Check-in

Add dates

Check-out

Add dates

Now driving your route . . .

Holiday Cottages in Chesterfield

Holiday Cottages in Chesterfield

Home to the biggest range at the lowest price

Check-in

Add dates

Check-out

Add dates

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

  • Last Minute Cottages - Smithy Cottage
  • 1

    Derbyshire

    Smithy Cottage

    Ref: S778604

    Reviews 18

    2
    4
    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

    £70

    per night
    View

  • Last Minute Cottages - 2 Bed Cottage in Barlow
  • Derbyshire

    2 Bed Cottage in Barlow

    Ref: S231781

    2
    4
    Additional information and rules No dogs allowed - Two bedrooms - king size bedroom and twin bedroom with zip and link that can be turned into a double at request. - Two Bathrooms (one on each bedroom floor) - Off road parking - Fridge w/...

    From

    £120

    per night
    View

  • Last Minute Cottages - The Lily Pad
  • Derbyshire

    The Lily Pad

    Ref: S1039765

    3
    6
    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

    £90

    per night
    View
    Partner deal

  • Last Minute Cottages - Mill Close Cottage
  • 3

    Derbyshire

    Mill Close Cottage

    Ref: S1042557

    2
    4

    From

    £96

    per night
    View
    Partner deal

  • Last Minute Cottages - Cottage Style 3 bedroom House - Close to City centre & The Peaks
  • Derbyshire

    Cottage Style 3 bedroom House - Close to City centre & The Peaks

    Ref: S919933

    3
    6

    From

    £128

    per night
    View
    Partner deal

  • Last Minute Cottages - Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & the Peak District
  • 3

    Derbyshire

    Tapton View - Modern Stay Near Chesterfield Town Center, Train Station & the Peak District

    Ref: S967352

    2
    6

    From

    £109

    per night
    View
    Partner deal

  • Last Minute Cottages - Byron House
  • Derbyshire

    Byron House

    Ref: S1037756

    5
    13

    From

    £399

    per night
    View
    Partner deal

  • Last Minute Cottages - Keswick House Chesterfield by Smart Corporate Stays
  • Derbyshire

    Keswick House Chesterfield by Smart Corporate Stays

    Ref: S1042185

    5
    16

    From

    £508

    per night
    View
    Partner deal

  • Last Minute Cottages - Holland House
  • Derbyshire

    Holland House

    Ref: S512842

    5
    18

    From

    £613

    per night
    View
    Partner deal

  • Last Minute Cottages - Cruck Barn Cottage
  • Derbyshire

    Cruck Barn Cottage

    Ref: S1232756

    1
    2

    From

    £120

    per night
    View

  • Last Minute Cottages - Cara
  • Derbyshire

    Cara

    Ref: S285599

    Reviews 76

    1
    2
    Located on a small farm in the attractive village of Holymoorside, Cara is a charming cottage with superb features. The spacious lounge and dining area boasts wonderful views of the garden and the surrounding countryside and is perfect for a...

    From

    £69

    per night
    View

  • Last Minute Cottages - Highview Stables
  • 1

    Derbyshire

    Highview Stables

    Ref: S1048522

    1
    4
    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

    £97

    per night
    View

  • Last Minute Cottages - Woodthorpe Cruck Cottage
  • Derbyshire

    Woodthorpe Cruck Cottage

    Ref: S162153

    Reviews 86

    3
    6
    Clay Cross is a small town resting close to the Peak District National Park and houses a selection of shops, pubs and restaurants. Within a few miles you will find the market town of Chesterfield which is known as the gateway to the Peak District....

    From

    £238

    per night
    View

  • Last Minute Cottages - Cherry Tree Cottage
  • 1

    Derbyshire

    Cherry Tree Cottage

    Ref: S880279

    Reviews 24

    1
    4
    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

    £130

    per night
    View

  • Last Minute Cottages - The Windmill Granary
  • 1

    Derbyshire

    The Windmill Granary

    Ref: S901407

    Reviews 11

    3
    4
    Experience countryside hikes, rewarding cycling trails and exciting local attractions from this comfortable, family-friendly holiday home. Right on the edge of the Peak District (5 miles), just 4.5 miles from Chesterfield, you’re well positioned...

