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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 173 cottages

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  • 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


for 7 nights £682

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A lovely, character cottage in the World Heritage village of Cromford. WiFi. Beams, stone walls and a patio garden with furniture. Wonderful base for exploring the Derbyshire Dales. Matlock 3 miles. (Ref. 903532)

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


for 7 nights £494

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely, detached house in the centre of Barrow Hill. Three bedrooms, WiFi and pet-friendly. Chesterfield 5.5 miles. (Ref. 933885)

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


for 7 nights £405

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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


for 7 nights £472

Last booked 7 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Rock Mill Holiday Apartments is a stunning, third-floor apartment resting in Stoney Middleton, near Calver, Derbyshire. In Peak District National Park. Off-road parking. EV Charging. Calver 1 mile; Bakewell 5.7 miles; Sheffield 12.9 miles. (Ref. 1130694)

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


for 7 nights £470

  • 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


for 7 nights £715

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


for 7 nights £501

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This superb lodge is situated near to South Wingfield, near Derbyshire. En-suite. Woodburner. Chesterfield 11.6 miles; Mansfield 12.9 miles. (Ref. 1005401)

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


for 7 nights £556

  • 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
  • £100 off - Sat 17th Jan to 24th Jan 2026

  • £104 off - Sat 24th Jan to 31st Jan 2026

  • £98 off - Sat 31st Jan to 7th Feb 2026

  • £100 off - Sat 7th Feb to 14th Feb 2026

  • £110 off - Sat 14th Feb to 21st Feb 2026

  • £93 off - Sat 21st Feb to 28th Feb 2026

  • £101 off - Sat 28th Feb to 7th Mar 2026


for 7 nights £450

Last booked today
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A charming single-storey, stone-fronted cottage, resting in Stone Edge, Derbyshire. Close to Peak District National Park. Woodburning stove. Countryside views. Open-plan. EV charging point. Ashover 3.6 miles; Chesterfield 4.9 miles; Matlock 6 miles. (Ref. 1099455)

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


for 7 nights £696

  • 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


for 7 nights £530

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Lydgate Cottage is an original cottage sitting in the heart of Eyam, Derbyshire. Hot tub. Pet-friendly. Woodburning stove. Near amenities. In National Park. Tideswell 5.2 miles; Bakewell 6.8 miles. (Ref. 1066992)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher


for 7 nights £788

Last booked yesterday
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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


for 7 nights £1498

  • 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


for 7 nights £693

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Outstanding, unique converted water tank. Rurally located with amazing views that reach Chatsworth House. Open plan living, character features. Wonderful base for the Peak District. Bakewell 8 miles. (Ref. 903901)

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


for 7 nights £634

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    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


for 7 nights £605

  • 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 £528

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

A lovely, detached Baslow cottage with original features and character charm. A cosy, welcoming Baslow cottage close to the Chatsworth Estate, beautiful walks and nearby Bakewell. (Ref. 4126)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £445

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Holbein is a delightful single-storey, studio-style lodge resting in Hackney, Derbyshire, this pet friendly abode has a woodburning stove and hot tub. Matlock Bath 2 mile; Bakewell 7.1 miles. (Ref. 1164247)

  • Off-road parking
  • Ground floor bedroom
  • Hot Tub


for 7 nights £561

Last booked 7 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A delightful stone-built cottage nestled in Cromford, Derbyshire. Open-plan. Woodburning stove. Pet-friendly. Matlock 2.5 miles. (Ref. 1062326)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • £93 off - Fri 16th Jan to 23rd Jan 2026

  • £93 off - Fri 23rd Jan to 30th Jan 2026


for 7 nights £412