Popular property types See all properties

Holiday Cottages Chesterfield

Your Chesterfield, Derbyshire search returned 195 cottages

REFINE SEARCH
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

How reviews work

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

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    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 From €474

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €810

Last booked 2 days ago
See more details
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Peak Avenue Retreat is a charming holiday home, set over three floors, situated in the lovely village of Wingerworth near Chesterfield in Derbyshire. Matlock 9.4 miles; Chatsworth 10.2 miles; Bakewell 14.1 miles. (Ref. 1172926)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €533

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Laneside Barn featuring a Freestanding Bath, is a romantic barn conversion nestled in the heart of the pretty Peak District National Park in Calver, a quaint village in Derbyshire. Baslow 1.6 miles; Eyam 2.1 miles; Bakewell 4.7 miles. (Ref. 1207012)

  • Wi-fi


for 7 nights From €441

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €505

  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Coach House, a stunning, pet-friendly house nestled in the village of Holloway in Derbyshire, featuring a woodburning stove, and off-road parking. Matlock Bath 4.1 miles; Matlock 4.4 miles; Peak District National Park 9 miles. (Ref. 1161872)

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


for 7 nights From €955

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From €544

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    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
  • 20% off - Mon 26th Oct to 2nd Nov 2026


for 7 nights From €1791

  • Sleeps16
  • Bedrooms8
  • Pet FriendlyNo

    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 From €1847

Last booked 2 hours ago
See more details
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

2 Bentley Bridge Cottages is a charming, family and pet-friendly cottage in Matlock, Derbyshire, boasting original features and a woodburning stove. Matlock Bath 3.1 miles; Bakewell 9.1 miles. (Ref. 1205377)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €510

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From €570

Last booked yesterday
See more details
  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher


for 7 nights From €975

Last booked 2 days ago
See more details


for 7 nights From €12564

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

A lovely stone-built annexe on the edge of the village of Rowsley, near Bakewell. En-suite, Smart TV, WiFi. Perfectly placed to explore Chatsworth, Bakewell, Matlock and Matlock Bath. Bakewell 3 miles. (Ref. 945481)

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


for 7 nights From €600

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Yew Tree Cottage is a delightful, pet-friendly holiday cottage resting in the charming town of Matlock in Derbyshire with an enclosed decked balcony. Matlock Bath 1.9 miles; Bakewell 8.6 miles. (Ref. 1174717)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From €518

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    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 From €404

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From €498

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From €510

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A quaint, mid-terrace cottage settled in the village of Matlock, Derbyshire. Woodburner. Enclosed garden. Scenic location. Bakewell 4.7 miles; Matlock Bath 5 miles. (Ref. 1094150)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 20% off - Sun 27th Sep to 4th Oct 2026

  • 20% off - Sat 31st Oct to 7th Nov 2026

  • 20% off - Sat 7th Nov to 14th Nov 2026


for 7 nights From €581