    From

    £110

    per night
    View

  • Last Minute Cottages - Cedar Holme
  • 2

    Derbyshire

    Cedar Holme

    Ref: S372732

    Reviews 80

    2
    4
    Nestled on the edge of the Peak District National Park is the quaint village of Wingerworth. First recorded in the Domesday Book of 1086 aas a community of fourteen houses of freemen, Wingerworth is now a delightful settlement that boasts a...

    From

    £97

    per night
    View

  • Last Minute Cottages - Swallows Barn
  • Derbyshire

    Swallows Barn

    Ref: S425933

    Reviews 34

    2
    4
    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

    £94

    per night
    View

  • Last Minute Cottages - Elm Croft
  • 1

    Derbyshire

    Elm Croft

    Ref: S285580

    Reviews 40

    1
    2
    Produced to a top-notch standard, this stunning little cottage is the perfect place to relax in after a hard day exploring the local area. The underfloor heating and log burning stove makes this property super cosy for couples to enjoy, along with...

    From

    £60

    per night
    View

  • Last Minute Cottages - The Bungalow@Barlow
  • 2

    Derbyshire

    The Bungalow@Barlow

    Ref: S394847

    Reviews 45

    2
    4
    Often known as the 'Gateway to the Peak District', due to its ideal location providing easy access to the beautiful surrounding areas, is the historic town of Chesterfield. Boasting an impressive 1th-century church, local markets which offer...

    From

    £119

    per night
    View

  • Last Minute Cottages - Robin Glamping Retreat
  • Derbyshire

    Robin Glamping Retreat

    Ref: S854144

    Reviews 1

    1
    4
    Surrounded by an array of thrilling adventures, you'll be spoiled for choice. Immerse yourself in the grandeur of Chatsworth House (7.1m), where magnificent architecture, renowned art collections, and expansive gardens await exploration. Journey...

    From

    £150

    per night
    View

  • Last Minute Cottages - Park Corner
  • 1

    Derbyshire

    Park Corner

    Ref: S376244

    Reviews 13

    3
    6
    Park Corner is a very modest name for this stunning centuries-old house set in the rolling countryside south of the historic town of Chesterfield. Behind its handsome and stylish façade, you will find lots of superb accommodation. Just think...

    From

    £168

    per night
    View

  • Last Minute Cottages - 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

    £147

    per night
    View

  • Last Minute Cottages - 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

    £393

    per night
    View

  • Last Minute Cottages - Moor Farm Cottage
  • Derbyshire

    Moor Farm Cottage

    Ref: S778600

    Reviews 32

    2
    4
    The small, rural village of Ashover is peacefully situated in the Amber Valley, just five miles from Matlock. The village has several good pubs, including the Crispin Inn, renowned as one of the oldest pubs in the Peak District and The Old Poets’...

    From

    £194

    per night
    View
    Showing 1 - 24 of 82 properties

    Chesterfield Holiday Cottages

    Chesterfield presents a brilliant balance between the rugged beauty of the Peak District and the urban life of a bustling market town, with superb transport links and a packed calendar of events all year round. Chesterfield holiday cottages make for a great base from which to explore the surrounding areas.

    Famous for its 800-year-old open-air market, Chesterfield offers fantastic shopping opportunities from a variety of both chain and independent retailers, as well as seasonal local produce available. There’s plenty of entertainment, business and leisure activities available in the town. Just a short stroll out of the centre will take you to the ‘Palace of the Peak’ at Hardwick Hall, dating back to Elizabethan times, and Chatsworth, with guided and solo tours available of its stunning house and gardens. The town’s iconic crooked church spire dominates the skyline and is instantly recognisable from miles around.

