrooms4
  • PetsYes

    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)

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


for 7 nights €1386

  • Sleeps10
  • Bedrooms5
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Cherry Tree Farm is a wonderful detached abode set on the outskirts of Chesterfield, Derbyshire, enjoying a hot tub and close proximity to a National Park. Matlock 6 miles; Chatsworth 8.6 miles; Bakewell 9 miles. (Ref. 1165577)

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


for 7 nights €1828

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 €473

  • 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


for 7 nights €624

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €517

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Beautiful barn conversion in a rural location, near the village of Ashover on edge of the Peak District. WiFi. Countryside views across valley. Off-road parking. Electric stove. Matlock 5 miles. (Ref. 996351)

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


for 7 nights €365

Last booked yesterday
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  • Sleeps16
  • Bedrooms8
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This beautiful Victorian townhouse rests in Matlock, Derbyshire. Set over four floors. En-suite in all bedrooms. Games room. Perfect for family gatherings. Matlock Bath 1.6 miles; Bakewell 8.5 miles; Buxton 20.2 miles. (Ref. 1018117)

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


for 7 nights €1910

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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


for 7 nights €701

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A terraced cottage located in the village of Birchover in the Peak District. Wood burner. Paved garden with furniture. Quiet location. Winster 1.3 miles; Bakewell 5.4 miles; Matlock 5.5 miles. (Ref. 953759)

  • Wi-fi
  • Washing machine


for 7 nights €496

Last booked 3 days ago
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  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Highview Stables is a pet-friendly cottage resting in the bustling market town of Chesterfield in Derbyshire with a woodburning stove and lovely views. Chatsworth 6.2 miles; Bakewell 8.9 miles; Matlock 9.9 miles. (Ref. 1169996)

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


for 7 nights €593

  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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


for 7 nights €460

Last booked 2 days ago
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  • Sleeps3
  • Bedrooms2
  • PetsNo

    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 €353

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A fabulous, three-bedroom home resting in Matlock, Derbyshire. Countryside views. Near National Park. Close to amenities and attractions. Woodburning stove. Stylish. Matlock Bath 2.5 miles; Bakewell 9.3 miles. (Ref. 1118940)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 10% off - Mon 29th Dec 2025 to 2nd Jan 2026


for 7 nights €672