by Wyndham Vacation Rentals
Shortlist

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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23 cottages are available
  • Barlow×

    The Stables

    Barlow

    2
    1
    1
    0
    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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  • Barlow, near Chesterfield×

    Barlow Brook Cottage

    Barlow, near Chesterfield

    2
    1
    1
    0
    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...

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  • Holymoorside, near Chesterfield×

    Yew Tree Bothy

    Holymoorside, near Chesterfield

    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, which forms part of the owners’ home, provides small but comfortable holiday accommodation which...
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  • Old Brampton, near Bakewell×

    Priestfield Grange - Willow Cottage

    Old Brampton, near Bakewell

    2
    1
    1
    1
    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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  • Barlow near Bakewell×

    Mill Farm Cottages - The Nook

    Barlow near Bakewell

    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...
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  • Barlow near Bakewell×
    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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  • Cutthorpe, near Chesterfield×

    Green Farm Holiday Cottages - The Pig Sty

    Cutthorpe, near Chesterfield

    4
    2
    2
    1
    Ref: W44184
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Rural Location - Woodburning Stove

    Tawny Owl Barn (ref 18220) and The Pig Sty (ref W44184) can be found in a sleepy village down a small country lane on...

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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 - 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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  • Holmgate, near Chesterfield×

    Ashmore Cottage

    Holmgate, near Chesterfield

    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...

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  • Cutthorpe, near Chesterfield×

    Woodview Lodge

    Cutthorpe, near Chesterfield

    4
    2
    1
    2
    Ref: UKC828
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Ground Floor Facilities

    This superb self-contained annexe is quietly attached to the owner’s home. Nestled in the sleepy village...

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  • Barlow×

    The Cottage

    Barlow

    4
    2
    1
    0
    Ref: RCHP121
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio - Ground Floor Facilities - Rural Location
    This beamed, single-storey, semi-detached cottage is set within 17 acres of open rolling countryside near the Peak...
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  • Cutthorpe, near Chesterfield×

    Runner Duck Cottage

    Cutthorpe, near Chesterfield

    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...
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Looking for something with a little more?

Cotages with Hot tubs Cottages part of our Luxury collection Something with a swimming pool A place near the Coast
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