Winster Cottages

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Winster Cottages

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Your Winster, Derbyshire search returned 186 cottages

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Map View
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★

    Outstanding

  • 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


for 7 nights $607

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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★

    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


for 7 nights $494

Last booked yesterday
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A house with a stone wall hedge and white gate with woodlands sign at Woodlands in Darley Dale
40
Darley Dale, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

An attractive dormer bungalow resting in Darley Dale, close to the Peak District National Park. Close to amenities. Off-road parking. Wheelchair friendly. Matlock 3.1 miles; Bakewell 5.5 miles; Ashbourne 15.4 miles. (Ref. 1077976)

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


for 7 nights $747

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A stone house with a garden and paved paths leading to outdoor seating at Rose Cottage in Matlock
43
Matlock, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Rose Cottage is a charming, stone-built cottage settled into the bustling town of Matlock, Derbyshire. Close to National Park. Near shop, pub, and river. Matlock Bath 1.8 miles; Peak District National Park 5 miles, Bakewell 8.7 miles. (Ref. 958573)

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


for 7 nights $983

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A single story house with a stone wall and a garage door at Rozel in Youlgreave
40
Youlgreave, Peak District, DE45
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A light and airy dorma bungalow surrounded by stunning countryside in the historic village of Youlgreave. Spacious interior. Ideal for walkers. Bakewell 3 miles. (Ref. 1039868)

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


for 7 nights $974

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Stone exterior of a two story house with windows and a grey door labeled church cottage in Bakewell
36
Bakewell, Peak District, DE45
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

This gorgeous three-storey cottage lies in Bakewell, Derbyshire. Enclosed garden. No pets. Bedroom with en-suite. Off-road parking. Chatsworth 9.6 miles; Matlock 8.3 miles; Buxton 12.3 miles. (Ref. 1064674)

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


for 7 nights $1128

Last booked 6 hours ago
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The front of a stone house with a blue door and decorative windows at Arlington House in Matlock
42
Matlock, Derbyshire, DE4
  • Sleeps16
  • Bedrooms8
  • PetsNo

    4.8★

    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 $2104

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A stone house with wooden doors and windows and a patio with a bench and plants at Rowtor in Birchover
49
Birchover, Peak District, DE4
  • Sleeps9
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Rowtor is a wonderfully-adorned barn conversion residing in Birchover near Winster, Derbyshire. In the Peak District National Park. Study. Mezzanine study. Ground-floor bedrooms and open-plan living. Character. Bakewell 5.6 miles; Matlock 6.3 miles. (Ref. 1120844)

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


for 7 nights $983

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A stone building with a wooden fence and gate near a grassy slope at Horsedale Barn in Bonsall
19
Bonsall, Peak District, DE4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Horsedale Barn is a charming farm stay ideal for couples, nestled in the village of Bonsall in Derbyshire, on the edge of the Peak District National Park. Matlock Bath 3.6 miles; Matlock 4.6 miles; Bakewell 9.9 miles. (Ref. 1161151)

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


for 7 nights $623

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A stone building with slate roof and wooden door surrounded by plants at Grove Farm Barn in Darley Dale
29
Darley Dale, Derbyshire, DE4
  • Sleeps3
  • 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


for 7 nights $667

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A stone and plaster cottage with chimneys on a paved road at Bedehouse Cottage in Cromford near Matlock Bath
27
Cromford near Matlock Bath, Derbyshire, DE4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A lovely, character cottage in the World Heritage village of Cromford. WiFi. Beams, stone walls and a patio garden with furniture. Wonderful base for exploring the Derbyshire Dales. Matlock 3 miles. (Ref. 903532)

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


for 7 nights $664

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An outdoor deck with a hot tub and wicker sofa overlooking a village and green hills at Barncroft in Tansley near Matlock
45
Tansley near Matlock, Derbyshire, DE4
  • Sleeps11
  • Bedrooms4
  • PetsYes

    5.0★

    Perfect

  • 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


for 7 nights $1917

Last booked 6 hours ago
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Stone building with two windows and a door with ivy and outdoor table and chairs at Cambridge Lodge in Wensley near Matlock
46
Wensley near Matlock, Peak District, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Outstanding, unique converted water tank. Rurally located with amazing views that reach Chatsworth House. Open plan living, character features. Wonderful base for the Peak District. Bakewell 8 miles. (Ref. 903901)

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


for 7 nights $865

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Stone house with red door and red mailbox with potted plants outside near a tree with pink blossoms at Richfield in Winster
43
Winster, Peak District, DE4
  • 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


for 7 nights $1009

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A stone building with a dark door and windows along a sidewalk at Dragon Hill Barn Brassington
31
Brassington, Derbyshire, DE4
  • 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


for 7 nights $607

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Stone cottage with yellow door and blue metal benches outside at 1 Barley Cottages in Matlock
51
Matlock, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A fabulous, three-bedroom home resting in Matlock, Derbyshire. Countryside views. Near National Park. Close to amenities and attractions. Woodburning stove. Stylish. Matlock Bath 2.5 miles; Bakewell 9.3 miles. (Ref. 1118940)

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

  • 10% off - Mon 29th Dec 2025 to 2nd Jan 2026

  • $482 off - Fri 2nd Jan to 9th Jan 2026


for 7 nights $773

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A stone cottage exterior with white windows a grey door and a stone wall with plants at Daisy Cottage in Winster
33
Winster, Peak District, DE4
  • 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
  • Dishwasher
  • Baby-friendly


for 7 nights $612

Last booked yesterday
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A front garden with green plants and purple flowers in front of a stone house with white framed windows at Cloudberry Cottage in Birchover
27
Birchover, Peak District, DE4
  • 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


for 7 nights $571

Last booked 2 days ago
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A stone patio with a wooden picnic table and benches with cushions and sunflowers on the table in front of a stone building with large windows and a lawn at Brightside in Birchover
32
Birchover, Peak District, DE4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

This superbly-renovated former barn is perched in Winster, Derbyshire. In a National Park. Off-road parking. Ground-floor living. EV charging. Open-plan. Bakewell 5.6 miles; Matlock 6.3 miles. (Ref. 1120845)

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


for 7 nights $868

Last booked today
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Exterior view of a stone cottage with a white door and window and a small white table and chairs outside at Stable Cottage in Cromford
30
Cromford, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A delightful stone-built cottage nestled in Cromford, Derbyshire. Open-plan. Woodburning stove. Pet-friendly. Matlock 2.5 miles. (Ref. 1062326)

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


for 7 nights $660

Last booked yesterday
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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.