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Chesterfield Holiday Cottages

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.

Visitor Rating
Rating
4.9

Spire Haven

Hot Tub
Sleeps 8
Bedrooms: 4
  • Four bedrooms sleeping eight
  • Modern well-equipped kitchen
  • Enclosed garden with decking
  • Parking for three cars
  • Walk to Chesterfield centre
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Visitor Rating
Rating
4.9

Glenhurst

5 miles from Chesterfield
Hot Tub
Sleeps 10
Bedrooms: 5
  • Sleeps 10 across five bedrooms
  • Stunning Peak District valley views
  • Ground floor bedroom and facilities
  • Open plan living with woodburner
  • Ample parking for multiple cars
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Visitor Rating
Rating
4

Carpenter Cottage

5 miles from Chesterfield
Hot Tub
Sleeps 8
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Games room with pool table
  • Large garden with BBQ area
  • Parking for 3 cars included
  • 6 miles from Chatsworth House
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Visitor Rating
Rating
3.5

Hassop

6 miles from Chesterfield
Hot Tub
Sleeps 11
Bedrooms: 5
  • Sleeps 10 with lake access
  • Five bedrooms four bathrooms
  • Open plan group living space
  • Peak District location nearby
  • Ample parking multiple cars
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Visitor Rating
Rating
4.6

The Loft

6 miles from Chesterfield
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • Private hot tub and sauna
  • Bar billiards games room
  • Sleeps seven across three bedrooms
  • Four-car off-road parking
  • Two dogs welcome
  • Grade II listed character cottage
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Visitor Rating
Rating
4.7

The Old Robin Hood

6 miles from Chesterfield
Hot Tub
Sleeps 15
Pets 1
Bedrooms: 5
  • Sleeps 15 in Grade II listed house
  • Hot tub with countryside views
  • Games room with pool table
  • Five bedrooms, three bathrooms
  • Six miles from Chatsworth House
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Visitor Rating
Rating
5

Hallfield Hall

8 miles from Chesterfield
Hot Tub
Sleeps 14
Pets 1
Bedrooms: 6
  • Sleeps 14 with two hot tubs
  • Billiards room with bar area
  • Cinema and games rooms included
  • Six bedrooms with five bathrooms
  • Enclosed gardens with countryside views
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Visitor Rating
Rating
4.9

Oakwood House

8 miles from Chesterfield
Hot Tub
Sleeps 12
Pets 1
Bedrooms: 5
  • Five en-suite bedrooms sleep twelve
  • Ground floor bedrooms available
  • Smart TVs in every room
  • Two washing machines included
  • Five parking spaces provided
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Visitor Rating
Rating
4.9

Barncroft

8 miles from Chesterfield
Hot Tub
Sleeps 11
Pets 1
Bedrooms: 4
  • Hot tub with panoramic Peak District views
  • Sleeps 11 across four stylish bedrooms
  • Private parking for six cars available
  • Two woodburning stoves and underfloor heating
  • Ground floor bungalow near Matlock Bath
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Snowdrop Cottage

8 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • 50-jet hot tub with valley views
  • Games room with VW campervan bar
  • Five-tier gardens with tiki bar
  • Four double bedrooms sleep eight
  • Welcomes up to five dogs
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Visitor Rating
Rating
4.9

Arlington House

8 miles from Chesterfield
Hot Tub
Sleeps 16
Bedrooms: 8
  • Victorian townhouse sleeps 16
  • Games room with pool table
  • Private sauna in garden
  • Eight ensuite bedrooms available
  • Central Matlock Peak District location
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Visitor Rating
Rating
4.7

The Lillies

9 miles from Chesterfield
Hot Tub
Sleeps 12
Bedrooms: 5
  • Sleeps 12 in five bedrooms
  • Parking for five cars included
  • Peak District location near Chatsworth
  • Well-equipped kitchen seats everyone together
  • Steam railway 10 minutes walk
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Visitor Rating
Rating
4.4

Deeley House

9 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Four en-suite bedrooms available
  • Peak District National Park location
  • Parking for six cars provided
  • Georgian period house from 1874
  • Woodburning stove in sitting room
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Visitor Rating
Rating
4.6

Torestyn

9 miles from Chesterfield
Hot Tub
Sleeps 12
Bedrooms: 5
  • Sleeps 12 across five bedrooms
  • Four bathrooms including two full
  • Off-road parking for five cars
  • Large kitchen with dining area
  • Lawned garden with patio space
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Visitor Rating
Rating
4.7

