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
  • 10 Guests
  • 5 Bedrooms
  • Pets Yes

    4.0

    Sykes Rating

This fabulous five-bedroom property rests in Over Haddon near Bakewell, Derbyshire. Woodburning stove. Pet-friendly. Shared swimming pool. Chatsworth 13 miles; Buxton 10.6 miles; Matlock 11.7 miles. (Ref. 1128316)

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

7 nights from £1359

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    Sykes Rating

Oakwood Lodge is a charming, detached holiday home in Tansley, Derbyshire. Countryside views. Near the Peak District National Park. Pet-friendly. Matlock 1.7 miles; Bakewell 10.2 miles; Derby 18.4 miles. (Ref. 1147569)

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

7 nights from £670

Last booked yesterday
See more details
  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.7

    Sykes Rating

Stone, mid-terrace cottage nestled a short stroll away from the pretty market town of Bakewell. Woodburner. Off-road parking. WiFi. Shop 0.6 miles, pub 0.5 miles. (Ref. 974373)

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

7 nights from £573

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

    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

  • 3 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    Sykes Rating

A pretty, traditional cottage resting in Winster in the Derbyshire Dales, with country views. In a National Park. Matlock 5.5 miles; Bakewell 6.8 miles. (Ref. 1083119)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £429

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    Sykes Rating

A traditional stone cottage sitting in the rural village of Alderwasley. Woodburning stove. Superb country views. Ideal for families. Matlock 5.2 miles; Bakewell 13.5 miles. (Ref. 1017565)

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

7 nights from £594

  • 10 Guests
  • 5 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A fantastic five-bedroom detached house resting in Bakewell, Derbyshire. Pet-friendly. Woodburning stove. Off-road parking. Chatsworth 9.7 miles; Matlock 8.6 miles; Buxton 13.4 miles. (Ref. 921800)

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

7 nights from £1488

  • 2 Guests
  • 1 Bedroom
  • Pets No

    Sykes Rating

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

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

7 nights from £348

Last booked yesterday
See more details
  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.3

    Sykes Rating

Beautiful stone semi-detached cottage located near the rural village of Two Dales in Derbyshire. Lakeside views. Dog friendly. On-site fishing. Shop and pub 2.5 miles. (Ref. 981396)

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

7 nights from £795

7 nights from £462

  • 3 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    Sykes Rating

This superb stone barn conversion is located in Biggin, Derbyshire. Electric woodburner. WiFi. Open-plan living. Ashbourne 10 miles; Buxton 12 miles. (Ref. 1005520)

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

7 nights from £337

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.5

    Sykes Rating

A pretty country cottage residing in Over Haddon near Bakewell, Derbyshire. In a National Park. Shared games room. Pet-friendly. Chatsworth 13 miles; Buxton 10.6 miles; Matlock 11.7 miles. (Ref. 1129195)

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

7 nights from £793

  • 7 Guests
  • 3 Bedrooms
  • Pets No

    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 £536

  • 2 Guests
  • 1 Bedroom
  • Pets No

    5.0

    Sykes Rating

A charming detached property situated near the market town of Ashbourne in Derbyshire. Woodburning stove. WiFi. Ashbourne 8.7 miles. (Ref. 998284)

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

7 nights from £307

Last booked 2 days ago
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

This charming semi-detached cottage rests in Tansley, Derbyshire. Off-road parking. Woodburning stove. Pet-free. Garden with furniture. Matlock 1.7 miles. (Ref. 1061197)

  • Wi-fi
  • Off-road parking
  • Baby-friendly
  • 5% off - Mon 7th Apr to 3rd May 2025

7 nights from £520

7 nights from £314

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Lovely detached bungalow close to centre of the Derbyshire market town of Matlock. Edge of Peak District National Park. Bakewell 8 miles. (Ref. 5689)

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

7 nights from £519

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    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 £432

Last booked yesterday
See more details
  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

    Sykes Rating

Tor Barn, a delightful reverse-level cottage nestled in Winster, Derbyshire. Pet-friendly. Enclosed garden. Off-road parking. EV charging available. Matlock 5.3 miles; Bakewell 6.9 miles. (Ref. 1150081)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher

7 nights from £498

  • 3 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    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)

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

7 nights from £553