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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    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

7 nights from £709

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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

7 nights from £501

Last booked 2 days ago
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    5.0

    Sykes Rating

Belgrano is a charming detached house in Matlock Bath, Derbyshire, boasting a hot tub, pet-friendly policies and a barbecue with views of Matlock Bath. Matlock 2.9 miles; Bakewell 9.8 miles. (Ref. 1155098)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Fri 5th Sep to 8th Sep 2025

7 nights from £922

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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 £409

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    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
  • 5% off - Sat 3rd May to 2nd Aug 2025

7 nights from £668

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from £347

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Sykes Rating

Cosy traditional barn conversion set in wooded valley near the High Peak Trail just outside Cromford. Character features. Great touring base. Matlock 5 miles. (Ref. 914759)

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

7 nights from £519

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    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

7 nights from £534

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    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

7 nights from £463

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

Smithy Cottage, a well-appointed, two-bedroom cottage rests in Barlow near Chesterfield, Derbyshire. Near National Park. Contemporary. Close to amenities. Private driveway. Chatsworth 9.1 miles; Bakewell 10.6 miles; Matlock 12.8 miles. (Ref. 1132596)

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

7 nights from £424

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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 £608

Last booked 2 days ago
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  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    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
  • £133 off - Sat 28th Jun to 5th Jul 2025

  • £121 off - Sat 19th Jul to 26th Jul 2025

  • £124 off - Sat 9th Aug to 16th Aug 2025

7 nights from £553

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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 £469

  • Sleeps3
  • Bedrooms2
  • PetsNo

    5.0

    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 £375

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A charming two-bedroom semi-detached house resting in Ashover, Derbyshire. Family-friendly. Smart TV. Near a river. Matlock 4.6 miles, Chesterfield 6.7 miles. (Ref. 1072527)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £415

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Sykes Rating

A charming semi-detached property resting in Baslow, Derbyshire. Garden. Off-road parking. Close to a pub. Calver 2.6 miles; Bakewell 4.6 miles; Sheffield 15.6 miles. (Ref. 1133131)

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

7 nights from £1170

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    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 £666

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    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 £557

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    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 £573

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

A lovely stone-built annexe on the edge of the village of Rowsley, near Bakewell. En-suite, Smart TV, WiFi. Perfectly placed to explore Chatsworth, Bakewell, Matlock and Matlock Bath. Bakewell 3 miles. (Ref. 945481)

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

7 nights from £527