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

    Or search by driving time
    From my postcode
    Locate me
    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 - 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

    £131

    per night
    View

  • Last Minute Cottages - The Cottage

    • Derbyshire

    The Cottage

    Ref: S801932

    Reviews 11

    2
    4
    Located on the edge of the Peak District National Park in Derbyshire, between Matlock and Chesterfield, is the tiny village of Stone Edge. Despite being well-known for its industrial past, the hamlet now draws a wide variety of tourists,...

    From

    £112

    per night
    View

  • Last Minute Cottages - The Tack Room Cottage
    • 1

    Derbyshire

    The Tack Room Cottage

    Ref: S39652

    Reviews 47

    3
    6
    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

    £117

    per night
    View

  • Last Minute Cottages - Cedar Cottage
    • 2

    Derbyshire

    Cedar Cottage

    Ref: S521502

    Reviews 15

    3
    6
    Hollingwood is a quaint historic village in Derbyshire, situated between Barrow Hill and Chesterfield. The community is well-known for its proximity to the Chesterfield Canal, which includes a helpful visitor centre that draws a large number of...

    From

    £60

    per night
    View

  • Last Minute Cottages - The Old Stables

    • Derbyshire

    The Old Stables

    Ref: S39657

    Reviews 86

    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

    £145

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Chatsworth stables

    • Derbyshire

    Chatsworth stables

    Ref: S940791

    1
    4

    From

    £82

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Number 26 Van Dyk Village
    • 3

    Derbyshire

    Number 26 Van Dyk Village

    Ref: S1034047

    3
    5

    From

    £162

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Cedar Cottage

    • Derbyshire

    Cedar Cottage

    Ref: S524823

    3
    6

    From

    £69

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Blissful Barrys
    • 3

    Derbyshire

    Blissful Barrys

    Ref: S990766

    3
    5

    From

    £135

    per night
    View
    LateRooms.com

  • 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

    £132

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Middlecroft House Staveley by Smart Corporate Stays

    • Derbyshire

    Middlecroft House Staveley by Smart Corporate Stays

    Ref: S944759

    4
    10

    From

    £346

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Hady House

    • Derbyshire

    Hady House

    Ref: S1037868

    5
    11

    From

    £395

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Dryden House

    • Derbyshire

    Dryden House

    Ref: S510288

    5
    16

    From

    £587

    per night
    View
    LateRooms.com

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

    • Derbyshire

    Keswick House Chesterfield by Smart Corporate Stays

    Ref: S1042185

    5
    16

    From

    £540

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Little Hillside
    • 3

    Derbyshire

    Little Hillside

    Ref: S938376

    1
    2

    From

    £78

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Walton Cottage - 2 Beds - Sleeps 4 - Pet Friendly
    • 3

    Derbyshire

    Walton Cottage - 2 Beds - Sleeps 4 - Pet Friendly

    Ref: S1046917

    2
    4

    From

    £119

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Park Corner
    • 3

    Derbyshire

    Park Corner

    Ref: S938359

    6

    From

    £191

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Little Manor
    • 3

    Derbyshire

    Little Manor

    Ref: S958261

    2
    6

    From

    £94

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Stonelow Cottage
    • 3

    Derbyshire

    Stonelow Cottage

    Ref: S987485

    3
    6

    From

    £379

    per night
    View

  • Last Minute Cottages - Riber View Barn
    • 2

    Derbyshire

    Riber View Barn

    Ref: S123614

    Reviews 83

    2
    4
    The rural village of Ashover is situated in the Amber Valley, just five miles from Matlock, with several good pubs. The county town of Matlock offers a host of eating places, shops and a museum, whilst at the heart of the town, Leys Hall Park...

    From

    £75

    per night
    View

  • Last Minute Cottages - The Tower

    • Derbyshire

    The Tower

    Ref: S801731

    1
    2
    The town of Bolsover in Derbyshire has been around since before the time of the Domesday Book. The region features a variety of retail establishments, dining options, and drinking establishments, in addition to green spaces and recreational...

    From

    £153

    per night
    View

  • Last Minute Cottages - Tuliptree

    • Derbyshire

    Tuliptree

    Ref: S375576

    Reviews 22

    2
    4
    Resting in the picturesque Amber Valley and only five miles away from the thriving town of Matlock, is the quaint village of Ashover. You will find everything you need right on your doorstep in Ashover, from a selection of welcoming pubs,...

    From

    £69

    per night
    View

  • Last Minute Cottages - Overton
    • 1

    Derbyshire

    Overton

    Ref: S853948

    Reviews 2

    4
    8
    Chesterfield, a historic market town that serves as a gateway to the Peak District, is a popular tourist destination. The town's 14th-century church, known for its "Crooked Spire," which diverges curiously from the building's true centre, has...

    From

    £125

    per night
    View
    LateRooms.com

  • Last Minute Cottages - Mill Close Cottage
    • 3

    Derbyshire

    Mill Close Cottage

    Ref: S1042557

    2
    4

    From

    £95

    per night
    View
    Showing 1 - 24 of 26 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

    • Tim - Verified booking

      The Tack Room Cottage is a beautifully re-furbished out-building in an idyllic farmstead setting, in a small complex of stone buildings, courtyards and gardens, with an elegant small 'manor farmhouse' at its heart.

