Holiday Cottages in Chesterfield

Holiday Cottages in Chesterfield

Home to the biggest range at the lowest price

Check-in

{{checkInFormatted}}

Add dates

± {{flex}}
Check-out

{{checkOutFormatted}}

Add dates

± {{flex}}

Live availability

Live prices

Book instantly

Did you know? We have a dedicated site just for pet friendly holidays, take me to Dog Friendly Cottages >

Chesterfield Cottages

  • Snaptrip - Yew Tree Cottage
  • 3

    Derbyshire

    Yew Tree Cottage

    Ref: S1312026

    Reviews 30

    3
    6
    Tucked away in the countryside of Holymoorside, this quiet, a perfect base for walking, cycling and exploring the Peak District.. 2 steps to entrance. Ground Floor: Living room: Smart TV, Sky, Woodburner Kitchen/dining room: Breakfast Bar,...

    From

    £88

    per night
    View

  • Snaptrip - The Old Stables
  • Derbyshire

    The Old Stables

    Ref: S39657

    Reviews 97

    4
    8
    The small, rural village of Ashover is peacefully situated in the Amber Valley, just five miles from Matlock. The village affords a 9-hole golf course and several good pubs, including the Crispin Inn, renowned as one of the oldest pubs in the Peak...

    From

    £119

    per night
    View

  • Snaptrip - Swallows Barn
  • Derbyshire

    Swallows Barn

    Ref: S425933

    Reviews 34

    3
    6
    Chesterfield is a historic market town that serves as the entrance to the Peak District and has a great deal to offer visitors. The town's regular bustling market days are an excellent opportunity to explore the many diverse specialty shops and...

    From

    £104

    per night
    View

  • Snaptrip - Cherry Tree Farm
  • Derbyshire

    Cherry Tree Farm

    Ref: S1073179

    5
    10
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £262

    per night
    View

  • Snaptrip - Alton Hall Cottage
  • Derbyshire

    Alton Hall Cottage

    Ref: S1330161

    Reviews 27

    4
    8
    Comprising an 18th-century cottage and its neighbouring barn, this lovely property makes an ideal retreat for larger families or groups of friends.. Ground Floor: Living room: Freeview TV, Bluetooth Speaker, Playstation 4, Woodburner, Bi-Fold...

    From

    £200

    per night
    View

  • Snaptrip - Manor House
  • Derbyshire

    Manor House

    Ref: S4525

    Reviews 95

    5
    10
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £264

    per night
    View

  • Snaptrip - Greenwell Cottage
  • Derbyshire

    Greenwell Cottage

    Ref: S1317487

    Reviews 30

    4
    8
    A stunning high end cottage located within the popular town of Bolsover, with modern finishes and its own hot tub in a private yard.. Ground Floor: Dining room. Kitchen: Electric Oven, Electric Hob, Microwave, Fridge, Dishwasher, Washing...

    From

    £136

    per night
    View

  • Snaptrip - Spire Haven
  • Derbyshire

    Spire Haven

    Ref: S525509

    Reviews 25

    4
    8
    Chesterfield, the historic market town that serves as the Peak District's gateway, has a lot to offer visitors. The town's 14th-century church is known for its "Crooked Spire," which twists strangely from its actual centre, and the town's regular...

    From

    £91

    per night
    View

  • Snaptrip - The Loft at The George
  • 2

    Derbyshire

    The Loft at The George

    Ref: S517500

    Reviews 29

    4
    8
    Clay Cross is a small village near the Peak District National Park's boundary. There are numerous shops, taverns, and superb restaurants in the town. The old market town of Chesterfield, which serves as the gateway to the Peak District and has...

    From

    £83

    per night
    View

  • Snaptrip - The Mill Cottage
  • 2

    Derbyshire

    The Mill Cottage

    Ref: S1328725

    Reviews 33

    3
    8
    Ideally located on the Hardwick Estate, take the opportunity to explore the National Trust’s Hardwick Hall and Stainsby Mill, located just next door!. Ground Floor: Living room: Smart TV, Netflix, DVD Player, Bluetooth Speaker, Open...

    From

    £81

    per night
    View

  • Snaptrip - West Barn
  • Derbyshire

    West Barn

    Ref: S1325708

    Reviews 19

    4
    8
    Set in undisturbed surroundings and right by a stream, this quaint barn conversion oozes character and charm. Great location with many attractions close by.. Ground Floor: Living room: Freeview TV, DVD Player, CD Player, Ipod Dock,...

    From

    £156

    per night
    View

  • Snaptrip - The Pantiles
  • 2

    Derbyshire

    The Pantiles

    Ref: S1317498

    Reviews 2

    5
    9
    A fantastic house for all the family to gather, located in a great location central to the town amenities and restaurants.. 5 steps to entrance. Ground Floor: Living room: Smart TV, Netflix, Apple TV, Open Fire Dining room: Rayburn, Patio Doors...

    From

    £197

    per night
    View

  • Snaptrip - Hillcrest
  • Derbyshire

    Hillcrest

    Ref: S1311776

    Reviews 14

    5
    10
    This fabulous property is the ideal place to stay and relax before enjoying a fun night of singing and dancing.. Ground Floor: Living/dining room: 75" Freeview Smart TV, Netflix Kitchen: Electric Oven, Electric Hob, Microwave, American Fridge...

