Popular property types See all properties

24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Holiday Cottages Chesterfield

REFINE SEARCH

Your Chesterfield, Derbyshire search returned 166 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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

7 nights from £558

  • Sleeps10
  • Bedrooms5
  • PetsYes

    3.9

    Good

  • Sykes rating

The House at The Sitwell Arms is a wonderful, detached house resting in Renishaw, Derbyshire. Close to shop and pub. Near Peak District National Park. Worksop 10.3 miles; Sheffield 10.3 miles; Doncaster 22.4 miles. (Ref. 1134832)

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

7 nights from £1508

  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8

    Good

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

A stone-built semi detached cottage on the peaceful Darwin Lake Holiday Village. Three bedrooms with en-suites. Lake and woodland walks on-site. Matlock 3.2 miles. (Ref. 947282)

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

7 nights from £815

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.1

    Good

  • Sykes rating

This detached bungalow is situated in the village of Dore in Sheffield. Orangery. Four bedrooms. Pet friendly. Garden with patio area. Sheffield 6 miles. (Ref. 913256)

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

7 nights from £968

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Wonderful, spacious cottage on the outskirts of Pilsley village. En-suite, hot tub. Modern features. Superb accommodation for a family. Matlock 10 miles. (Ref. 932702)

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

7 nights from £499

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    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

7 nights from £607

Last booked 2 days ago
See more details
  • Sleeps7
  • Bedrooms3
  • PetsNo

    3.3

  • Sykes rating

This pleasant three-bedroom cottage rests in Darley Moor near Two Dales, Derbyshire. Dishwasher. Hot tub. Lakeside views. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129126)

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

7 nights from £474

  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A charming duplex apartment set in a Grade II listed building in Cuckney, Nottinghamshire. Character features. Off-road parking. En-suite bathrooms. Mansfield 7.1 miles; Sheffield 22.9 miles; Nottingham 24.2 miles. (Ref. 1116401)

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

7 nights from £719

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.0

    Good

  • Sykes rating

An inviting three-bedroom cottage resting in Hollingwood, Derbyshire. Child and pet-friendly. Close to amenities. Off-road parking. Brimington 0.7 miles; Barrow Hill 1.4 miles; Chesterfield 3.5 miles; Sheffield 12.7 miles. (Ref. 1076069)

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

7 nights from £392

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.1

    Good

  • Sykes rating

This beautifully-presented cottage is nestled in Bakewell, Derbyshire. Central location. Smart TV. En-suite bedroom. Matlock 8.7 miles; Chatsworth 10 miles; Buxton 12.7 miles. (Ref. 1131999)

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

7 nights from £669

  • Sleeps7
  • Bedrooms2
  • PetsNo

    4.3

    Good

  • Sykes rating

First floor of former carriage house in the Derbyshire village of Cromford. World Heritage Site. Listed building. Open-plan. Exposed stone and beams. En-suites. (Ref. 953526)

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

7 nights from £517

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Outstanding, unique converted water tank. Rurally located with amazing views that reach Chatsworth House. Open plan living, character features. Wonderful base for the Peak District. Bakewell 8 miles. (Ref. 903901)

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

7 nights from £713

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    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

7 nights from £611

  • 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
  • 10% off - Mon 11th Nov to 31st Dec 2024

7 nights from £1109

  • 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

7 nights from £620

Last booked yesterday
See more details
  • 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

7 nights from £653

  • 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

7 nights from £771

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4

    Good

  • Sykes rating

A charming one-bedroom cottage resting in Ashover, Derbyshire. Close to Peak District National Park. Countryside views. Studio-layout. Private decking. Close to walking trails. Matlock 3.3 miles; Chesterfield 8.1 miles. (Ref. 1113330)

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

7 nights from £377

  • Sleeps7
  • Bedrooms3
  • PetsNo
  • Sykes rating

This splendid three-bedroom property is perched in Darley Moor near Two Dales, Derbyshire. Lakeside views. Smart TV. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129130)

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

7 nights from £474

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

This delightful three-bedroom cottage rests in Darley Moor, near Two Dales, Derbyshire. Open-plan. Bedrooms with en-suites. Near a National Park. Matlock 3.2 miles; Bakewell 8.5 miles. (Ref. 1129127)

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

7 nights from £487