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Popular Cottages
- 2-Bedroom House in Buxton
- 3-Bedroom Cottage in Ashover
- 2-Bedroom Apartment in Bakewell
- Dog-Friendly 2-Bedroom Cottage in Hayfield
- 2-Bedroom Cottage in Brassington
- 2-Bedroom Cottage with Log Burner in Baslow
- 2-Bedroom Barn in Blackwell
- 2-Bedroom Cottage with Log Burner in Ashbourne
- 1-Bedroom Barn in Bradbourne
- 1-Bedroom Barn in Pilsbury Near Buxton
- 1-Bedroom Barn in Snitterton
- 3-Bedroom Mill in Bakewell
- 2-Bedroom Cottage in Winster
- 1-Bedroom Cottage in Taddington
- Luxury 2-Bedroom Cottage in Ashford-in-the-Water
- 1-Bedroom Cottage in Ashover
- 1-Bedroom Cottage in Birchover
- 2-Bedroom Cottage in Hartington
- 3-Bedroom Barn with Parking in Eyam
- 3-Bedroom Cottage in Hackney
- 3-Bedroom Cottage with Log Burner in Blackwell
- 1-Bedroom Cottage with Log Burner in Bakewell
- 1-Bedroom House in Hope Valley
- 1-Bedroom Cottage in Ashford in the Water
- 2-Bedroom Cottage with Log Burner in Youlgrave
- 2-Bedroom Cottage with Parking in Buxton
- 2-Bedroom Barn in Bonsall
- 1-Bedroom House in Tansley
- 3-Bedroom Barn in Monyash
- 1-Bedroom Apartment in Foolow
Chesterfield Holiday Cottages
Rated Top 5 Most Popular Places in Derbyshire 2026 by our visitors
Our curated collection of Chesterfield 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 Chesterfield holiday home today.
- Edge of Peak District location
- 2 miles from Chesterfield
- Linacre Reservoirs on doorstep
- Near Chatsworth House
- Quiet residential setting
From £1,479 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.7
- Single-level studio for two
- Peak District National Park views
- Wood burner and enclosed garden
- Dog-friendly with onsite parking
- Walking distance to two pubs
From £334 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- 300 year old character cottage
- Peak District border location
- Two king-size en-suite bedrooms
- Working Aga and wood burner
- Direct access to countryside footpaths
From £611 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.8
- Stunning valley views from windows
- Stone barn for two guests
- Spacious garden with furnished patio
- Peak District walks from doorstep
- Near Chatsworth House and Chesterfield
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Stunning Peak District countryside views
- Two en-suite bedrooms sleep four
- Extensive gardens with Koi pond
- Exclusive summerhouse for guest use
- Near Chatsworth and Hardwick Hall
From £553 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
5
- Waterside garden with Barlow Brook
- Floor-to-ceiling windows throughout property
- Twenty minutes to Chatsworth House
- Modern kitchen with quartz worktops
- Peak District walks from doorstep
From £885 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Rustic Peak District barn conversion
- Two king-size bedrooms sleeping four
- Outdoor pizza oven and fire pit
- Free-standing bath in upstairs bedroom
- Wood burner and open-plan living
From £551 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Hand-built shepherd's hut for two
- Wood-fired pizza oven outdoors
- Illuminated ancient duck pond
- Peak District edge location
- Private parking for two cars
From £430 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Hilltop views across Derbyshire
- Wood burner and stone beams
- Enclosed garden with BBQ
- Freestanding bath and wet room
- Peak District on your doorstep
From £919 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.8
- Single-storey accessible layout throughout
- Sleeps 6 in three bedrooms
- Extensive gardens with countryside views
- 9 miles from Peak District
- One dog welcome at property
From £668 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Private hot tub with countryside views
- King-size bedroom with en-suite shower
- One dog welcome with enclosed garden
- Underfloor heating throughout property
- Walking distance to local pub
- Peak District location near Chatsworth
From £884 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.9
- Three bedrooms sleeping four guests
- Ground floor double bedroom available
- Furnished patio with BBQ area
- Two car parking spaces onsite
- Five miles from Peak District
From £684 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Stone cottage in Peak District
- Sleeps 4 with enclosed garden
- Dog-friendly welcomes 2 pets
- Near Chatsworth House 10 minutes
- South-facing patio with countryside views
