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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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  • Barlow, Derbyshire
    Barlow, Derbyshire×

    The Stables

    Barlow, Derbyshire

    Barlow, Derbyshire

    2
    1
    1
    0
    Ref: W42451
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Rural Location
    A modern holiday cottage set in 17 acres of rolling countryside. Facilities to bring your own horse! A modern holiday cottage set in 17 acres of rolling countryside. Facilities to bring your own horse!
    Prices from
    8.9 10 reviews
    8.9 10 reviews

    Accommodation at

  • Barlow near Bakewell, Derbyshire
    Barlow near Bakewell, Derbyshire×

    Mill Farm Cottage - Kingfisher Cottage

    Barlow near Bakewell, Derbyshire

    Barlow near Bakewell, Derbyshire

    2
    1
    1
    1
    Ref: CC412042
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    Explore both the Peak District National Park and South Yorkshire from this cottage, which is one of four set within 50 acres of conservation pastures, woodland and lakes. Explore both the Peak District National Park and South Yorkshire from this cottage, which is one of four set within 50 acres of conservation pastures, woodland and lakes.
    Prices from
    4 3 reviews
    4 3 reviews

    Accommodation at

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • Cutthorpe, near Chesterfield, Derbyshire
    Cutthorpe, near Chesterfield, Derbyshire×
    Newly Listed
    Green Farm Cottages - The Old Cow Shed

    Green Farm Cottages - The Old Cow Shed

    Cutthorpe, near Chesterfield, Derbyshire

    Cutthorpe, near Chesterfield, Derbyshire

    2
    1
    1
    1
    Ref: UKC2608
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Rural Location
    This is an ideal choice for couples looking for a romantic break, close to the picturesque Peak District National Park. This is an ideal choice for couples looking for a romantic break, close to the picturesque Peak District National Park.
    Prices from
    8.7 9 reviews
    8.7 9 reviews

    Accommodation at

    Green Farm Holiday Cottages - The Pig Sty
    4
    2
    2
  • Holymoorside, near Chesterfield, Derbyshire
    Holymoorside, near Chesterfield, Derbyshire×

    Yew Tree Bothy

    Holymoorside, near Chesterfield, Derbyshire

    Holymoorside, near Chesterfield, Derbyshire

    2
    1
    1
    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 is only 3½ miles from Chesterfield, while Chatsworth House estate is nearby. Yew Tree Bothy is only 3½ miles from Chesterfield, while Chatsworth House estate is nearby.
    Prices from
    8.7 25 reviews
    8.7 25 reviews

    Accommodation at

  • Barlow, near Chesterfield, Derbyshire
    Barlow, near Chesterfield, Derbyshire×

    Barlow Brook Cottage

    Barlow, near Chesterfield, Derbyshire

    Barlow, near Chesterfield, Derbyshire

    2
    1
    1
    0
    Ref: RHHC
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Pub within 1 mile - Detached Property - Garden / Patio
    With floor-to-ceiling windows and a touch of charm and elegance, this romantic retreat for couples lies in tranquil surroundings. With floor-to-ceiling windows and a touch of charm and elegance, this romantic retreat for couples lies in tranquil surroundings.
    Prices from
    9.7 18 reviews
    9.7 18 reviews

    Accommodation at

  • Barlow near Bakewell, Derbyshire
    Barlow near Bakewell, Derbyshire×

    Mill Farm Cottages - The Nook

    Barlow near Bakewell, Derbyshire

    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
    One of four lovely cottages situated in the beautiful Derbyshire village of Barlow. Set in 50 acres of conservation pastures, lakeland and woodland. One of four lovely cottages situated in the beautiful Derbyshire village of Barlow. Set in 50 acres of conservation pastures, lakeland and woodland.
    Prices from
    0 0 reviews
    0 0 reviews

    Accommodation at

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • Barlow, Derbyshire
    Barlow, Derbyshire×

    The Cottage

    Barlow, Derbyshire

    Barlow, Derbyshire

    4
    2
    1
    0
    Ref: RCHP121
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio - Ground Floor Facilities - Rural Location
    Access to nearly 20 acres of open countryside on the edge of the National Park with French doors from both the lounge and bedroom giving way to beautiful views. Access to nearly 20 acres of open countryside on the edge of the National Park with French doors from both the lounge and bedroom giving way to beautiful views.
    Prices from
    9.4 17 reviews
    9.4 17 reviews

    Accommodation at

  • Scarcliffe, Chesterfield, Derbyshire
    Scarcliffe, Chesterfield, Derbyshire×

    The Old Coach House

    Scarcliffe, Chesterfield, Derbyshire

    Scarcliffe, Chesterfield, Derbyshire

    4
    1
    1
    0
    Ref: 26990
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Detached Property - Garden / Patio
    Scarcliffe is the ideal base, with walking, cycling, Hardwick Hall and Renishaw Hall and Gardens all easily accessible. Scarcliffe is the ideal base, with walking, cycling, Hardwick Hall and Renishaw Hall and Gardens all easily accessible.
    Prices from
    9.4 10 reviews
    9.4 10 reviews

    Accommodation at

  • Press, near Matlock, Derbyshire
    Press, near Matlock, Derbyshire×
    Newly Listed
    Bentley’s Barn

    Bentley’s Barn

    Press, near Matlock, Derbyshire

    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 - Ground Floor Facilities - Rural Location
    Bentley’s Barn really is the most fabulous holiday home situated in a peaceful and beautiful part of Derbyshire, complete with its own hot tub. Bentley’s Barn really is the most fabulous holiday home situated in a peaceful and beautiful part of Derbyshire, complete with its own hot tub.
    Prices from
    9.8 33 reviews
    9.8 33 reviews

    Accommodation at

  • Clay Cross, near Chesterfield, Derbyshire
    Clay Cross, near Chesterfield, Derbyshire×

    The Old Dairy

    Clay Cross, near Chesterfield, Derbyshire

    Clay Cross, near Chesterfield, Derbyshire

    4
    2
    2
    1
    Ref: 27381
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Detached Property - Garden / Patio - Rural Location
    Walks from the doorstep and coarse fishing close by, stabling for your horse available, helicopter rides locally. Walks from the doorstep and coarse fishing close by, stabling for your horse available, helicopter rides locally.
    Prices from
    9.7 20 reviews
    9.7 20 reviews

    Accommodation at

  • Cutthorpe, near Chesterfield, Derbyshire
    Cutthorpe, near Chesterfield, Derbyshire×

    Woodview Lodge

    Cutthorpe, near Chesterfield, Derbyshire

    Cutthorpe, near Chesterfield, Derbyshire

    4
    2
    1
    2
    Ref: UKC828
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Ground Floor Facilities
    Nestled in the heart of Derbyshire, this holiday property is the perfect base from which to explore the Peak District National Park. Nestled in the heart of Derbyshire, this holiday property is the perfect base from which to explore the Peak District National Park.
    Prices from
    9.6 5 reviews
    9.6 5 reviews

    Accommodation at

  • Alton, near Matlock, Derbyshire
    Alton, near Matlock, Derbyshire×

    The Malt Shovel

    Alton, near Matlock, Derbyshire

    Alton, near Matlock, Derbyshire

    4
    2
    2
    1
    Ref: RV7
    Key Features:
    - Wifi - Car parking on site - Detached Property - Garden / Patio - Woodburning Stove
    The Malt Shovel is a pet friendly barn conversion with lots of charm and character. Excellent walks from the door. The Malt Shovel is a pet friendly barn conversion with lots of charm and character. Excellent walks from the door.
    Prices from
    8.3 12 reviews
    8.3 12 reviews

    Accommodation at

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