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Popular Cottages
- Pinster
- Apartment 5 The Castleton Suite
- Rutland Mews
- Campion Cottage Peak
- Fair View Barn
- Pipistrelle Barn
- Dairy Croft
- Griffedale
- Bilberry Barn
- Henmore Grange Cottage
- Tigh An Chuain
- Olives Place
- Golconda Cottage
- Cara
- The Old Wash House
- Snelslow Barn
- Wash House Cottage
- Blakelow Barn
- Spinners Cottage
- Spring Barn East
- The Old Chapel
- Hillcrest Barn
- The Hay Loft Turnditch
- Badger Cottage
- Black Spout Cottage
- Limestone House
- Orrs Barn
- Valley Cottage
- Harebell Hill
- The Cottage Elton
Winster Holiday Cottages
Rated Top 5 Most Popular Places in Derbyshire 2026 by our visitors
Our curated collection of Winster cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Winster holiday home today.
Visitor Rating
4
- Grade II listed 300-year-old cottage
- Woodburner in gritstone fireplace
- Walking distance to village amenities
- Garden with study room access
- Peak District location near Matlock
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Visitor Rating
4
- Single-level cottage for two
- Mature gardens with rolling views
- Peak District walking routes nearby
- En-suite bedroom with garden outlook
- Enclosed courtyard with outdoor seating
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Visitor Rating
4.6
- Panoramic Peak District countryside views
- Converted stone barn sleeping two
- Welcome up to three dogs
- Enclosed patio with outdoor dining
- Walking distance to local pub
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Visitor Rating
4.8
- Kinder Scout walks from door
- Wood burner and two sitting rooms
- King-size bedroom with en-suite shower
- Enclosed garden with Peak views
- Village location with pubs nearby
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Visitor Rating
4
- Direct access to Kinder Scout trails
- Stone cottage sleeping three guests
- Open fire in lounge area
- Elevated garden with countryside views
- Two dogs welcome throughout cottage
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Visitor Rating
3
- Adjacent to Kinder Scout path
- Spectacular Dark Peak views everywhere
- Wood burner in beamed lounge
- Sleeps four in two bedrooms
- Dog friendly walking paradise
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- Four-storey townhouse sleeping six to eight
- Two dogs welcome with Peak walks
- Modern kitchen with dishwasher and utility
- Two separate living rooms across floors
- Near Bugsworth Basin and Lyme Park
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating and wood burner
- Walks directly from the door
- Welcomes up to three dogs
- Peaceful end-of-lane converted coach house
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating throughout
- Wood burner and leather seating
- Welcomes up to 3 dogs
- Peak District countryside location
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Visitor Rating
4.6
- Part of Georgian mansion grounds
- Wood burner and flagstone floors
- Welcomes three dogs
- Extensive woodland walking routes
- Double with Juliet balcony views
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Visitor Rating
4
- 18th-century barn with countryside views
- Two en-suite bedrooms sleeping four
- Kitchen garden with organic produce
- Wood pellet heating and underfloor warmth
- Walking and cycling from doorstep
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Visitor Rating
4
- Upside-down cottage with valley views
- Log burning stove and cosy sofas
- Walks from door across Peak moorland
- Two bathrooms including walk-in shower
- Sleeps four with two ground bedrooms
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Visitor Rating
4
- Woodland setting with babbling stream
- Sleeps 4 in 2 bedrooms
- Wood burner and vaulted ceilings
- Kinder Scout on the doorstep
- Welcomes 2 dogs with parking
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Visitor Rating
4
- Ground-floor barn conversion for two
- Welcomes two dogs to Peak District
- Floor-to-ceiling windows with tree views
- King-size bedroom with shower room
- Shared gardens with BBQ and stream
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Visitor Rating
4
- Woodburner with logs provided
- Adjacent village pub dining
- Hillside walks from doorstep
- Two dogs welcome
- Countryside views from bedroom
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Visitor Rating
4
- Sleeps 2 on working farm
- Wood burner with logs included
- Two bathrooms off bedroom
- Mountain bike secure storage
- Stunning Peak District countryside views
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Visitor Rating
4.4
- Former bakery with original features
- Sleeps 4 in two bedrooms
- Three-tiered garden with summer house
- Mam Tor views from top tier
- Central Castleton village location
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Visitor Rating
4
- Walks directly from the cottage door
- Wood burner in stone fireplace
- Hope railway station in village
- Secluded courtyard garden with seating
- Recently renovated throughout
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Visitor Rating
4
- Sleeps 6 in Hope Valley
- Two dogs welcome with garden
- Three bedrooms in characterful cottage
- Walking distance to Hope village
- Pennine Way on the doorstep
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Visitor Rating
4
- Converted barn under Winn Hill
- Sleeps four with two bedrooms
- Two dogs welcome with gardens
- Hope Valley views from living space
- Half mile to Hope train station
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- Converted barn with original features
- Sleeps 2 in mezzanine bedroom
- Free-standing bath and walk-in shower
- Peak District National Park location
- Walking trails from your door
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Visitor Rating
3
- Sleeps 2 with 2 dogs welcome
- South-facing garden with BBQ facilities
- Single-level accessible cottage layout
- Pennine Way walks from doorstep
- Peaceful courtyard in Hope Valley
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Visitor Rating
4
- Sleeps 6 in Peak District
- Two dogs welcome
- Open coal fire in lounge
- Two en-suite double bedrooms
- Separate snug with TV and games
- Near Pennine Way and Ladybower Reservoir
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Visitor Rating
5
- King-size bedroom sleeps two
- Half mile from Buxton centre
- Peak District walking on doorstep
- Smart TV and dining area
- Onsite parking included
- Spotlessly clean throughout
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Visitor Rating
4
- Private parking for two cars
- Three bedrooms sleeping five guests
- Walk to Buxton town centre
- Peak District footpaths on doorstep
- Modern kitchen with range cooker
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Visitor Rating
4.8
- First-floor Georgian apartment, sleeps two
- Central Buxton, walk to everything
- Modernised 2024 with original artwork
- King-size bed and walk-in shower
- Parking permit and Peak District access
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- Two wood burners throughout
- Cinema screen with surround sound
- Private tiered garden with deck
- Sleeps 6-8 guests comfortably
- Three dogs welcome
- Walking distance to Buxton centre
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- On edge of Pavilion Gardens
- Sleeps 5 across 3 bedrooms
- Master bedroom with en-suite bathroom
- Onsite parking in central Buxton
- Welcomes up to 2 dogs
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- Beside Pavilion Gardens Buxton
- Sleeps six across three bedrooms
- Two bathrooms including ensuite
- Town centre with onsite parking
- Welcomes two dogs
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- Grade II-listed mansion apartment
- Overlooks 23-acre Pavilion Gardens
- Two bedrooms sleeping four guests
- Underfloor heating throughout property
- One mile from Pool's Cavern
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Explore more of Derbyshire
Popular towns and villages in and around Winster
Alfreton Ashbourne Bakewell Bamford Baslow Beeley Belper Bonsall Buxton Chatsworth Chellaston Chelmorton Chesterfield Chinley Clay Cross Cromford Darley Dale Denby Dronfield Edale Eyam Glossop Hadfield Hartington Hathersage Hayfield Heath Holmesfield Hulland Ward Kirk Ireton Kirk Langley Matlock Matlock Bath Over Haddon Somercotes South Wingfield Tansley Tideswell Tissington Whaley Bridge Wirksworth Youlgreave