Holiday Cottages Chesterfield

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

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Holiday Cottages Chesterfield

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Your Chesterfield, Derbyshire search returned 176 cottages

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A small wooden house on a grassy hill with a stone retaining wall and trees at Cedar Holme in Wingerworth
20
Wingerworth, Derbyshire, S42
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A snug single-storey lodge situated in the quaint village of Wingerworth in Derbyshire. Pet friendly. Bike storage. WiFi. Chesterfield 2.8 miles; Matlock 8.4 miles; Ripley 11.6 miles. (Ref. 1073399)

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


for 7 nights £455

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A stone house with large triangular windows and a garden with patio furniture and umbrella at Swallows Barn in Walton near Chesterfield
42
Walton near Chesterfield, Derbyshire, S42
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A stunning barn conversion resting in Walton near Chesterfield, Derbyshire. Secluded. Near the Peak District National Park. Enclosed garden. Romantic. Matlock 7.2 miles; Bakewell 10.8 miles. (Ref. 1087716)

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


for 7 nights £649

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An outdoor patio with a round wooden table and plastic chairs next to a wooden building with glass railing at Stables Lodge in Wingerworth
28
Wingerworth, Derbyshire, S42
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A superb two-bedroom, wooden-cladded lodge resting in Wingerworth, Derbyshire. Pet-friendly. Fantastic views. Off-road parking. Chesterfield 3.1 miles; Matlock 7.3 miles; Bakewell 11.9 miles. (Ref. 1076095)

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


for 7 nights £567

Last booked 2 days ago
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A wooden lodge with a sign reading Harry's Lodge on a lawn with trees and a stone wall at Harry's Lodge in Ashover
26
Ashover, Derbyshire, S45
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming lodge set in a lovely paddock, a few miles from the village of Ashover. Open-plan living. Dishwasher. Country setting. Chesterfield 5.1 miles; Matlock 5.8 miles. (Ref. 1123841)

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


for 7 nights £490

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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 £450

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A stone house with a garden and paved paths leading to outdoor seating at Rose Cottage in Matlock
43
Matlock, Derbyshire, 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 £742

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A paved driveway with iron gates leading to a stone house with multiple windows near Chesterfield
64
near Chesterfield, Derbyshire, S45
  • Sleeps10
  • Bedrooms5
  • PetsNo

    5.0★

    Perfect

  • 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 £1600

Last booked yesterday
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A stone building with a red door and hanging flower baskets next to a wooden gate with a sign for free range eggs at The Old Chapel in Crich
19
Crich, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Converted chapel. One en-suite bedroom. Private patio with furniture. Woodburning stove. Crich 3.3 miles. Matlock 4 miles. (Ref. 924332)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging


for 7 nights £386

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A stone exterior wall with green framed windows and a sliding glass door next to a garden bed and outdoor seating area at Temperance Croft Wadshelf near Chesterfield
40
Wadshelf near Chesterfield, Derbyshire, S42
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Temperance Croft is a charming, single-storey holiday cottage resting in the quaint little village of Wadshelf in Derbyshire which is ideal for couples. Chatsworth 5.4 miles; Bakewell 8.3 miles; Matlock 9.1 miles. (Ref. 1155313)

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


for 7 nights £399

Last booked 9 hours ago
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A patio area with chairs and small tables next to a house with trellises and plants at Moor Farm Cottage in Alton near Ashover
47
Alton near Ashover, Derbyshire, S42
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A beautiful, single-storey holiday home encapsulated by the countryside in Alton near Ashover, Derbyshire. Ground-floor living. Hot tub. Barbecue. Gym. Countryside views. Smart TVs. Ashover 1.9 miles, Matlock 5.1 miles, Chesterfield 5.6 miles (Ref. 1129371)

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


for 7 nights £699

Last booked yesterday
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A house with a stone wall hedge and white gate with woodlands sign at Woodlands in Darley Dale
40
Darley Dale, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

An attractive dormer bungalow resting in Darley Dale, close to the Peak District National Park. Close to amenities. Off-road parking. Wheelchair friendly. Matlock 3.1 miles; Bakewell 5.5 miles; Ashbourne 15.4 miles. (Ref. 1077976)

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


for 7 nights £568

Last booked yesterday
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A brick detached house with tiled roof driveway and windows at Spire Haven in Chesterfield
30
Chesterfield, Derbyshire, S40
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stylish, detached holiday home resting in Chesterfield, Derbyshire. Enclosed garden. Close to amenities. Family-friendly. Matlock 10 miles; Chatsworth 10 miles; Bakewell 13 miles. (Ref. 1087361)

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


for 7 nights £707

Last booked yesterday
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A single story stone house with multiple windows and a double garage surrounded by grass and trees at Manor House in Chesterfield
38
Chesterfield, Derbyshire, S41
  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A marvellous ground floor, detached cottage on the edge of Chesterfield in the Peak District. En-suite wet rooms. WiFi. Children's play area. Enclosed garden. Chatsworth House 8 miles. Chesterfield 2 miles. (Ref. 904429)

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


for 7 nights £2213

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A stone cottage with a tiled roof and a small front garden enclosed by a stone wall and wooden gate at Woodthorpe Cruck Cottage in Old Tupton near Clay Cross
35
Old Tupton near Clay Cross, Derbyshire, S42
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A Grade II listed property, resting on the outskirts of Clay Cross. Woodburning fire. WiFi. Hot tub. Set in a 100 acres of farmland. Chesterfield 5 miles. (Ref. 945165)

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


for 7 nights £784

Last booked yesterday
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Stone cottage with yellow door and blue metal benches outside at 1 Barley Cottages in Matlock
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

  • 10% off - Mon 29th Dec 2025 to 2nd Jan 2026

  • £365 off - Fri 2nd Jan to 9th Jan 2026


for 7 nights £596

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A patio with metal chairs and a table with sunflowers and glasses overlooking a countryside view at The Bungalow@Barlow in Chesterfield
36
Chesterfield, Derbyshire, S18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    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

Last booked 2 days ago
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A stone house with multiple windows and chimneys surrounded by grass and flowering plants at Hallfield Hall in Shirland near Higham
64
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
  • Games room


for 7 nights £2548

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A stone house with a tiled roof and a garden with potted plants and outdoor furniture at The Gatehouse in Mansfield
50
Mansfield, Nottinghamshire, NG17
  • 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 £1210

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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 £862

Last booked 2 days ago
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A stone wall with a sign saying The Old Stables next to a window with curtains and a bench with green plants surrounding at The Old Stables Ashover near Matlock
26
Ashover near Matlock, Derbyshire, S45
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Beautiful stable conversion in owner's grounds in Ashover village. Rural location, countryside views, quality accommodation. Off road parking, front garden, en-suite shower room. Good walking and cycling. Matlock 5 miles. (Ref. 927574)

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


for 7 nights £787

Last booked yesterday
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