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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 170 cottages

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  • Sleeps10
  • Bedrooms7
  • PetsYes
  • Sykes rating

Five Acres is a large, fun-filled holiday home on the outskirts of pretty market town of Chesterfield, Derbyshire, with a hot tub, sauna and games room. Matlock 9.8 miles; Chatsworth 10.1 miles; Bakewell 13.4 miles; Sheffield 14.8 miles. (Ref. 1166348)

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

7 nights from $9307

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A pretty red brick terraced property, resting in the village of Creswell, Derbyshire. Spacious interior. Off-road parking. Smart TV. WiFi. Worksop 6.6 miles; Sheffield 14.9 miles; Matlock 19.9 miles. (Ref. 1021053)

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

7 nights from $506

  • Sleeps7
  • Bedrooms3
  • PetsNo
  • Sykes rating

This fabulous three-bedroom cottage rests in Darley Moor, near Two Dales, Derbyshire. Lakefront. Near a National Park. Bedrooms with en-suites. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129117)

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

7 nights from $1414

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Good

  • Sykes rating

Whim Cottage, a traditional dwelling set in the village of Hathersage, Derbyshire. Woodburning stove. Good transport links. Enclosed garden. Pet-friendly. Curbar 6.3 miles; Castleton 6.5 miles. (Ref. 1135670)

  • Wi-fi
  • Off-road parking

7 nights from $568

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This traditional mid-terrace property rests at the heart of the Peak District. Brilliant base for walking. Private enclosed courtyard. Calver 1 mile. (Ref. 967600)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $836

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Lovely one bedroom modern cottage with fantastic walks from the doorstep, on the edge of Rowsley village. Great views located between Bakewell and Matlock. Ideal romantic retreat. Bakewell 3 miles. (Ref. 941567)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Sky TV

7 nights from $482

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Lovely romantic cottage with some wonderful features, including stone fireplace with woodburner. WiFi. A short walk to village amenities, making a perfect romantic break. Matlock 3 miles. (Ref. 923214)

  • Wi-fi

7 nights from $495

  • Sleeps4
  • Bedrooms1
  • PetsYes
  • Sykes rating

2 Rock Mill Holiday Apartments is a contemporary ground-floor apartment in the heart of the Peak District National Park, in Stoney Middleton, Derbyshire. Eyam 0.8 miles; Baslow 2.8 miles; Bakewell 5.9 miles. (Ref. 1165721)

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

7 nights from $645

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A charming mews cottage resting in Stoney Middleton, Derbyshire. Barbecue. En-suite bedrooms. In the Peak District National Park. Eyam 1.2 miles; Bakewell 5.6 miles; Chapel-en-le-Frith 12.1 miles. (Ref. 1070240)

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

7 nights from $1323

Last booked 2 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A truly breath-taking converted water tower on the outskirts of Bolsover, Derbyshire. Woodburning stove. Stylish and contemporary. Romantic. Off-road parking. 6 acres of land. Chesterfield 7.7 miles; Sherwood Forest 9.7 miles; Sheffield 16.6 miles. (Ref. 1116427)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $1379

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A wonderful ground-floor apartment in a Grade II listed building near Cuckney, Nottinghamshire. Ground-floor living. Dog-friendly. Original features. Family-friendly. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116402)

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

7 nights from $684

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Stylish and spacious townhouse, situated in Matlock, Derbyshire. Hot tub. Matlock Bath 1 mile. (Ref. 968285)

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

7 nights from $1464

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Good

  • Sykes rating

An end-terrace barn conversion near Barlow. With woodburner, open plan living area. Ideal touring base on edge of Peak District National Park. Barlow 1 mile. (Ref. 939316)

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

7 nights from $477

  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

8 Inns Lane is a delightful, three-bedroom holiday home resting in South Wingfield, Derbyshire. Near a National Park. Close to pub. Off-road parking. Pet-free. Matlock 6.4 miles. (Ref. 1142655)

  • Wi-fi
  • Washing machine

7 nights from $485

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Outstanding, semi-detached stone- built cottage. In the picturesque village of Baslow. Luxuriously appointed throughout. A lovely, romantic retreat for couples. Chatsworth 1 mile. (Ref. 939173)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $954

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A semi-detached property nestled in the market town of Bakewell, Derbyshire. Smart TV. Close to amenities. In National Park. Electric fire. Matlock 8.5 miles; Chatsworth 9.2 miles. (Ref. 1104863)

  • Wi-fi
  • Washing machine

7 nights from $648

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Churchside House is a charming, three-bedroom holiday cottage resting in Matlock, Derbyshire. Close to amenities. Near a National Park. Electric fire. Matlock Bath 2.8 mile; Bakewell 8.9 miles. (Ref. 1105058)

  • Dishwasher
  • Washing machine
  • 5% off - Sun 29th Jun to 22nd Jul 2025

7 nights from $679

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A characterful terrace cottage set in the idyllic village of Darley Bridge, on the edge of the Peak District National Park. Countryside retreat. Original features. Pet-friendly. Matlock 2.9 miles; Bakewell 6.1 miles; Buxton 18.4 miles. (Ref. 1058614)

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

7 nights from $525

Last booked 2 days ago
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  • Sleeps14
  • Bedrooms7
  • PetsNo

    4.0

    Good

  • Sykes rating

A Grade I listed property in a tranquil and historic Derbyshire setting in the village of Cromford. Near Peak District National Park. Off-road parking. Large garden. Matlock Bath 1.2 miles; Matlock 2.3 miles; Bakewell 10.8 miles. (Ref. 1050404)

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

7 nights from $2240

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

The Botanical Flat 1, a charming, three-bedroom apartment in Sheffield, South Yorkshire. Pet-friendly. Close to amenities. Near Botanical Gardens & Peak District National Park. Sheffield 2.1 miles; Matlock 21.4 miles; Leeds 37.1 miles. (Ref. 1148552)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $711