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Chesterfield

Chesterfield’s history dates back to medieval times and is known for its famous crooked spire; but visitors will find a lot more to this town.

The first markets held in the town date back to around 1165 and they have been held here ever since, to become one of the biggest markets in the country.

The crooked spire at St. Mary’s and All Saints church is perhaps the town’s most renowned attraction and legend says it was bent by the Devil, but to be honest there’s probably more scientific explanations as to why it became crooked.

Further examples of Chesterfield’s history can be found at nearby Hardwick Hall Estate, a magnificent Elizabethan building with expansive gardens and a park. Or visit the fairy-tale style Bolsover Castle, which offers an audio-visual tour of the castle and on occasion even the chance to dress up as a cavalier! If that doesn’t quench your thirst for local knowledge then a visit to the Chesterfield Museum and Art Gallery is one of the best places to brush up on your local knowledge of the area.

Chesterfield has good shopping where you’ll find several high street names and of course the previously mentioned large open-air market and the lovely ‘Shambles’ area, which also features one of the UK’s oldest pubs.

If you’re ready to begin your exploration take a look at Chesterfield holiday cottages today.
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25 cottages are available
  • Holymoorside, near Chesterfield, Derbyshire
    Holymoorside, near Chesterfield, Derbyshire×

    Yew Tree Bothy

    Holymoorside, near Chesterfield, Derbyshire

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    1
    Ref: 26697
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Garden / Patio - Ground Floor Facilities - Woodburning Stove
    Yew Tree Bothy, which forms part of the owners’ home, provides small but comfortable holiday accommodation which...
    Prices from
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    Pets included
    Pets go free
  • Old Brampton, near Bakewell, Derbyshire
    Old Brampton, near Bakewell, Derbyshire×

    Priestfield Grange - Willow Cottage

    Old Brampton, near Bakewell, Derbyshire

    2
    1
    1
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    Ref: 13864
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Ground Floor Facilities - Rural Location
    Delightful adjoining holiday cottages with lattice French windows. Chestnut Cottage opening on to a south facing patio...
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    Pets included
    Pets go free
  • Barlow, near Chesterfield, Derbyshire
    Barlow, near Chesterfield, Derbyshire×

    Barlow Brook Cottage

    Barlow, near Chesterfield, Derbyshire

    2
    1
    1
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    Ref: RHHC
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Pub within 1 mile - Detached Property - Garden / Patio


    Barlow Brook Cottage is a gorgeous retreat for couples who want their own space away from the crowds, in the...

    Prices from
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    Pets included
    Pets go free
  • Barlow, Derbyshire
    Barlow, Derbyshire×

    The Stables

    Barlow, Derbyshire

    2
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    1
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    Ref: W42451
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Rural Location

    Countryside location

    This charming, terraced holiday cottage decorated with contemporary flair, adjoins...

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    Pets included
    Pets go free
  • Barlow near Bakewell, Derbyshire
    Barlow near Bakewell, Derbyshire×

    Mill Farm Cottage - Kingfisher Cottage

    Barlow near Bakewell, Derbyshire

    3
    1
    1
    1
    Ref: CC412042
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    These self catering cottages are situated in the beautiful Derbyshire village of Barlow, on the edge of the Peak...
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    Pets included
    Pets go free
  • Barlow near Bakewell, Derbyshire
    Barlow near Bakewell, Derbyshire×

    Mill Farm Cottages - The Nook

    Barlow near Bakewell, Derbyshire

    3
    1
    1
    1
    Ref: CC412039
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    These self catering cottages are situated in the beautiful Derbyshire village of Barlow, on the edge of the Peak...
    Prices from
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    Pets included
    Pets go free
  • Press, near Matlock, Derbyshire
    Press, near Matlock, Derbyshire×

    Bentley’s Barn

    Press, near Matlock, Derbyshire

    4
    2
    2
    1
    Ref: UK4087
    Key Features:
    - Hot Tub - Luxury Property - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Detached Property - Garden / Patio
    Bentley’s Barn is a great example of an idyllically placed barn conversion situated on the edge of the small village...
    Prices from
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    Pets included
    Pets go free
  • Cutthorpe, near Chesterfield, Derbyshire
    Cutthorpe, near Chesterfield, Derbyshire×

    Runner Duck Cottage

    Cutthorpe, near Chesterfield, Derbyshire

    4
    1
    1
    2
    Ref: UK4041
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Detached Property - Garden / Patio - Rural Location
    The fabulously named Runner Duck Cottage can be found surrounded by glorious Derbyshire countryside in a rural...
    Prices from
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    Pets included
    Pets go free
  • Clay Cross, near Chesterfield, Derbyshire
    Clay Cross, near Chesterfield, Derbyshire×

    The Old Dairy

    Clay Cross, near Chesterfield, Derbyshire

    4
    2
    2
    1
    Ref: 27381
    Key Features:
    - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Detached Property - Garden / Patio - Rural Location

    Set on the owners’ farm with far-reaching countryside views, this detached barn conversion offers modern...

    Prices from
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    Pets included
    Pets go free
  • Holmgate, near Chesterfield, Derbyshire
    Holmgate, near Chesterfield, Derbyshire×

    Ashmore Cottage

    Holmgate, near Chesterfield, Derbyshire

    4
    2
    1
    1
    Ref: 53
    Key Features:
    - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio - Rural Location

    This attractive 18th century stone cottage is situated between Clay Cross and Ashover. It has a garage and an...

    Prices from
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    Pets included
    Pets go free
  • Dore, near Sheffield, Derbyshire
    Dore, near Sheffield, Derbyshire×

    Pat’s Cottage

    Dore, near Sheffield, Derbyshire

    4
    2
    1
    1
    Ref: 30733
    Key Features:
    - Swimming pool - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio

    Pat’s Cottage is an attractive, 18th-century, semi-detached stone cottage, adjacent to the owners home, located...

    Prices from
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    Pets included
    Pets go free
  • Alton, near Matlock, Derbyshire
    Alton, near Matlock, Derbyshire×

    The Malt Shovel

    Alton, near Matlock, Derbyshire

    4
    2
    2
    1
    Ref: RV7
    Key Features:
    - Wifi - Car parking on site - Detached Property - Garden / Patio - Woodburning Stove

    This attractive detached barn has been thoughtfully converted retaining many beams and is situated in the grounds of...

    Prices from
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    Pets included
    Pets go free

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