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- Northwood Farm The Granary
- The Old Shop
- Springdale House
- Archstones
- Fox House
- Millbrook House
- Stonecroft
- Hassop
- Sunnydene House
- Torestyn
- Talbot House
- Pippinwell
- 2 Carr Farm Close
- Heathylee
- The Edge
- 11 Eagle Parade
- The Rooftop
- The Farmhouse
- Cheshire House
- The Old Cowsheds
- Fold Yards at Rowan Cottage
- Our Spring Cottage
- Heron House
- Queen Ann's Close
- Holloway House
- Bagshot House
- The Barn at Hill House
- The Farmhouse
- Querc
- Damson & Orchard
Winster Holiday Cottages
Rated Top 5 Most Popular Places in Peak District 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
4.9
- Sleeps 8 in 4 bedrooms
- Oak lodge summer house
- 80-inch TV main lounge
- Three-car designated parking
- Peak District gateway location
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Visitor Rating
4.9
- Six bedrooms sleep twelve
- Games room with table tennis
- Five car parking spaces
- Peak District location nearby
- Multiple bathrooms and living areas
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Visitor Rating
4.9
- Hot tub for six people
- Three separate living spaces available
- Sleeps 12 across five bedrooms
- Four bathrooms, no morning queues
- Walking distance to Glossop town
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Visitor Rating
4.9
- Sleeps 8 with private hot tub
- Four bedrooms with memory foam beds
- Three living areas including conservatory
- Fully equipped kitchen with dishwasher
- Walking distance to Glossop centre
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- Hot tub with countryside views
- Sleeps 8 across 4 bedrooms
- Three cars private parking
- Wood burner and enclosed gardens
- Peak District walks from doorstep
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Visitor Rating
4.8
- Sleeps 14 with hot tub
- Games room with pool table
- Six bedrooms, five bathrooms
- Bar area and outdoor cooking
- Near Peak District National Park
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Visitor Rating
4.8
- Sleeps ten guests comfortably
- Canal-side marina location setting
- Four bedrooms three bathrooms
- Open-plan living dining kitchen
- Peak District hiking base
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Visitor Rating
4.8
- Cricket field views
- Stone built character
- Sleeps 8 guests
- Open fire living room
- Peak District location
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Visitor Rating
4.9
- Riverside location with river views
- Four bedrooms sleeping eight guests
- Village centre with local amenities
- Woodburning stove and Smart TV
- Walking access to Kinder Scout
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Visitor Rating
4.7
- Sleeps 8 across 4 bedrooms
- Two separate sitting rooms
- Enclosed garden with patio
- Off-road parking for 2
- Peak District National Park edge
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Visitor Rating
4
- Working farm with animals
- Four bedrooms sleep eight
- Large farmhouse kitchen table
- Peak District walks from doorstep
- Ample off-road parking space
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Visitor Rating
4
- Working farm setting
- Games room pool table
- Sleeps 8 guests comfortably
- Dining seats 12 people
- Peak District countryside views
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Visitor Rating
4.4
- Sleeps 16 across 6 bedrooms
- Parking for 6 cars
- Extensive gardens for groups
- Wood-burning stove and fires
- Peak District countryside location
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Visitor Rating
4.7
- Four double bedrooms sleep eight
- Games room with pool table
- Four bathrooms including two en-suites
- Peak District walking from doorstep
- Electric vehicle charging point available
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- Two lodges sleeping 12 guests
- Peak District National Park edge
- Walking distance to village centre
- Six bedrooms across both properties
- Close to Buxton and Castleton
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Visitor Rating
4.6
- Sleeps 12 across six bedrooms
- Hot tub on rear decking
- Full-size snooker table included
- Parking for three cars
- Four dogs welcome
- Victorian character features throughout
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Visitor Rating
4
- Four en-suite bedrooms
- Working farm setting
- Direct Peak District walks
- Ground floor accessibility
- Fully equipped group kitchen
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Visitor Rating
4.4
- Historic 12th century Norman mansion
- Sleeps 16 across seven bedrooms
- Games room with snooker table
- 1.5 acres gardens plus woodland
- Peak District walking from doorstep
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Visitor Rating
4.1
- Hot tub in enclosed courtyard
- Sleeps eight across four bedrooms
- Two en-suite bedrooms with showers
- Central Castleton village location
- Walking distance to caves and pubs
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Visitor Rating
4.9
- Four bedrooms sleep eight
- Central Castleton village location
- Three car parking spaces
- Open-plan kitchen dining area
- Four bathrooms including en-suites
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Visitor Rating
4.8
- Games room with pool table
- Four bedrooms sleeping seven guests
- Woodburning stove in sitting room
- Five minutes walk to Peveril Castle
- Central Castleton village location
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Visitor Rating
4.8
- Grade 2 listed cottage
- Sleeps 8 across 4 bedrooms
- Contemporary kitchen with granite worktops
- Spacious living dining room
- Enclosed garden with patio
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- Sleeps 8 with 4 en-suites
- Parking for 4 cars included
- Two terraces with Peak views
- Hope Valley Peak District location
- Dog-friendly welcomes 3 pets
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- Peak District National Park location
- Multiple bedrooms for group stays
- Walking trails from the doorstep
- Near Castleton and Chatsworth House
- Private parking for several vehicles
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Visitor Rating
4.7
- Sleeps 8 in 4 bedrooms
- Two downstairs double bedrooms
- Near Ladybower Reservoir walks
- Three pets welcome
- Peak District village location
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Visitor Rating
5
- Sleeps 12 across five bedrooms
- Games room for group entertainment
- Four bathroom facilities throughout
- Off-road parking four cars
- Peak District National Park location
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Visitor Rating
4.6
- Sleeps 8 in family bedrooms
- Underfloor heating throughout
- Pet-friendly meadow setting
- Near Castleton caves
- Off-road parking included
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Visitor Rating
4.8
- Rooftop hot tub with LED lighting
- Two separate living areas for groups
- Three bathrooms including two en-suites
- Central Buxton location near station
- Sleeps eight across four bedrooms
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Visitor Rating
4.7
- Sleeps 12 guests comfortably
- Cinema room for group entertainment
- Central Buxton spa town location
- Off-road parking three cars
- Opera House garden views
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Visitor Rating
4
- Sleeps 18 in nine bedrooms
- Cinema room with football table
- Seven bathrooms, most en-suite
- Five minutes walk to Buxton centre
- Parking for four cars on-site
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Popular towns and villages in and around Winster