    Snaptrip has thousands of holiday cottages across the UK, including in Chesterfield, listed on its system. What's more: every booking made through the site is covered by our unbeatable best price guarantee. Our friendly customer service team are available on the phone until 9:30pm daily to give you a helping hand.

    Locations to visit near Chesterfield

    Love the Peaks? Don't forget to check out these staycation destinations:

    Read more > less >

    Reviews

    What our customers say about their holidays

    • Lisa - Verified booking

      As previously described by another guest, we were fully aware that the pub opposite received early deliveries and we shouldn't expect to sleep in.

      .. Not really an issue for us, as we're early risers. This is outside of the operators control, but perhaps is worth noting for some. The property is lovely and comfortable, and it's great to have off road parking. The beds are firm, but we found them comfortable and we had a great nights sleep . Kitchen pretty much has everything you need, however I would recommend that more crockery is provided, i.e. dining plates and even tea plates, although I appreciate they're not standard these days, but a biscuit really does look lost on those big plates. It's clear from the feedback made already that they take the comments seriously and they are proactive to remedy issues raised, apologies, I didn't have time to fill in the visitors book! Literally pub on your door step and around the corner a lovely cafe with fresh made pies and cakes and a great breakfast too, wished we'd discovered it earlier in our stay. Good information pack available, however I would suggest a few tweaks and to the advertising descriptions, happy to expand on this if the owner/operator wants to get in touch direct.

      Read more less >

    • Mark - Verified booking

      Absolutely fantastic place to stay.

      Cottage had everything you could possibly need. The cottage was spotless with a fully equipped kitchen that had everything from a teaspoon to a first aid kit. The lounge had really good quality furniture that was very comfortable, really strong Wi-Fi (which you will need as internet service isn’t the best in the area ) and a smart tv on the wall. There is a separate room that houses the asking machine under the stairs. We only used the double bed as there was only 2 of us. OMG it was so comfortable. Good quality furniture and bedding makes all the difference. The bathroom had a walk in shower that had plenty of constant hot water. The heated towel rail warmed the room up lovely. The window blinds throughout the house were really thick so blocked out the light for a good nights sleep. The only thing I would maybe suggest would be a blind on the front door to block out the light from the pub across the road. This is only for spoilt dogs like ours that are used to sleeping in the dark

      Read more less >

    • Maura & Ray - Verified booking

      We hadn't visited the Peak District for many years and were very pleased we chose 'Cara' as the base for our holiday. We received a warm welcome from Suzanne. The cottage is in a perfect position with excellent views over the surrounding countryside. So peaceful - the perfect place for a relaxing holiday. The cottage is very comfortable and spacious with everything you need to self cater. We loved the personal touches of the framed needlework throughout the cottage and the old Singer sewing machine in the sitting room. Reminded me of my teenage years using the family treadle Singer machine!! 'Cara' is ideally situated for easy access to the main roads which will take you to the many popular haunts in the Peak District. Places we recommend to visit: The National Tramway Museum, Eyam Village Museum, Cascade Gardens at Clatterway, Bonsall, nr Cromford.

      Read more less >

    • Tom and Celia - Verified booking

      What a wonderful part of the world. The weather's been kind, the hills have been steep, the air has been fresh and we've had a delightful week's break from the traffic- filled lifestyle of Essex. We've cycled here, there and everywhere and really want to come back for more. The dedicated cycle tracks stretch far and wide and we've stopped to chat to so many people. We've photos and videos galore to remind us of our holiday. Cara cottage is perfect. Comfy bed, all mod cons, big TV for the evening and a safe place for the car. We've really enjoyed our time here and would recommend the cottage unreservedly. We swam in the open air Lido in Hathersage , looked at the Derwent reservoir, loved Bakewell and Matlock and Chesterfield. Went to Hardwick Hall and Ilam's Stepping Stones, and loved the Monsal and High Peak trails. Thank You

      Read more less >

    • Lynn - Verified booking

      The property is very well maintained and spotlessly clean.

