By Wyndham Vacation Rentals
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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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27 cottages are available
  • Old Brampton, near Bakewell×

    Priestfield Grange - Willow Cottage

    Old Brampton, near Bakewell

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    Ref: 13864
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Washing Machine - 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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  • Barlow, near Chesterfield×

    Barlow Brook Cottage

    Barlow, near Chesterfield

    2
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    Ref: RHHC
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Luxury Property - Detached Property - Garden / Patio - Dishwasher - Barbecue - No Pets Allowed


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

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  • Holymoorside, near Chesterfield×

    Yew Tree Bothy

    Holymoorside, near Chesterfield

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

    The Stables

    Barlow

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    Ref: W42451
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Dishwasher - Washing Machine - No Pets Allowed - Rural Location

    Countryside location

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

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

    Mill Farm Cottages - The Nook

    Barlow near Bakewell

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

    Ashmore Cottage

    Holmgate, near Chesterfield

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

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

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  • Barlow×
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    Ref: 27401
    Key Features:
    - Wifi - Pub within 1 mile - Washing Machine - Barbecue - No Pets Allowed - Rural Location

    Situated on the edge of The Peak District National Park these terraced stone barn conversions (refs 27400, 27401...

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  • Clay Cross, near Chesterfield×

    The Old Dairy

    Clay Cross, near Chesterfield

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

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

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  • Dronfield×
    4
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    Ref: 29766
    Key Features:
    - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Garden / Patio - Washing Machine - Barbecue - Rural Location

    Located in the Derbyshire village of Dronfield which lies between Sheffield and Chesterfield (both 7 miles), this...

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  • Alton, near Matlock×

    The Malt Shovel

    Alton, near Matlock

    4
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    2
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    Ref: RV7
    Key Features:
    - Wifi - Car parking on site - Detached Property - Garden / Patio - Dishwasher - Washing Machine

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

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  • Old Brampton, near Bakewell×

    Priestfield Grange - Chestnut Cottage

    Old Brampton, near Bakewell

    4
    2
    1
    2
    Ref: 11127
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Washing Machine - Ground Floor Facilities - Rural Location
    Delightful adjoining holiday cottages with lattice French windows. Chestnut Cottage opening on to a south facing patio...
    Discounted Price Today's Price
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