      The whole is surrounded by pastures and woodland belonging to the property, allowing a fair bit of walking whilst hardly leaving the grounds. This includes seven minutes to your very own 'Farm Shop and Cafe', extremely friendly and well-stocked with self-catering treats, liquid and otherwise, and a perfect place for 'brunch' made largely of home grown or very local fresh food. The local area, just outside the Peak District National Park, is classic, English countryside: deep valleys with woods and running streams, high moorland, unspoilt villages clustered round their churches and traditional pubs. If you want peace and quiet, you've got it! If you like a heritage site to visit, Chatsworth is unmissable: both the house and the gardens are worth every penny and every minute of a few hours at a time. We went twice, once for the gardens (with grandchildren) and once for the house (by ourselves). Coming back to the cottage itself, it can cope well enough with two couples and two children, accommodation-wise, though the kitchen - and especially the fridge - did struggle for space a bit (we arrived in a heatwave!) The only other thing we would have different (in an ideal world) is more daylight in the main living room - just one window to see out of would be nice. On the odd rainy day, being cooped up in the house felt a little claustrophobic. This was apparent from an earlier review, so we were happy to accept it as it was and not let it spoil the holiday. When the sun was shining, we used the small, pretty back lawn for meals and drinks. The outside table and chairs there were fine but there was nothing to lounge on, so bring your own loungers or a rug, if that's what you like! The owner, Lesley, was fantastic. Nothing was too much trouble. We were left to our own devices unless we asked for something - such as re-booting the wi-fi router, which there was quite a need of for a day or two. There were plans to address that, so it may no longer be an issue; and it worked well anyway, with good bandwidth, most of the time. We went away with a couple of bags of lovely fresh vegetables from the next door garden, too - very generous and very tasty! To cap all that, we left something quite precious behind (it had slipped under a wardrobe) and Lesley followed up on it assiduously. The cleaners found it, on looking again, and it was posted back to us without charge. You could not wish for warmer or better organised hospitality!

      Read more less >

    • Shelagh - Verified booking

      The location was good, the cottage was cosy and bedrooms comfortable.

      Setting was beautiful and it was a good base to explore the area. However there were a few things which we feel need addressing. Directions were inaccurate and all of us struggled to find the entrance to the Tack Room. We selected the property as it was stated that it was a ten minute walk to the local pubs. This walk along the roads would have taken a lot longer and in places on the country lane there was no pavement or lighting. Maybe it takes that time a walk across the fields but this isn’t an option at night. A sensory light would be useful on the steps to the property as it was dark and slippery in the rain. The living room has no windows and was disappointingly dark. The small step to the kitchen is a hazard and one of our group had a nasty fall. We expect to find kitchen basics such as salt and pepper, oil, tea, coffee, foil, cling film- none of these were provided 9.30am check out we thought was a little early especially when we were expected to strip beds, empty bins and dishwasher. The guests in the other cottage were also unhappy about the check out time

      Read more less >

    • Lisa - Verified booking

      We had a great week at the Tack Room.

      The place was spotless and had every home comfort we needed. A lovely welcome pack on arrival made settling in easy. The beds were very comfy, rooms felt spacious and furnishings were modern and well looked after. The village had a lovely pub and was quiet and quaint, lovely for an evening stroll. The cottage is in a great location for lots of the main tourist attractions. The owners very friendly, on hand but didn’t interfere just as we like it. The garden was nice and secluded. Although there is another cottage on site we hardly saw the other tenants and were not disturbed by their being around. My one criticism would be the amount of natural light in the downstairs. Had the weather been more sunny I would have felt we had missed out as there is very little natural light in the lounge area. This was mentioned in other reviews. Whilst it didn’t ruin the holiday it did make being indoors a slightly less enjoyable experience. However, other aspects of the cottage and location made up for it.

      Read more less >

    • Michelle - Verified booking

      The Cottage is everything you could ask for from a first class holiday rental.

      It has everything you could need for your stay. It was spotless, beautifully decorated and very well appointed to allow you to enjoy your break. Being open planned and all on one level meant I was able to get around very easily even with limited mobility. We were welcomed by Liz, who is genuinely the loveliest host and greeted by a delicious welcome basket of goodies. Our neighbours, the farm’s herd of cows, were delightful and kept us entertained. The fabulous farm shop and tea room next door provided us with the most delicious local produce for breakfast and tea. The Cottage looks out over the beautiful hillsides of the Peak District and was a great base from which to visit Bakewell, Buxton, Matlock and all the other local attractions. We really couldn’t have chosen a better place to stay for our first (but not last) holiday in the Peak District. A big, BIG, thank you to Liz and the team for making our stay AMAZING.

      Read more less >

    • Helen - Verified booking

      The pre arrival brochure, I got was very detailed, and the preference sheet, on how I would like the cottage set up showed attention to detail and the intention to go above and beyond for guests.

      I was greeted at the gate, and given a very detailed show round the pictures online do not do the cottage justice, it is beautiful. What is most amazing is that Lesley and Andrew have put so many amazing treats and extras on for guests. The main bathroom has a basket of toiletries, scrunchies for washing yourself, huge towels on huge radiators, and it has under floor heating. In the lounge the most incredible welcome basket, with coffee, Tea, chocolates, biscuits, sweets, local honey brilliant. Also Fresh flowers on the table. In the kitchen washing up, scrubbers etc they have thought of everything. It's stunning courtyard with big modern hot tub, and views over the fields. Lesley and Andrew are superb hosts, and I wish them luck on this new venture, genuine hardworking people it was a pleasure to meet them.

      Read more less >

    Trustpilot

    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