      The beds are very comfortable and the shower is lovely and warm. Bedding and towels are high quality. The kitchen is very well equipped and there was a lovely welcome pack. The description is accurate and there were folders of helpful information on the surrounding area. The cottage was warm and cosy. It is directly opposite a beautiful pub with its own brewery. Just round the corner is a Hackney House cafe and bakery. It sells amazing croissant, pies, quiches and cakes to take away. We would not hesitate to return. The only slight issue would be if you were a party of four as there is only comfortable seating for three. We also would have appreciated a coffee table that we could have eaten our meals from as the dining table is really tiny. That won’t stop us coming back though. This is a lovely cottage.

      Read more less >

    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 >

    Things to do near Chesterfield

    • Landmark Landmark
    • Natural Landmark Natural Landmark
    • Activity Activity
    • Education Education
    Bolsover Castle
    A lavish castle with stunning views and extensive grounds complete with a picnic area. There is also a cafe to visit for a cuppa once you finish exploring. Free parking is available and dogs on leads are welcome in the grounds but not in the castle itself.

    Lumsdale Valley

    Just outside the Peak District town of Matlock, Lumsdale Valley was once a bustling hive of industrial activity. Now managed by Lumsdale residents and the Arkwright Society, the important woodland and wetland area is safeguarded for all to enjoy. Child and dog friendly, though it's recommended you keep your dog leashed.

    Kelham Island Museum

    Sheffield industrial history museum. Exhibitions, working machinery, activity areas and events all bring the past to life. Disabled access, parking and cafe.

    Sheffield Winter Garden

    Sheffield Winter Garden - one of the largest glasshouses built in the UK. Stroll through this green oasis that houses 2,500 plants from around the world.

    Crich Tramway Village

    Restored period village in Derbyshire, home to the National Tramway Museum and a selection of gift shops, cafes and pubs. Groups welcome. Disabled access.

    Gullivers Kingdom Matlock

    Gulliver's Kingdom is a theme park in Matlock Bath. Rides include a Log Flume, JCB zone and Gully's Magic Bikes. Attractions & experiences include the Lost World of the Living Dinosaurs, a Pirate Training Camp, and a Junior Cowboy Town. It hosts themed days such as a Dinosaur Sleepover. Cafes and food stalls.

    Weston Park Museum

    Free museum in Weston Park near Sheffield. A variety of historical exhibits such as Egyptian mummies & Snowy the polar bear & live ants & bees. Disabled access.

    National Emergency Services Museum

    Explore the history of Britain's emergency services at the National Emergency Services Museum. Discover the vehicles, equipment, and stories of firefighters, police officers, and ambulance crews from the 19th century to the present day. Try on uniforms, sit in a fire engine, and take part in interactive exhibits. Located at West Bar, Sheffield S3 8PT

    Abbeydale Industrial Hamlet

    Abbeydale Industrial Hamlet in Sheffield is a unique experience that takes visitors on a journey through the region's industrial heritage. The hamlet is a preserved 18th-century steelworks site with fully-functioning water-powered machinery, workshops and cottages. Visitors can witness the fascinating steel-making process, explore the interactive exhibitions, and enjoy the beautiful surrounding woodland. Address: Abbeydale Rd S, Sheffield S7 2QW

    Sheffield Hallam University

    Sheffield Hallam University is a public research university located in the city of Sheffield, England. The university has a strong focus on professional and vocational programs, with a particular emphasis on fields such as business, engineering, and healthcare. Sheffield Hallam is also known for its commitment to sustainability and social responsibility, with a range of initiatives in place to promote environmental awareness and community engagement. Main campus: City Campus, Howard Street, Sheffield, S1 1WB

    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

    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.

    Your browser is out of date and we can't guarantee a consistent experience when using our site. Please consider updating or switching. More info on browser support