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.

Winster Cottages

REFINE SEARCH

Your Winster, Derbyshire search returned 180 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
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

11 The Hill is a wonderful, three-bedroom abode resting in Cromford, Derbyshire. Near Peak District National Park. Matlock Bath 1.2 mile; Matlock 2.6 miles; Bakewell 12.5 miles. (Ref. 1135369)

  • Wi-fi
  • Baby-friendly

7 nights from £433

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A historic holiday home resting Middleton-by-Youlgrave near Bakewell, Derbyshire. Woodburning stove. Character features. In the Peak District National Park. Pet-friendly. Matlock 10.9 miles; Buxton 12 miles; Chatsworth 12.2 miles. (Ref. 1123067)

  • Wi-fi
  • Washing machine

7 nights from £403

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Lovely single-storey cottage, with large enclosed garden, in the pretty Peak District village of Biggin-by-Hartington. Surrounded by beautiful countryside with plenty of walking and cycling opportunities. Buxton 12 miles. (Ref. 931808)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £484

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A characterful chocolate box cottage, resting in Youlgreave, Derbyshire. Original features. Pet-friendly. Close to amenities. Woodburning stove. Bakewell 3.5 miles; Buxton 13.2 miles; Leek 18.4 miles. (Ref. 1106936)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £453

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A charming two bedroom cottage tucked away in Hackney, in Derbyshire. Woodburning stove. Rural. Garden. Countryside views. Matlock 1.6 miles; Bakewell 7.1 miles; Ashbourne 15.2 miles. (Ref. 1055677)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £429

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

A stone-fronted, two-bedroom cottage located in the rural village of Over Haddon near Bakewell, Derbyshire. Woodburning stove. Pet-friendly. In National Park. On-site facilities. Chatsworth 13 miles; Buxton 10.6 miles; Matlock 11.7 miles. (Ref. 1130152)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Games room

7 nights from £557

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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)

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

7 nights from £389

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • 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)

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

7 nights from £597

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A lovely barn conversion with wonderful views. Cosy and welcoming, large garden. Walks from the door. Wirksworth 3 miles. (Ref. 18971)

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

7 nights from £307

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A traditional three-storey cottage situated in the village of Wirksworth, Derbyshire. Near National Park. Splendid countryside views. Matlock 4.5 miles; Ashbourne 9.4 miles; Bakewell 12.6 miles. (Ref. 1058638)

  • Wi-fi
  • Baby-friendly

7 nights from £330

  • Sleeps2
  • Bedrooms1
  • PetsYes
  • Sykes rating

A traditional one-bedroom cottage resting in Over Haddon near Bakewell, Derbyshire. In a National Park. Off-road parking. Dishwasher. Buxton 10.4 miles; Matlock 11.7 miles; Chatsworth 13 miles. (Ref. 1130154)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly
  • Games room

7 nights from £492

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A charming, mid-terrace cottage settled in Wirksworth, Derbyshire. Woodburning stove. On-street parking. Near the Peak District National Park. Matlock 4.4 miles; Crich 5.2 miles; Belper 6.8 miles. (Ref. 1094672)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £393

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A delightful, terraced cottage in the heart of Bakewell, Derbyshire. Within Peak District National Park. Romantic. Permit parking. Enclosed patio. Pet-friendly. Chatsworth 9.7 miles; Buxton 12.4 miles; Sheffield 17.3 miles. (Ref. 1134730)

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

7 nights from £470

  • 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

7 nights from £565

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Churchside House is a charming, three-bedroom holiday cottage resting in Matlock, Derbyshire. Close to amenities. Near a National Park. Electric fire. Matlock Bath 2.8 mile; Bakewell 8.9 miles. (Ref. 1105058)

  • Dishwasher
  • Washing machine

7 nights from £454

Last booked 2 days ago
See more details
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This terraced stone cottage is situated in Wirksworth, Derbyshire. WiFi. Woodburner. Matlock 6 miles. (Ref. 955081)

  • Wi-fi
  • Washing machine

7 nights from £328

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This studio property is set in the heart of Bakewell, Peak District National Park. Modern interior. Charming courtyard. Central location. (Ref. 989667)

  • Wi-fi

7 nights from £312

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Bear Cottage, a pretty terraced cottage situated in the town of Cromford in Derbyshire, close to a shop and a pub, and the Peak District National Park. Matlock Bath 1.2 miles; Wirksworth 1.9 miles; Peak District National Park 7.2 miles. (Ref. 1100050)

  • Wi-fi
  • Baby-friendly

7 nights from £359

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Single-storey barn conversion on owner's farm by the village of Hartington, Derbyshire. Ideal for couples or a small family. All ground floor. Bakewell 10 miles; Buxton 10 miles. (Ref. 996655)

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

7 nights from £277

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • 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

7 nights from £1301