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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 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
    5.6 5 reviews
    5.6 5 reviews

    Accommodation at

    Mill Farm Cottages - Cherry Tree Cottage
    5
    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
    8.5 23 reviews
    8.5 23 reviews

    Accommodation at

  • 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
    8.6 5 reviews
    8.6 5 reviews

    Accommodation at

    Green Farm Holiday Cottages - The Pig Sty
    4
    2
    2
  • 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
    9.2 10 reviews
    9.2 10 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, near Chesterfield, Derbyshire
    Barlow, near Chesterfield, Derbyshire×

    The Barn at Woodland View

    Barlow, near Chesterfield, Derbyshire

    Barlow, near Chesterfield, Derbyshire

    4
    2
    1
    0
    Ref: UKC145
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Detached Property - Ground Floor Facilities
    Beautifully located in the small Derbyshire hamlet of Barlow, this stunning barn conversion provides an idyllic family retreat. Beautifully located in the small Derbyshire hamlet of Barlow, this stunning barn conversion provides an idyllic family retreat.
    Prices from
    8.7 7 reviews
    8.7 7 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
    9.9 28 reviews
    9.9 28 reviews

    Accommodation at

  • Markham Vale, near Chesterfield, Derbyshire
    Markham Vale, near Chesterfield, Derbyshire×
    Newly Listed
    The Stables

    The Stables

    Markham Vale, near Chesterfield, Derbyshire

    Markham Vale, near Chesterfield, Derbyshire

    4
    2
    2
    0
    Ref: UKC2684
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio
    The Stables holiday cottage, Markham Vale, with two comfortable en-suite bedrooms, is ideal for exploring Derbyshire and the Peak District. The Stables holiday cottage, Markham Vale, with two comfortable en-suite bedrooms, is ideal for exploring Derbyshire and the Peak District.
    Prices from
    10 1 reviews
    10 1 reviews

    Accommodation at

  • Holmesfield, near Dronfield, Derbyshire
    Holmesfield, near Dronfield, Derbyshire×
    Newly Listed
    The Stables

    The Stables

    Holmesfield, near Dronfield, Derbyshire

    Holmesfield, near Dronfield, Derbyshire

    4
    2
    1
    0
    Ref: UK4142
    Key Features:
    - Hot Tub - Luxury Property - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio
    Ideal for two couples or a family, this converted stable makes a welcoming retreat at any time of year, with many attractions within easy reach. Ideal for two couples or a family, this converted stable makes a welcoming retreat at any time of year, with many attractions within easy reach.
    Prices from
    0 0 reviews
    0 0 reviews

    Accommodation at

    Cowley Gore Cottages - The Coach House
    2
    1
    1
  • 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
    9.6 20 reviews
    9.6 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
    9.7 7 reviews
    9.7 7 reviews

    Accommodation at

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