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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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  • 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, 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...

  • 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
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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 has gas fire and electric heaters and comprises:...

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • 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
    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 is all at ground floor level, has gas central...

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

    Ashmore Cottage

    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.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    This attractive 18th century stone cottage is situated between Clay Cross and Ashover. It has a garage and an enclosed garden. It is within easy reach of the ’crooked spire’ town of Chesterfield, also Bakewell and Matlock. An ideal base for a holiday exploring the Peak District, Nottinghamshire (Robin Hood country) and South Yorkshire. Several stately homes and NT properties are less than 30 minutes’ drive away. Horse riding, golf and choice of fishing venues are...

  • Tibshelf, near Alfreton, Derbyshire
    Tibshelf, near Alfreton, Derbyshire×

    Hunters Cottage

    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.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    This wonderful terraced cottage offers delightful open-plan living with a light and airy feel, with French doors opening onto a pretty garden and patio where you can enjoy your very own private hot tub. Thoughtfully renovated to offer guests quality accommodation with a personal touch, Hunters Cottage will definitely not disappoint. Sitting directly on the famous Five Pits Trail which follows the route of the Great Central Railway, which was used to serve the five deep collieries in the...
  • Barlow, near Chesterfield, Derbyshire
    Barlow, near Chesterfield, Derbyshire×

    The Barn at Woodland View

    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.
    Prices from
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    Pets included
    Pets go free

    Accommodation at


    This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living and kitchen area with its stunning beamed vaulted ceiling creates a warm and cosy social environment. Located on the owners grounds, thoughtful additional extras can be provided at the owners discretion where possible making the full stay an extra special experience....

  • 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
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    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...

  • Barlow, Derbyshire
    Barlow, Derbyshire×

    The Cottage

    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.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    This beamed, single-storey, semi-detached cottage is set within 17 acres of open rolling countryside near the Peak District National Park. Buxton, Bakewell, Matlock and Castleton are only a short drive away offering a wealth of activities including caves and attractions such as the Heights of Abraham, providing breathtaking cable car rides across the Derwent Valley. The start of the Pennine Way with excellent walks and Chesterfield with its famous crooked spired church are only a short...
  • 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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