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Winster Cottages

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Your Winster, Derbyshire search returned 187 cottages

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  • Sleeps11
  • Bedrooms6
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An outstanding, stone-built barn conversion resting in Middleton near Youlgreave, Derbyshire. Hot tub. Bedrooms with en-suites. Woodburning stove. Winster 4.6 miles; Bakewell 6.6 miles; Matlock 9.8 miles. (Ref. 1079765)

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

7 nights from €2191

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Lovely terraced Peak District cottage in village of Winster. Woodburning stove, enclosed courtyard garden. Matlock 4.5 miles. (Ref. 21953)

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

7 nights from €505

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Romantic character cottage set in peace and tranquillity of the countryside, close to the village of Winster. One cosy double bedroom with en-suite shower room. Large lawned garden. Bakewell 6 miles. (Ref. 938599)

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

7 nights from €424

Last booked 9 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Jasmine Cottage is characterful, mid-terrace cottage in the centre of Winster, Derbyshire. Open fire. Roll-top bath. Rear courtyard. Near a shop and pub. Matlock 5.2 miles; Bakewell 6.6 miles. (Ref. 1151211)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from €518

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming stone-built cottage nestled in Elton, near Winster, Derbyshire. Romantic. Courtyard garden. Woodburning stove. Winster 1.2 miles; Matlock 6.4 miles; Bakewell 6.8 miles. (Ref. 1081190)

  • Wi-fi
  • Dishwasher

7 nights from €525

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

The Bottling Shed, a wonderful holiday retreat lying in the scenic Peak District in Matlock, Derbyshire. Romantic retreat. Hot tub. Open-plan. Balcony. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1048671)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from €592

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

An outstanding, detached barn conversion in village of Brassington, Derbyshire. Romantic retreat. Woodburner. Character feel. Matlock 7.9 miles. (Ref. 1098005)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €552

Last booked 2 days ago
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  • 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 €539

Last booked yesterday
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  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Charming semi-detached cottage on working farm close to Winster. Cosy character accommodation with old cruck beams and lovely countryside views. Bakewell 7.5 miles. (Ref. 2686)

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

7 nights from €381

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A beautiful detached stone-fronted cottage resting in the village of Winster, Derbyshire. In the Peak District National Park. Countryside views. Multi-level, terraced garden. Woodburning stove. Bakewell 6.9 miles; Matlock 5.3 miles. (Ref. 1113178)

  • Wi-fi
  • Washing machine
  • 5% off - Sat 15th Jun to 22nd Jun 2024

  • 10% off - Sat 6th Jul to 13th Jul 2024

  • €115 off - Sat 2nd Nov to 9th Nov 2024

7 nights from €509

  • Sleeps3
  • Bedrooms2
  • PetsYes

    3.8

    Good

  • Sykes rating

A character cottage set beside the River Bradford in the village of Youlgreave, Derbyshire. Pet-friendly. Idyllic setting. Electric fire. Bakewell 5.2 miles. (Ref. 1134211)

  • Wi-fi
  • Washing machine

7 nights from €518

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Cosy stone-built barn conversion on the owners' working livestock farm, two miles from Matlock. Large garden, pet-friendly. Walks from the doorstep. Opposite Matlock Golf Club. Bakewell 10 miles. (Ref. 929053)

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

7 nights from €412

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Charming semi-detached cottage in lovely Peak District village. Romantic retreat with fabulous views. Walking, cycling and watersports nearby. Matlock 8 miles. (Ref. 920228)

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

7 nights from €411

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Lovely terraced cottage overlooking river in pretty Peak village of Youlgreave. Ideal romantic retreat full of charm and character. National Park nearby. Bakewell 4 miles. (Ref. 2239)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from €387

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

An outstanding cottage. Retro and contemporary with wooden floors, underfloor heating, a woodburning stove and a well-equipped kitchen. Pretty gardens.WiFi Bakewell 5 miles. (Ref. 924952)

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

7 nights from €525

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful stone-built barn conversion resting on the outskirts of Matlock, Derbyshire. Open-plan. Views. Off-road parking. Matlock 2.1 miles; Bakewell 6.8 miles; Ashbourne 15.4 miles. (Ref. 1063970)

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

7 nights from €557

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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

7 nights from €483

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Lovely chocolate box cottage in centre of beautiful conservation village of Winster. Suitable for a family. Off road parking. Bakewell 6 miles. (Ref. 926728)

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

7 nights from €716

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.4

    Good

  • Sykes rating

A historic holiday home resting in the charming village of Middleton near Wirksworth, Derbyshire. Dog-friendly. Hot tub, Woodburning stoves. Front patio. Washing machine. Dishwasher. Matlock 4.8 miles; Bakewell 11.1 miles; Derby 15.5 miles. (Ref. 1088609)

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

7 nights from €1220

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

An impressive Georgian holiday cottage sitting within the conservation village of Winster, in the Peak District National Park. Woodburning stove. Original features. Surround-sound throughout. Matlock 5.3 miles; Chesterfield 12.5 miles. (Ref. 1035366)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from €809

Just Show Me Winster Cottages

Please find below a selection of personally inspected, self catering holiday cottages within 5 miles of Winster, Derbyshire. If you are looking for holiday cottages in Winster, Cumbria, please click here.

Enjoy the warmest hospitality with a break in a Winster cottage, located in an attractive conservation village at the heart of the National Park. It's a popular place with walkers - simply arm yourself with an OS Map and pair of sturdy boots, then plan a leisurely hour's ramble or a day-long trek.

Get to know Winster with a stroll along the main street, lined with impressive stone buildings (over 70 are listed in the village) and small, quirky cottages. Look out for Winster Hall with its distinctive Italian-style columns, the beautiful Dower House and the old Market Hall - the National Trust's first Derbyshire find and built with bricks rather than stone.

You'll find a couple of welcoming pubs serving traditional food, a handful of gift shops and a village shop/Post Office, run by the local community and offering everything you might need for filling your Winster cottage's fridge!

Book a Winster cottage for unique attractions!

Think Pancake Races, Wakes Week featuring exclusive Morris dances, the Winster Millennium Tapestry and the Secret Gardens of Winster - an annual event when villagers open their gardens to visitors and organise Gnome Hunts for the kids!

Local places of interest range from family attractions such as Gulliver's Kingdom and the Heights of Abraham to heritage mills, designer shopping and historic estates like Haddon Hall and Chatsworth. Breathtaking natural wonders include Harboro Rocks for fantastic rock climbing, the lofty limestone crag of High Tor and Robin Hood's Stride, an extraordinary tor of gritstone rocks set high on a ridge.

All kinds of reasons to browse Winster cottages, some of the very best cottages in the Peak District.