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Holiday Cottages Chesterfield

Your Chesterfield, Derbyshire search returned 187 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This gorgeous three-storey cottage lies in Bakewell, Derbyshire. Enclosed garden. No pets. Bedroom with en-suite. Off-road parking. Chatsworth 9.6 miles; Matlock 8.3 miles; Buxton 12.3 miles. (Ref. 1064674)

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


for 7 nights £852

Last booked 9 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Oakwood Lodge is a charming, detached holiday home in Tansley, Derbyshire. Countryside views. Near the Peak District National Park. Pet-friendly. Matlock 1.7 miles; Bakewell 10.2 miles; Derby 18.4 miles. (Ref. 1147569)

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


for 7 nights £658

Last booked 2 days ago
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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


for 7 nights £1189

Last booked 8 hours ago
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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 £742

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A superb two-bedroom bungalow resting on the outskirts of Dronfield, near Chesterfield, Derbyshire. Family-friendly. Large partially enclosed garden. Dog friendly. Peak District. Bakewell 12.8 miles; Matlock 13.2 miles. (Ref. 1084691)

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


for 7 nights £595

  • 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 £1622

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Wayside Cottage is a delightful rural retreat near Matlock in Derbyshire with communal gardens, beautiful views and well-presented interior. Bakewell 9.7 miles, Sheffield 21.7 miles. (Ref. 1198441)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £330

Last booked yesterday
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  • 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 £399

Last booked 2 days ago
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  • 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 £672

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A delightful log cabin based just outside of the village of Rowsley in Derbyshire. Open plan modern accomodation. En-suite. Pet friendly. Rowsley 5 miles. Matlock 5 miles. (Ref. 936154)

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


for 7 nights £476

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This characterful terraced property resides in Chesterfield, Derbyshire. Enclosed garden. Conservatory. Smart TV. Near a National Park. Matlock 10.6 miles; Chatsworth 10 miles; Bakewell 14.1 miles. (Ref. 1122937)

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


for 7 nights £648

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Wigley Farm House Cottage is a fabulous pet-friendly bungalow near Chesterfield, Derbyshire, boasting a woodburning stove, a hot tub and countryside views. Chatsworth 6.7 miles; Bakewell 8.3 miles; Matlock 9.9 miles. (Ref. 1182208)

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


for 7 nights £714

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    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 £534

  • 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 £775

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This family-friendly, semi-detached cottage rests in Matlock, Derbyshire. Woodburning stove. Pet-friendly. Enclosed gardens. Close to amenities. Matlock Bath 2.5 miles; Bakewell 8.8 miles; Chesterfield 9.6 miles. (Ref. 1092561)

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


for 7 nights £451

  • 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 £1531

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Oakwood Mews is a stylish, single-storey holiday home nestled in Tansley, Derbyshire, boasting underfloor heating and a warm welcome for two pets. Matlock 1.9 miles. (Ref. 1194458)

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


for 7 nights £487

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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 £469

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Horsedale Barn is a charming farm stay ideal for couples, nestled in the village of Bonsall in Derbyshire, on the edge of the Peak District National Park. Matlock Bath 3.6 miles; Matlock 4.6 miles; Bakewell 9.9 miles. (Ref. 1161151)

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


for 7 nights £472

Last booked 7 hours ago
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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 £570