Winster Cottages

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Winster Cottages

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Your Winster, Derbyshire search returned 186 cottages

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An outdoor patio area with a green door and window on a stone building and a small seating area with a table and chairs at 34 Church Street Matlock
15
Matlock, Derbyshire, DE4
  • Sleeps3
  • Bedrooms2
  • PetsNo

    5.0

    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

7 nights from £375

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A living room with a sofa armchair fireplace wooden shelves and a large wall clock at Mouse Cottage in Bakewell
37
Bakewell, Peak District, DE45
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

A charming, two-bedroom cottage resting in Bakewell, Derbyshire. Close to amenities. In National Park. Characterful. Off-road parking. Log effect gas fire. Chatsworth 4.5 miles; Matlock 8.4 miles; Buxton 11.9 miles. (Ref. 929026)

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

7 nights from £601

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A stone building with slate roof and wooden door surrounded by plants at Grove Farm Barn in Darley Dale
31
Darley Dale, Derbyshire, DE4
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    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

7 nights from £503

Last booked 5 hours ago
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A stone cottage with wooden doors behind a wooden gate and stone walls surrounded by trees at The Dell in Winster
23
Winster, Peak District, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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 £372

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An open wooden door leading to a room with stairs and a checked blanket at The Sidings in Wirksworth
21
Wirksworth, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

Contemporary, cosy holiday home, a short stroll from the lovely little town of Wirksworth. En-suite bedroom. Woodburner. Patio with furniture. Romantic retreat. Carsington Water 4 miles. Matlock 6 miles. (Ref. 923305)

  • Wi-fi
  • Off-road parking

7 nights from £353

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A stone house with multiple windows and a gravel driveway behind metal gates with a stone wall and green grass at Shortner Croft in Biggin near Ashbourne
24
Biggin near Ashbourne, Peak District, SK17
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 £489

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A street view of stone brick houses with windows and doors including a blue door at The Hill in Cromford
10
Cromford, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

This lovely little stone cottage sits in the Derbyshire village of Cromford. Near Peak District National Park. WiFi. Matlock 3 miles. (Ref. 981522)

  • Wi-fi
  • Off-road parking

7 nights from £309

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A stone building with blue double doors and wooden stairs leading to a balcony at The Old Bakery Barn in Youlgrave
17
Youlgrave, Peak District, DE45
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

The first floor a converted barn in the Derbyshire village of Youlgrave in Derbyshire. Peak District National Park. Open-plan living. Pub and shop close by. Bakewell 4 miles. (Ref. 974921)

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

7 nights from £383

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A stone building with a dark tiled roof and wooden door with a small sign above at The Stables in Ashbourne
18
Ashbourne, Peak District, DE6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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

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An outdoor area with a stone wall wooden door wooden framed window and door flower pots and hanging basket at The Cow Shed in Alport near Bakewell
11
Alport near Bakewell, Peak District, DE45
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

Cosy, studio cottage in Alport near Youlgreave. Underfloor heating. Hot tub. Fantastic views. Wonderful walking opportunities nearby. Bakewell 3 miles. (Ref. 914085)

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

7 nights from £561

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A stone house with a gravel pathway and a metal gate surrounded by green bushes at The Mouse House in Elton near Winster
23
Elton near Winster, Peak District, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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 £454

Last booked 2 days ago
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Stone cottage entrance with a blue door and window with flower pots along a narrow stone pathway at The Hayloft in Winster
18
Winster, Peak District, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A lovely two-bedroom, (bookable with Ivy Cottage -1051655) detached stone annexe resting in Winster, Derbyshire. In a National Park. Smart TV. Romantic. Pet-free. Matlock 5.2 miles; Bakewell 6.5 miles. (Ref. 1063737)

  • Wi-fi
  • Ground floor bedroom

7 nights from £436

Last booked 2 days ago
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A backyard garden with grass shrubs stone wall patio furniture and a conservatory at Number 4 Westmoreland in Two Dales
27
Two Dales, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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 £425

Last booked 2 days ago
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An outdoor patio area with a hot tub and seating against a stone wall at The Bottling Shed in Oker near Matlock
23
Oker near Matlock, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    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 £520

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A stone house with a garden bench and red tulips in pots in front at Tor Barn in Winster
41
Winster, Peak District, DE4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    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 £475

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A stone patio with outdoor furniture plants and a mirror on the wall at The Studio in Bakewell
26
Bakewell, Peak District, DE45
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    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 £376

Last booked today
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A front garden with grass path and hedges in front of a stone house with white door and windows at Robin Cottage - 2 The Meadows in Darley Dale near Matlock
Offer
22
Darley Dale near Matlock, Derbyshire, DE4
  • Sleeps3
  • Bedrooms2
  • PetsYes

    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

  • £124 off - Sat 9th Aug to 16th Aug 2025

7 nights from £553

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A stone cottage with a tiled roof and red doors behind a stone wall at Number 5 Biggin near Hartington
15
Biggin near Hartington, Peak District, SK17
  • Sleeps3
  • Bedrooms2
  • PetsYes

    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

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Stone cottages with blue doors and flower pots along a narrow alley with greenery at Cutlers Cottage in Wirksworth
20
Wirksworth, Derbyshire, DE4
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    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 £332

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Exterior view of a row of stone houses with different colored doors and windows at Bobbin Cottage in Cromford near Matlock Bath
15
Cromford near Matlock Bath, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

Lovely romantic cottage with some wonderful features, including stone fireplace with woodburner. WiFi. A short walk to village amenities, making a perfect romantic break. Matlock 3 miles. (Ref. 923214)

  • Wi-fi

7 nights from £366

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Map View

 

Just Show Me Winster Cottages

Please find a selection of 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.