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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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  • 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
    8.8 12 reviews
    8.8 12 reviews

    Accommodation at

    Green Farm Holiday Cottages - Tawny Owl Barn
    5
    3
    3
  • 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 2 reviews
    4 2 reviews

    Accommodation at

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • 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
    9.6 20 reviews
    9.6 20 reviews

    Accommodation at

  • 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
    8.6 10 reviews
    8.6 10 reviews

    Accommodation at

  • 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
    8.6 25 reviews
    8.6 25 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
  • 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 32 reviews
    9.8 32 reviews

    Accommodation at

  • Temple Normanton, near Chesterfield, Derbyshire
    Temple Normanton, near Chesterfield, Derbyshire×

    Lings Farm Cottage

    Temple Normanton, near Chesterfield, Derbyshire

    Temple Normanton, near Chesterfield, Derbyshire

    4
    2
    1
    0
    Ref: UKC2347
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio - Woodburning Stove
    Explore the beautiful Peak District National Park from this cottage, with Haddon Hall, Chatsworth House and Bakewell all close by. Explore the beautiful Peak District National Park from this cottage, with Haddon Hall, Chatsworth House and Bakewell all close by.
    Prices from
    9.5 6 reviews
    9.5 6 reviews

    Accommodation at

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

    Green Farm Holiday Cottages - The Pig Sty

    Cutthorpe, near Chesterfield, Derbyshire

    Cutthorpe, near Chesterfield, Derbyshire

    4
    2
    2
    1
    Ref: W44184
    Key Features:
    - Hot Tub - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Garden / Patio - Rural Location - Woodburning Stove
    Beautifully located with many walking trails nearby to explore and attractions to discover, a perfect family holiday home. Beautifully located with many walking trails nearby to explore and attractions to discover, a perfect family holiday home.
    Prices from
    9.1 27 reviews
    9.1 27 reviews

    Accommodation at

    Green Farm Holiday Cottages - Tawny Owl Barn
    5
    3
    3
  • Tibshelf, near Alfreton, Derbyshire
    Tibshelf, near Alfreton, Derbyshire×

    Hunters Cottage

    Tibshelf, near Alfreton, Derbyshire

    Tibshelf, near Alfreton, Derbyshire

    4
    2
    2
    0
    Ref: UK4069
    Key Features:
    - Hot Tub - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio - Woodburning Stove - Baby and Toddler Friendly
    This property is a must for a family or small group of friends looking for a perfect base from which to explore the magnificent Peak District and Nottinghamshire. This property is a must for a family or small group of friends looking for a perfect base from which to explore the magnificent Peak District and Nottinghamshire.
    Prices from
    9.2 6 reviews
    9.2 6 reviews

    Accommodation at

  • Holmgate, near Chesterfield, Derbyshire
    Holmgate, near Chesterfield, Derbyshire×

    Ashmore Cottage

    Holmgate, near Chesterfield, Derbyshire

    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
    A traditional stone built property located between Clay Cross and Ashover. Good for accessing both the Peak District National Park, Bakewell and Matlock. A traditional stone built property located between Clay Cross and Ashover. Good for accessing both the Peak District National Park, Bakewell and Matlock.
    Prices from
    9.5 8 reviews
    9.5 8 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

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