Ty Gambo

9 miles from Chesterfield
Hot Tub
Sleeps 10
Bedrooms: 5
  • Sleeps 10 with hot tub
  • Five bedrooms, two bathrooms
  • Parking for 10 cars
  • One mile from Matlock Bath
  • Three ovens, modern kitchen facilities
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Visitor Rating
Rating
4

The Old Bulls Head

9 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Peak District village location
  • Multiple bedrooms and bathrooms
  • BBQ and outdoor furniture
  • WiFi throughout property
  • Walking trails from doorstep
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Visitor Rating
Rating
5

Aurora Matlock Bath

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 5
  • Five bedrooms sleeping eight
  • Modern kitchen with two ovens
  • Enclosed garden with patio
  • Wood burner in lounge
  • Walking distance to attractions
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Visitor Rating
Rating
4.6

Belgrano

10 miles from Chesterfield
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 5
  • Hot tub seating four people
  • Sleeps 10 across five bedrooms
  • Valley views over Matlock Bath
  • Walk to pubs and attractions
  • Victorian character with modern facilities
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Visitor Rating
Rating
4.6

Kirkham House

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Hot tub on south-facing terrace
  • Sleeps 8 across 4 bedrooms
  • Victorian character with modern facilities
  • 5 minutes walk to attractions
  • Wood burning stove and Sonos
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Visitor Rating
Rating
4.8

Blindwell House

10 miles from Chesterfield
Hot Tub
Sleeps 6
Pets 1
Bedrooms: 4
  • Four bedrooms sleeping seven
  • Open fire and garden
  • Peak District National Park location
  • Off-road parking included
  • Xbox and Smart TVs
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Sunnydene House

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Two cosy wood burners
  • Dog-friendly with enclosed courtyard
  • Near Chatsworth House and Bakewell
  • Private parking for multiple cars
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Visitor Rating
Rating
5

The Coach House

10 miles from Chesterfield
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • Three en-suite bedrooms
  • Sleeps seven guests
  • Peak District location
  • Modern renovated property
  • Wood-burning stove atmosphere
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Visitor Rating
Rating
4.7

Holloway House

10 miles from Chesterfield
Hot Tub
Sleeps 10
Bedrooms: 4
  • Sleeps 10 with parking for 4
  • Games room with pool table
  • Three bathrooms including two en-suites
  • Peak District views and walks
  • Large dining table seats 10 guests
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Visitor Rating
Rating
4.3

Querc

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Four bedrooms sleeps eight
  • Open-plan living space
  • Three bathrooms included
  • Private patio with barbecue
  • Peak District village location
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Riverside House Matlock Bath

10 miles from Chesterfield
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • Central Matlock Bath riverside location
  • Multiple bedrooms for larger groups
  • Walking distance to theme parks
  • Peak District National Park access
  • Traditional Victorian spa town setting
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Visitor Rating
Rating
4.1

The Mill Managers House

10 miles from Chesterfield
Hot Tub
Sleeps 14
Bedrooms: 7
  • Sleeps 14 in seven bedrooms
  • Grade I listed historic property
  • Large garden with children's trampoline
  • UNESCO World Heritage Site location
  • Walking distance to Cromford Mill
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Visitor Rating
Rating
4.3

Castle Hill

10 miles from Chesterfield
Hot Tub
Sleeps 8
Bedrooms: 4
  • Georgian townhouse sleeps eight
  • Open-plan group living space
  • Four flexible bedroom configurations
  • Central Bakewell walking distance
  • Peak District exploration base
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Visitor Rating
Rating
4.3

Roseville

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Hot tub with Black Rocks views
  • Sleeps 8 in 4 doubles
  • 18th-century beams and stonework
  • Central Cromford village location
  • Multiple outdoor terrace seating areas
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Visitor Rating
Rating
4.5

The Malthouse

10 miles from Chesterfield
Hot Tub
Sleeps 18
Bedrooms: 9
  • Grade II listed mill conversion
  • Sleeps eighteen across nine bedrooms
  • Three separate kitchen dining areas
  • Off road parking eight cars
  • Large garden with built-in BBQ
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Visitor Rating
Rating
4

Millbrook House

10 miles from Chesterfield
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Four bedrooms sleeps eight
  • Games room with table football
  • Waterside location beside brook
  • Five minute walk to town
  • Off-road parking three cars
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Unit 12, Bakewell Business Park, Ashford Road, Bakewell, Derbyshire, DE45 1EW