From £534 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
5
- Romantic barn conversion for two
- Galleried king-size bedroom with views
- Original cruck beams and wood burner
- Walks start from the door
- Near Chatsworth and Haddon Hall
From £679 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- 38-acre farmland setting
- Far-reaching countryside views
- Two bedrooms sleeping four
- Family friendly rural retreat
- Close to Peak District attractions
From £454 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.5
- Stone cottage sleeping two guests
- King-size gallery bedroom with en-suite
- Elevated position with valley views
- Peak District walks from doorstep
- One dog welcome at property
From £498 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Stunning moorland views from terrace
- Secure fenced garden for dogs and kids
- Barn conversion near Chatsworth House
- Fire pit and BBQ on terrace
- Egyptian cotton bedding throughout
3-Bedroom Cottage in Bakewell
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- Sleeps 4 in 2 bedrooms
- Exposed beams and stone fireplace
- Three private parking spaces
- Secure bike storage included
- 1.5 miles from Ashover village
3-Bedroom Cottage in Bakewell
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- Two en-suite double bedrooms
- Private fields for dogs
- Mezzanine second lounge space
- Peak District walking routes nearby
- Parking for two cars
From £543 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Contemporary barn conversion sleeping three
- Two dogs welcome with field access
- Open-plan living with separate dining
- Peak District and Hardwick Hall nearby
- Parking for two cars included
From £531 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Sleeps 4 with valley views
- Wood burner and two lounges
- Freestanding bath and en-suite shower
- Wrap-around terrace with countryside outlook
- Near Chatsworth and walking trails
From £930 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.9
- Single-storey cottage sleeps four
- Three dogs welcome with enclosed garden
- Wood burner and contemporary kitchen
- Chatsworth House five miles away
- Peak District walks from doorstep
From £1,561 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Single-level bungalow sleeps six
- Large wood burner in lounge
- South-facing garden with countryside views
- Three bedrooms including one ensuite
- Five minutes from Matlock town
From £814 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Sleeps 2 in romantic barn conversion
- Welcomes two dogs with spacious grounds
- Stunning far-reaching countryside views throughout
- Country walks start from the property
- Close to Chatsworth House and Bakewell
From £484 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Set within Matlock Golf Club grounds
- Sleeps 5 across three bedrooms
- Enclosed secure garden for dogs
- Exclusive golf club discounts included
- 1.5 miles from Matlock town centre
From £572 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.9
- Wood-fired hot tub in courtyard
- Uninterrupted Derbyshire Dales views
- Woodland walk from the door
- Working farm with 3 bedrooms
- 2 miles from Matlock town
From £1,030 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Contemporary cottage near Matlock
- Two double bedrooms sleeping four
- Wood burner and Smart TV
- Two private patio areas
- Close to Chatsworth and Bakewell
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Working dairy farm with tours
- Wood burner and underfloor heating
- Two bedrooms sleeping four guests
- Countryside walks from the doorstep
- Two pubs within five minutes
From £567 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Stunning floor-to-ceiling countryside views
- Peaceful hilltop location near Matlock
- Sleeps 4 in two bedrooms
- Cosy wood-burner and spacious living
- Near Chatsworth House and Peak District
From £595 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Romantic cottage for two
- Dog-friendly with enclosed courtyard
- Walks to Lumsdale Falls
- Freestanding bath and wood burner
- Near Chatsworth and Bakewell
From £564 for 7 Nts
3-Bedroom Cottage in Bakewell
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Explore more of Derbyshire
Popular towns and villages in and around Chesterfield
Alfreton Ashbourne Bakewell Bamford Baslow Beeley Belper Bonsall Buxton Castleton 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