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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 173 cottages

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  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.9

    Outstanding

  • 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


for 7 nights £1596

Last booked yesterday
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  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.6

    Outstanding

  • 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
  • £157 off - Fri 23rd Jan to 30th Jan 2026

  • £202 off - Fri 20th Feb to 27th Feb 2026

  • £156 off - Fri 27th Feb to 6th Mar 2026


for 7 nights £778

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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


for 7 nights £330

  • 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

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • 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


for 7 nights £552

Last booked yesterday
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  • 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 £603

  • Sleeps15
  • Bedrooms5
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Wonderful Grade ll listed former coaching inn on edge of Peak National Park, close to village of Holmesfield. First class accommodation, outstanding views. Games room, hot tub. Bakewell 10 miles. (Ref. 2564)

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


for 7 nights £1942

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A quaint cottage nestled in the charming village of Crich in Derbyshire. Woodburning stove. Bike storage. Pet friendly. Matlock 6.4 miles; Bakewell 14.9 miles; Nottingham 18.3 miles. (Ref. 1038762)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £420

Last booked yesterday
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  • 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 £427

Last booked 5 hours ago
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A well-presented, detached cottage nestled in the centre of Matlock, Derbyshire. Smart TV. South-facing terrace. Off-road parking. Bakewell 10.2 miles. (Ref. 1064755)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • £125 off - Fri 20th Feb to 27th Feb 2026

  • £52 off - Fri 27th Feb to 6th Mar 2026


for 7 nights £595

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A splendid one-bedroom single-storey cottage settled in Alfreton near Oakerthorpe, Derbyshire. Pet and child friendly. Hot tub. Off-road parking. Crich 2.8 miles; Matlock 8.3 miles. (Ref. 991273)

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


for 7 nights £390

Last booked 6 hours ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Matlock Maisonette is situated in Matlock in Derbyshire. Duplex apartment. Far-reaching views. Stunning terrace. Central location. Allocated parking. Bakewell 8.6 miles. Alfreton 9.2 miles. Sheffield 22.5 miles. (Ref. 1153088)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £562

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

9 White Edge Close is a pleasing, semi-detached home located in Chesterfield in Derbyshire, enjoying close proximity to the Peak District National Park. Matlock 10.2 miles; Chatsworth 9.4 miles; Bakewell 12.7 miles. (Ref. 1168890)

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


for 7 nights £484

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely tastefully styled stone-built cottage, conveniently located in the pretty village of Stoney Middleton. Lovely views and secure bike storage. Bakewell 5.5 miles. (Ref. 940662)

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


for 7 nights £403

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


for 7 nights £362

Last booked 6 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Potters Cottage is a delightful, Victorian dwelling resting in Fulwood on the outskirts of Sheffield, South Yorkshire. Near National Park. Close to amenities. Stylish. Chesterfield 13.4 miles; Doncaster 24.6 miles. (Ref. 1140958)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £430

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Superb semi-detached stable conversion in small village of Ashover. En-suite shower room, off road parking. Beautifully renovated to highest of standards. Excellent base for walking, cycling and exploring the Peak District. Matlock 5 miles. (Ref. 927577)

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


for 7 nights £627

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Timeless cosy cottage with off street parking within a short stroll of the lovely bustling village of Bakewell. Accommodating up to six guests and a cosy woodburning stove makes Corner Cottage the perfect choice. Chatsworth 4 miles. (Ref. 926401)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £568

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Old Apothecary is a Grade II listed duplex apartment in Matlock Bath, near Matlock, Derbyshire. Close to a pub. Historic property. Riverside views. Matlock 1.6 miles; Peak District National Park 5.9 miles; Bakewell 9.6 miles. (Ref. 1139646)

  • Wi-fi
  • Dishwasher


for 7 nights £539

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A contemporary first-floor apartment in Clay Cross, Derbyshire. Pet-friendly. Countryside views. Close to amenities. Smart TV. Chesterfield 5.1 miles; Matlock 7.8 miles; Peak District National Park 9.6 miles. (Ref. 1065378)

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


for 7 nights £579