Winster Cottages

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Winster Cottages

Your Winster, Derbyshire search returned 197 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
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
  • Pet FriendlyNo

    5.0★

    Perfect

  • 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 From £742

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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
  • Pet FriendlyNo

    4.8★

    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 From £372

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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
  • Pet FriendlyNo

    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 From £611

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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
  • Pet FriendlyNo

    4.8★

    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 From £605

Last booked yesterday
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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
  • Pet FriendlyNo

    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 From £441

Last booked yesterday
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A living room with sofas cushions a coffee table and a kitchen with black cabinets and a dining table with chairs at Number 4 Westmoreland in Two Dales
27
Two Dales, Derbyshire, DE4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

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

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights From £421

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Stone front exterior of a two story cottage with four windows two potted plants and a green door at Hill Cottage in Winster
Offer
26
Winster, Peak District, DE4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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

  • 20% off - Sat 27th Jun to 4th Jul 2026


for 7 nights From £602

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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
  • Pet FriendlyNo

    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 From £468

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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 & Derbyshire Dales, DE4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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 From £603

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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
  • Pet FriendlyNo

    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 From £702

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A stone house with a gravel driveway and flower beds surrounded by trees at Ivet Lowe in Hopton near Wirksworth
27
Hopton near Wirksworth, Derbyshire, DE4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

A classic semi-detached cottage resting in the quiet village of Hopton, close to Wirksworth, Derbyshire. Stone cottage. Multi-fuel burner. Carsington 0.3 miles; Wirksworth 2 miles; Brassington 3.9 miles. (Ref. 1012202)

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


for 7 nights From £479

Last booked yesterday
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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
  • Pet FriendlyNo

    4.8★

    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


for 7 nights From £420

Last booked yesterday
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A stone house with a tiled roof a patio area with a table and chairs and a lawn with trees at Ty Gambo in Oker near Matlock
48
Oker near Matlock, Derbyshire, DE4
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Ty Gambo is a holiday house resting in the village of Oker in Derbyshire. Hot tub. Woodburning stove. Smart TV. Off-road parking. In National Park. Matlock Bath 3.4 miles; Bakewell 9.6 miles. (Ref. 1142883)

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


for 7 nights From £1531

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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
  • Pet FriendlyNo

    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 From £570

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A stone house with a garden and paved paths leading to outdoor seating at Rose Cottage in Matlock
43
Matlock, Peak District & Derbyshire Dales, DE4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    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 From £732

Last booked yesterday
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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
  • Pet FriendlyNo

    4.9★

    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 From £1622

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A house with a stone exterior on a street at Belmont Cottage in Matlock
12
Matlock, Derbyshire, DE4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

Cottage in the Heart of Peak District is a wonderful cottage set in Middleton near Matlock, Derbyshire, offering open plan living and a Smart TV with Sky. Matlock Bath 3.5 miles; Bakewell 14.6 miles. (Ref. 1190900)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Sky TV


for 7 nights From £661

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A stone house with a gravel driveway and garden with flowers and trees at Dale View Farm in Dale End near Winster
31
Dale End near Winster, Peak District, DE45
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Warming barn conversion, Dale End near Winster in Derbyshire. Open-plan living area. Exposed beams. Countryside views. Winster 2 miles; Bakewell 7 miles; Matlock 7.1 miles. (Ref. 916808)

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


for 7 nights From £533

Last booked yesterday
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A stone cottage with whitewashed walls and brown framed windows next to a gravel yard with a white umbrella and plants at Hope Cottage in Youlgreave
32
Youlgreave, Peak District, DE45
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A delightful detached cottage resting in the heart of Youlgreave in the Peak District National Park. Woodburning stove. Exposed beams. Off-road parking. Rural. Bakewell 5 miles. (Ref. 1100132)

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


for 7 nights From £696

Last booked today
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An exterior view of a stone building with windows and door at The Coach House in Holloway
42
Holloway, Derbyshire, DE4
  • Sleeps7
  • Bedrooms3
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

The Coach House, a stunning, pet-friendly house nestled in the village of Holloway in Derbyshire, featuring a woodburning stove, and off-road parking. Matlock Bath 4.1 miles; Matlock 4.4 miles; Peak District National Park 9 miles. (Ref. 1161872)

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


for 7 nights From £825

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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.