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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
A stone house with multiple windows and chimneys surrounded by grass and flowering plants at Hallfield Hall in Shirland near Higham
98
Shirland near Higham, Derbyshire, DE55
  • Sleeps14
  • Bedrooms6
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Hallfield Hall is a stunning house situated in Shirland, Derbyshire, boasting a hot tub, bar, snooker table, games room, cinema room, and enclosed garden. Alfreton 2.4 miles; Matlock Bath 8.4 miles; Bakewell 15.1 miles; Derby 15.6 miles. (Ref. 1169570)

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


for 7 nights £2520

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A stone house with a gravel area and plants outside at 33 Main Road Higham Derbyshire
31
Higham Derbyshire, Derbyshire, DE55
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • 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


for 7 nights £449

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A stone house near a curved paved driveway with grass and trees at The Old Chapel in Handley near Ashover
26
Handley near Ashover, Derbyshire, S45
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • 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


for 7 nights £420

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A white single-story house with a tiled roof and a concrete driveway at Cherry Fields in Bolsover
40
Bolsover, Derbyshire, S44
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Homely, detached bungalow set in the town of Bolsover in Derbyshire. Conservatory. Smart TV. Luxury dog kennel. (Ref. 962748)

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


for 7 nights £398

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A stone house with a garden and paved paths leading to outdoor seating at Rose Cottage in Matlock
43
Matlock, Peak District & Derbyshire Dales, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Rose Cottage is a charming, stone-built cottage settled into the bustling town of Matlock, Derbyshire. Close to National Park. Near shop, pub, and river. Matlock Bath 1.8 miles; Peak District National Park 5 miles, Bakewell 8.7 miles. (Ref. 958573)

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


for 7 nights £732

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A patio with black wicker chairs around a square glass table and brown lounge chairs at Christmas Cottage in Higham near Shirland
31
Higham near Shirland, Derbyshire, DE55
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • 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


for 7 nights £534

Last booked yesterday
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A stone house with a hedge lined walkway and a garden with purple flowers at 2 Snape Hill in Dronfield
30
Dronfield, Derbyshire, S18
  • 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 £508

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A stone building with pink flowers in front and farm buildings in the background at Shire Cottage at Top Butterley Farm in Tansley near Matlock
25
Tansley near Matlock, Derbyshire, S45
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A pleasant barn conversion situated near the village of Tansley in the Derbyshire Dales. Stunning views of Ogston Reservoir and countryside. Exposed beams. On working farm. Matlock 3 miles. (Ref. 969731)

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


for 7 nights £332

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A stone wall with plants in front and a metal gate leading to a patio with a table and chairs at Causeway Hideaway in Dore
32
Dore, South Yorkshire, S17
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Causeway Hideaway is a delightful, single-storey annexe resting in Dore, South Yorkshire. Romantic. Close to amenities. Stylish. Near National Park. Sheffield 5.4 miles; Chesterfield 11.7 miles. (Ref. 1133830)

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


for 7 nights £442

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Stone cottage with yellow door and blue metal benches outside at 1 Barley Cottages in Matlock
Offer
51
Matlock, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A fabulous, three-bedroom home resting in Matlock, Derbyshire. Countryside views. Near National Park. Close to amenities and attractions. Woodburning stove. Stylish. Matlock Bath 2.5 miles; Bakewell 9.3 miles. (Ref. 1118940)

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

  • £197 off - Fri 24th Jul to 31st Jul 2026

  • £168 off - Fri 14th Aug to 21st Aug 2026

  • £68 off - Fri 28th Aug to 4th Sep 2026


for 7 nights £690

Last booked yesterday
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A two-story brick house with hedges and a black metal gate at The Old Grocery in Barrow Hill near Chesterfield
25
Barrow Hill near Chesterfield, Derbyshire, S43
  • 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 £407

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A stone building with slate roof and wooden door surrounded by plants at Grove Farm Barn in Darley Dale
29
Darley Dale, Derbyshire, DE4
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A delightful stone-built barn conversion resting on the outskirts of Matlock, Derbyshire. Open-plan. Views. Off-road parking. Matlock 2.1 miles; Bakewell 6.8 miles; Ashbourne 15.4 miles. (Ref. 1063970)

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


for 7 nights £503

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A living room with two beige sofas a small ottoman a wood stove a wall-mounted television and a wooden beam on the ceiling at Smithy Cottage in Barlow near Chesterfield
27
Barlow near Chesterfield, Derbyshire, S18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • 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


for 7 nights £413

Last booked 7 hours ago
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A small brick building with arched windows surrounded by trees and grass at The Chapel in Brackenfield near Stretton Derbyshire
34
Brackenfield near Stretton, Derbyshire, Derbyshire, DE55
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

The Chapel is a converted methodist chapel situated in Brackenfield near Stretton, Derbyshire. Character features. Open-plan living. Lawned garden. Alfreton 4.6 miles; Chesterfield 9.6 miles. (Ref. 1140286)

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


for 7 nights £572

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A living room with sofas cushions a coffee table and a kitchen with black cabinets and a dining table with chairs at Number 4 Westmoreland in Two Dales
27
Two Dales, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Number 4 Westmoreland is a stylish ground-floor apartment, close to the Peak District in the village of Two Dales, Derbyshire. Matlock 2.5 miles; Bakewell 6.1 miles. (Ref. 1160185)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights £421

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Stone exterior of Lydgate Cottage with a pale door and windows and black drainpipes in Eyam
30
Eyam, Peak District, S32
  • 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 £836

Last booked yesterday
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A stone house with brown doors and windows and a garden with grass and a small tree near The Smithy in Grindleford near Calver
26
Grindleford near Calver, Peak District, S32
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A beautiful two-bedroom cottage resting in Grindleford, Derbyshire. Off-road parking.In the Peak District National Park. En-suite bedrooms. Smart TV. Eyam 3.1 miles; Baslow 3.6 miles; Bakewell 6.8 miles. (Ref. 1079242)

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


for 7 nights £598

Last booked yesterday
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A stone cottage with two white framed windows and a gravel driveway at Harebell Cottage in Curbar
27
Curbar, Peak District, S32
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Harebell Cottage is a delightful barn conversion resting in Curbar, Derbyshire. In National Park. Woodburning stove. Countryside views. Close to pub. Bakewell 6.1 miles; Sheffield 12.8 miles; Buxton 15.3 miles. (Ref. 1146083)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £610

Last booked 2 days ago
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An outdoor deck with a hot tub and wicker sofa overlooking a village and green hills at Barncroft in Tansley near Matlock
46
Tansley near Matlock, Derbyshire, DE4
  • Sleeps11
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Barncroft is an outstanding detached bungalow situated in Tansley, Derbyshire boasting a double-sided log burner, hot tub, and elevated countryside views. Matlock 2 miles; Chesterfield 10.3 miles; Sutton-in-Ashfield 13.5 miles. (Ref. 1158073)

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


for 7 nights £1363

Last booked 6 hours ago
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Stone exterior of a two story house with windows and a grey door labeled church cottage in Bakewell
36
Bakewell, Peak District, DE45
  • 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 6 hours ago
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