    From

    £165

    per night
    View

  • Snaptrip - 4 Bed Cottage in Chesterfield
  • Derbyshire

    4 Bed Cottage in Chesterfield

    Ref: S229999

    4
    10
    Additional information and rules No dogs allowed - 4 bedrooms: 1 king, 2 doubles, 1 bedroom with 4 single beds - 2 upstairs bathrooms, 2 downstairs bathrooms, additional toilet accessed from outside - 2 Woodburners - Ample off road parking ...

    From

    £398

    per night
    View

  • Snaptrip - Rent My Spa Home with Pool table, Hottub and Sauna
  • 2

    Derbyshire

    Rent My Spa Home with Pool table, Hottub and Sauna

    Ref: S2141003

    7
    20
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    From

    £878

    per night
    View

  • Snaptrip - The Old Cow Shed
  • 2

    Derbyshire

    The Old Cow Shed

    Ref: S1327605

    Reviews 58

    1
    2
    The Old Cow Shed is the perfect setting for relaxing in beautiful surroundings, exploring the Peak District or visiting the tourist attractions in the area.. All on the Ground Floor: Living/dining room: 50" Freeview TV, DVD Player, Bluetooth...

    Check for price

    View

  • Snaptrip - Willow Cottage
  • 1

    Derbyshire

    Willow Cottage

    Ref: S1323428

    Reviews 11

    1
    2
    Within a small countryside estate with great access to many walks and attractions. Ideal base for a couples walking holiday.. All on the Ground Floor: Living/dining room: TV, DVD Player, French Doors Leading To Patio Kitchen: Electric Oven,...

    Check for price

    View

  • Snaptrip - The Pig Sty
  • 2

    Derbyshire

    The Pig Sty

    Ref: S1327127

    Reviews 47

    2
    4
    The Pig Sty is perfect for relaxing in beautiful surroundings, actively exploring the Peak District or visiting many of the tourist attractions in the area.. Ground Floor: Living room: Freeview TV, DVD Player, Soundbar, Bluetooth Speaker,...

    Check for price

    View

  • Snaptrip - Chestnut Cottage
  • 2

    Derbyshire

    Chestnut Cottage

    Ref: S2021430

    Reviews 14

    2
    4
    A traditionally furnished barn conversion based on a small countryside estate between Chatsworth and Chesterfield. Great walks and nature trails from the door.. All on the Ground Floor: Living room: TV, DVD Player, French Doors Leading To...

    Check for price

    View

  • Snaptrip - The Bobbin
  • 2

    Derbyshire

    The Bobbin

    Ref: S1326616

    Reviews 44

    2
    4
    This cottage is perfect for outdoor enthusiasts with walking and cycle trails from the doorstep, or perhaps enjoy a get together with family or friends or romantic break away in beautiful surroundings.. Ground Floor: Open plan living...

    Check for price

    View

  • Snaptrip - Freebirch Barn
  • Derbyshire

    Freebirch Barn

    Ref: S1330448

    Reviews 7

    2
    4
    This light and airy converted barn is conveniently placed for Chatsworth House and the numerous attractions the Peak District has to offer.. Ground Floor: Living room/kitchen: Freeview TV, DVD Player, CD Player, Electric Fire, Electric Oven, Gas...

    Check for price

    View

  • Snaptrip - Acorn Cottage
  • 2

    Derbyshire

    Acorn Cottage

    Ref: S1310378

    Reviews 4

    2
    4
    A fantastic dog and family friendly cottage on a small working farm, in a peaceful rural location close to Peak District attractions, including Chatsworth.. Ground Floor: Living room: Smart TV, DVD Player, Woodburner Dining room. Kitchen:...

    Check for price

    View

  • Snaptrip - Tawny Owl Barn
  • 2

    Derbyshire

    Tawny Owl Barn

    Ref: S1323552

    Reviews 70

    3
    5
    Tawny Owl Barn is perfect for relaxing in beautiful surroundings, actively exploring the Peak District or visiting many of the tourist attractions in the area.. Ground Floor: Living room: Freeview TV, DVD Player, Bluetooth Speaker,...

    Check for price

    View

  • Snaptrip - Peak Avenue Retreat
  • 1

    Derbyshire

    Peak Avenue Retreat

    Ref: S1250633

    3
    5
    The historic market town of Chesterfield acts as the gateway to the Peak District, and has much to offer visitors. The town is famous for its 14th Century church with "Crooked Spire", twisting curiously from its true centre, while the frequent...

    Check for price

    View
    Showing 49 - 72 of 109 properties

    Best price guarantee

    No one can beat our prices

    ✕
    Best price guarantee

    Our cottages are professionally managed by our partners and payments are taken by them, but rest assured, by booking via Snaptrip you'll pay the lowest possible price for your trip.

    We never charge you more than you would pay booking directly on the partner's site and if you become a member you can save even more. If you find a property priced lower anywhere else on the internet (we’d be amazed if you do), simply email us at marketing@snaptrip.com and we'll refund you the difference.

    We bring it all together

    Biggest range of self-catering holiday properties

    We connect you to a range of great suppliers with a huge selection of properties. We've done the research, so that you don't have to.

    View properties >

    We get you
    the lowest price

    We help you to complete your booking whilst giving you discounts, member only prices and our best price guarantee.

    A marketplace
    you can trust

    We connect you with the best professionally managed properties and our marketing leading customer services can help you every step of the way.

    Start your journey >
    ✕

    Join for free to get access to exclusive prices on thousands of properties.

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    Sign up to see

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    Did you mean {{ suggestedEmail }}?

    or

    Already a member login here

    Not a member?

    By entering my email address, I agree to Snaptrip's Terms of service, Privacy policy and to receive email updates, news, & offers from Snaptrip.

    Welcome, member discounts are now available.