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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • 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

7 nights from £365

Last booked yesterday
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  • 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

7 nights from £1172

  • 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

7 nights from £516

  • 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

7 nights from £1597

Last booked yesterday
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  • 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

7 nights from £394

  • 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

7 nights from £488

  • 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

7 nights from £471

  • 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

7 nights from £1525

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • 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 £524

  • 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 £502

  • 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
  • £52 off - Fri 5th Dec to 12th Dec 2025

  • 15% off - Mon 29th Dec 2025 to 2nd Jan 2026

7 nights from £602

  • 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

7 nights from £448

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Homely, detached bungalow set in the town of Bolsover in Derbyshire. Conservatory. Smart TV. Luxury dog kennel. (Ref. 962748)

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

7 nights from £423

  • 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

7 nights from £410

  • 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

7 nights from £304

Last booked yesterday
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  • 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

7 nights from £559

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • 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 £380

Last booked yesterday
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  • 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

7 nights from £1465

  • 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

7 nights from £1349

  • Sleeps9
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Rowtor is a wonderfully-adorned barn conversion residing in Birchover near Winster, Derbyshire. In the Peak District National Park. Study. Mezzanine study. Ground-floor bedrooms and open-plan living. Character. Bakewell 5.6 miles; Matlock 6.3 miles. (Ref. 1120844)

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

7 nights from £717

Last booked yesterday
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