21,000+ quality-checked cottages 30+ years of cottage holidays 98% would book again No credit card fees New home of cottages4you 21,000+ quality-checked cottages 98% would book again 30+ years of cottage holidays No credit card fees New home of cottages4you
Shortlist
You can view or make payments on your booking by clicking here x.

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.
26 
Add a date to get better results
default
Give your search a reference name and save it for later.
Save your search
  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

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

    Mill Farm Cottage - Kingfisher Cottage

    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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

    Mill Farm Cottages - Cherry Tree Cottage
    5
    2
    2
  • 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

    2
    1
    1
    1
    Ref: UKC2608
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Garden / Patio - Rural Location
    This is an ideal choice for couples looking for a romantic break, close to the picturesque Peak District National Park.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

    Green Farm Holiday Cottages - The Pig Sty
    4
    2
    2
  • 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!
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

    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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • Dore, near Sheffield, Derbyshire
    Dore, near Sheffield, Derbyshire×

    Pat’s Cottage

    Dore, near Sheffield, Derbyshire

    4
    2
    1
    1
    Ref: 30733
    Key Features:
    - Swimming pool - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    This 18th-century cottage is on the edge of the Peak District and has use of a heated swimming pool. This 18th-century cottage is on the edge of the Peak District and has use of a heated swimming pool.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

  • 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 - 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.
    0
    Pets included
    Pets go free
    Prices from

    Accommodation at

    Green Farm Cottages - The Old Cow Shed
    2
    1
    1

Subscribe to our latest deals & offers

×