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 183 cottages

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Map View
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 £1449

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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★

    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 £445

Last booked 1 hour ago
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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

    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 £717

Last booked 2 days 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★

    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 £345

Last booked 2 days ago
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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 £431

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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
26
Winster, Peak District, DE4
  • 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

  • 20% off - Sat 20th Dec to 27th Dec 2025

  • 20% off - Sat 27th Dec 2025 to 3rd Jan 2026


for 7 nights £519

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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 £516

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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
  • 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 £699

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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 £702

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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

    4.9★

    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 £1597

Last booked 2 days ago
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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
  • PetsNo

    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 £1349

Last booked yesterday
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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 £471

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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★

    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 £410

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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 £470

Last booked today
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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 £501

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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
  • PetsYes

    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)

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


for 7 nights £533

Last booked 3 hours 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 £606

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Front view of a stone building with a black door and windows behind trees and a gate at Winster Hall in Winster
59
Winster, Peak District & Derbyshire Dales, DE4
  • Sleeps16
  • Bedrooms7
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A magnificent 17th century country house set in the centre of Winster, ideal for family and friends with lovely formal gardens and a summerhouse. (Ref. 30946)

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


for 7 nights £2311

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A stone house with white door and windows garden area with hot tub and plants at Woodbine Cottage in Winster
20
Winster, Peak District, DE4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This charming detached house rests within the Peak District National Park in Wensley near Winster, Derbyshire. Enclosed garden. WiFi. Smart TV. Gas Fire. Winster 1.5 miles; Matlock 3.7 miles; Bakewell 7.2 miles. (Ref. 1077706)

  • Wi-fi
  • Hot Tub
  • Dishwasher

  • 10% off - Fri 5th Dec to 12th Dec 2025

  • 10% off - Fri 12th Dec to 19th Dec 2025


for 7 nights £482

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A stone building with a dark door and windows along a sidewalk at Dragon Hill Barn Brassington
31
Brassington, Peak District & Derbyshire Dales, 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 £436

Last booked 9 hours ago
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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.