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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

    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
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    Pets included
    Pets go free

    Accommodation at

    Countryside location

    This charming, terraced holiday cottage decorated with contemporary flair, adjoins the owner’s property set in 17 acres of rolling countryside near the Peak District National Park. The spa town of Buxton, Bakewell and the caves around Castleton are all only a short drive away, as is the famous Chatsworth Estate with its many attractions. Visit the Heights of Abraham by cable car in Matlock Bath or walk part of the famous Pennine Way in the High Peak. For...

  • Holymoorside, near Chesterfield, Derbyshire
    Holymoorside, near Chesterfield, Derbyshire×

    Yew Tree Bothy

    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
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    Pets included
    Pets go free

    Accommodation at

    Yew Tree Bothy, which forms part of the owners’ home, provides small but comfortable holiday accommodation which is ideally located on the edge of the Peak District National Park. Surrounded by 30 acres of land, the property has its own sitting-out area from which to enjoy the peace and tranquillity of the surrounding area. The village of Holymoorside has 2 pubs, 3 churches and a small local shop; a wider range of amenities can be found in Chesterfield which is 3½ miles away....
  • Barlow, near Chesterfield, Derbyshire
    Barlow, near Chesterfield, Derbyshire×

    Barlow Brook Cottage

    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
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    Pets included
    Pets go free

    Accommodation at


    Barlow Brook Cottage is a gorgeous retreat for couples who want their own space away from the crowds, in the heart of the beautiful Derbyshire countryside. This detached, tranquil cottage sits in an Area of Outstanding Natural Beauty and lies adjacent to the owners’ home. It is completely self-contained with its own private driveway, allowing you to relax in peaceful surroundings in considerable comfort. The welcoming owners have done everything possible to combine many...

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

    Mill Farm Cottages - The Nook

    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.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    These self catering cottages are situated in the beautiful Derbyshire village of Barlow, on the edge of the Peak District National Park and close to the South Yorkshire border, Mill Farm provides a superb base for both holiday breaks. fishing holidays and business visits. The four cottages are close to the village and set in 50 acres of conservation pastures. lakes and woodland teeming with fish, birds and wildlife.

    Ground Floor: Property is all at ground floor level, has gas central...

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

    Mill Farm Cottage - Kingfisher Cottage

    Barlow near Bakewell, Derbyshire

    3
    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    These self catering cottages are situated in the beautiful Derbyshire village of Barlow, on the edge of the Peak District National Park and close to the South Yorkshire border, Mill Farm provides a superb base for both holiday breaks. fishing holidays and business visits. The four cottages are close to the village and set in 50 acres of conservation pastures. lakes and woodland teeming with fish, birds and wildlife.

    Ground Floor: Property has gas fire and electric heaters and comprises:...

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • Cutthorpe, near Chesterfield, Derbyshire
    Cutthorpe, near Chesterfield, Derbyshire×

    Green Farm Holiday Cottages - The Pig Sty

    Cutthorpe, near Chesterfield, Derbyshire

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

    Accommodation at

    Tawny Owl Barn (ref 18220) and The Pig Sty (ref W44184) can be found in a sleepy village down a small country lane on the owner’s non working farm. As former barns they have been sympathetically converted retaining many beautiful features such as exposed beams and exposed stone walls. They each boast a hot tub (at cost), and for that added sense of relaxation, dressing gowns, towels and slippers are provided within the cost. Just 10 minutes outside the Peak District National Park,...

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

    Woodview Lodge

    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    This superb self-contained annexe is quietly attached to the owner’s home. Nestled in the sleepy village of Cutthorpe, in the heart of Derbyshire, you can explore the Peak District National Park within a few minutes drive. With open countryside views to the front and beautiful fields to the rear, Cutthorpe village is semi-rural and home to the fabulous Linacre Reservoirs, which are surrounded by fields and bluebell woods which provide many walking trails for all abilities....

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

    The Old Coach House

    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    This former coach house is set within the peaceful and historic village of Scarcliffe. Standing detached, the accommodation offers the perfect holiday base for walking, cycling, shopping at Meadow Hall, McArthur Glen or visiting one of the many attractions this area has to offer. Hardwick Hall, Bolsover Castle, Renishaw Hall and Gardens (a treasure trove for art lovers), Creswell Crags for the caves and events, the Rother Valley offering water sports, golf and activity park are all...

  • Alton, near Chesterfield, Derbyshire
    Alton, near Chesterfield, Derbyshire×
    Newly Listed
    The Old Church

    The Old Church

    Alton, near Chesterfield, Derbyshire

    4
    2
    3
    0
    Ref: UKC2318
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Garden / Patio - Rural Location - Woodburning Stove
    Blending contemporary comfort and awash with character, this former church makes a wonderful base for a holiday. Blending contemporary comfort and awash with character, this former church makes a wonderful base for a holiday.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    The Old Church is a stunning, unique property located in the delightful hamlet of Alton in rural Derbyshire. It has beautiful architectural features coupled with a spacious and classy interior, and the finish throughout is truly exceptional. The Old Church is situated in the heart of this pretty little hamlet on the outskirts of the village of Ashover, a previous winner of ‘Village of the Year’. It is just 6 miles from the very popular tourist town of Matlock and is...

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

    The Old Dairy

    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    Set on the owners’ farm with far-reaching countryside views, this detached barn conversion offers modern facilities along with original exposed stone and wood. This working farm with cattle, ducks, geese, chickens and horses is an ideal holiday location (stabling available). Walks from the doorstep and coarse fishing ½ mile away. Helicopter rides available locally (weather permitting). Close by are Chesterfield, Ashover, Matlock, Chatsworth House and Bakewell. Golf and...

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

    Runner Duck Cottage

    Cutthorpe, near Chesterfield, Derbyshire

    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
    Enjoy the peaceful countryside surrounding this cosy cottage, with miles of footpaths direct from your door.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    The fabulously named Runner Duck Cottage can be found surrounded by glorious Derbyshire countryside in a rural location offering simply stunning views. Set on the grounds of the owners’ home, which is also shared with horses and ducks, the detached cottage is stone built and perfectly placed for outdoor enthusiasts with access to miles of public footpaths direct from the door. Cutthorpe itself is a sleepy village on the edge of the Peak District National Park, with three local pubs...
  • Alton, near Matlock, Derbyshire
    Alton, near Matlock, Derbyshire×

    The Malt Shovel

    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    This attractive detached barn has been thoughtfully converted retaining many beams and is situated in the grounds of the owner’s home in the delightful rural hamlet of Alton, just 7 miles from Matlock. The original farmhouse is early 19th century and was historically both a working farm and a pub. Featured as one of the doctors’ houses in Peak Practice, this makes an excellent base for visiting all the Peak District has to offer, with Chatsworth House and Haddon Hall close...

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