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Holiday Cottages in Chesterfield

Holiday Cottages in Chesterfield

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Chesterfield Cottages

  • 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

    £100

    per night
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  • Last Minute Cottages - Park Corner
  • 1

    Derbyshire

    Park Corner

    Ref: S376244

    Reviews 14

    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

    £155

    per night
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  • 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

    £67

    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 king size at request. - Two Bathrooms (one on each bedroom floor) - Off road parking for 2 cars ...

    From

    £96

    per night
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  • Last Minute Cottages - Five Acres
  • 3

    Derbyshire

    Five Acres

    Ref: S1028772

    7
    10
    This charming village is less than four miles from Newmarket and is a fantastic base with a local shop and pub which serves delicious meals from a seasonal menu. Set within easy travelling distance of some popular towns and villages including...

    From

    £994

    per night
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    Partner deal

  • Last Minute Cottages - The Olde Coach House
  • Derbyshire

    The Olde Coach House

    Ref: S922443

    3
    6
    Set in Chesterfield, 23 km from Utilita Arena Sheffield, The Olde Coach House provides accommodation with a hot tub and a fitness room. This property offers access to a patio, free private parking and free WiFi. The property is non-smoking and is...

    From

    £235

    per night
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    Partner deal

  • Last Minute Cottages - Morden house close to City centre & The Peaks
  • Derbyshire

    Morden house close to City centre & The Peaks

    Ref: S915261

    3
    6
    Offering a garden and garden view, Morden house close to City centre & The Peaks is located in Chesterfield, 20 km from Chatsworth House and 22 km from Utilita Arena Sheffield. Both free WiFi and parking on-site are available at the holiday home...

    From

    £146

    per night
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    Partner deal

  • Last Minute Cottages - Hady House
  • Derbyshire

    Hady House

    Ref: S1037868

    5
    11
    Offering a garden and inner courtyard view, Hady House is situated in Chesterfield, 25 km from Utilita Arena Sheffield and 28 km from Clumber Park. Both free WiFi and parking on-site are available at the holiday home free of charge. The property...

    From

    £323

    per night
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    Partner deal

  • Last Minute Cottages - Byron House
  • Derbyshire

    Byron House

    Ref: S1037756

    5
    13
    Byron House, a property with a garden and a shared lounge, is located in Chesterfield, 32 km from Clumber Park, 41 km from Sherwood Forest, as well as 41 km from Buxton Opera House. The property has garden and quiet street views, and is 25 km from...

    From

    £383

    per night
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    Partner deal

  • Last Minute Cottages - SpaHomeDotCom
  • Derbyshire

    SpaHomeDotCom

    Ref: S954768

    7
    20
    Situated in Chesterfield in the Derbyshire region, SpaHomeDotCom features accommodation with free WiFi and free private parking, as well as access to a sauna. A hot tub is available for guests, along with a fitness room. Clumber Park is 32 km from...

    From

    £941

    per night
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    Partner deal

  • Last Minute Cottages - SpaHome with Hottub Sauna bbq & Pool Table
  • 3

    Derbyshire

    SpaHome with Hottub Sauna bbq & Pool Table

    Ref: S529566

    7
    20
    Set in Chesterfield, 25 km from Utilita Arena Sheffield, SpaHome with Hottub Sauna bbq & Pool Table provides accommodation with a hot tub. This property offers access to a patio, free private parking and free WiFi. The property is non-smoking and...

    From

    £852

    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

    £100

    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

    £82

    per night
    View

  • Last Minute Cottages - The Windmill Granary
  • 1

    Derbyshire

    The Windmill Granary

    Ref: S901407

    Reviews 13

    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 - 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

    £149

    per night
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  • 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

    £65

    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

    £134

    per night
    View

  • 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

    £62

    per night
    View

  • Last Minute Cottages - 1 Bed Cottage in Barlow
  • Derbyshire

    1 Bed Cottage in Barlow

    Ref: S284190

    1
    2
    Additional information and rules No dogs allowed - 1 double bedroom - 1 en-suite shower room with shower and WC - Electric oven and hob, fridge, freezer, dishwasher, washing machine and microwave - Smart TV in the lounge and bedroom -...

    From

    £122

    per night
    View

  • Last Minute Cottages - Squirrel Glamping Retreat
  • Derbyshire

    Squirrel Glamping Retreat

    Ref: S854084

    1
    4
    With lots of wonderful adventures on your doorstep, you will be spoilt for choice. Immerse yourself in the grandeur of Chatsworth House (7 miles), where beautiful architecture, renowned art collections, and sprawling gardens await. There is the...

    From

    £134

    per night
    View

  • Last Minute Cottages - 1 Bed Cottage in Barlow
  • Derbyshire

    1 Bed Cottage in Barlow

    Ref: S231036

    1
    2
    Additional information and rules No dogs allowed - 1 Bedroom - King size - 1 Bathroom - Electric oven and induction hob, fridge/freezer, dishwasher and washer/dryer - Nespresso machine - Wood burner - logs included - Off-road parking for...

    From

    £93

    per night
    View

  • Last Minute Cottages - Temperance Croft
  • Derbyshire

    Temperance Croft

    Ref: S899979

    Reviews 6

    1
    2
    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

    £59

    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 - The Old Grocery
  • 2

    Derbyshire

    The Old Grocery

    Ref: S50128

    Reviews 49

    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

    £58

    per night
    View
    Showing 1 - 24 of 73 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

    • Dawn - Verified booking

      Just got back from a week stay at Woodthorpe Cruck cottage.

      Upon arrival the cottage was clean and there was a lovely welcome basket which was really appreciated. There was lots of information in the cottage for things to do in the area and guidance for the cottage. The surroundings were stunning and the cows were a lovely sight, the kids loved them. Some points or suggestions would be: 1) There is a drain smell coming from the downstairs wet room. Was particularly bad in the living room. We had to buy air freshener to help. 2) Some stepping stones would be beneficial from the cottage to the hot tub and robes provided considering farm workers can be on the property at anytime of the day (as we established during our stay) 3) Give guests the option to adjust the temperature of heating as they feel comfortable. Most days the cottage was really warm, too warm, and we had to leave all windows open, which meant lots of fly's in the property. 4) A sign at the end of the drive would be beneficial as the entrance kind of jumps on you. The vending machines at the end of the drive are a great idea, but could do with a spruce up. And the pictures updated on Sykes website would be beneficial also. 5) The kids games and books were old and tired and of no real interest to our children (5 and 11). Maybe these could be updated and maybe a DVD player and a small selection of DVDs would be a great addition. We would also like to leave a comment here for other guests, (mainly for reassurance reasons) about an incident that took place while we were there. One evening at around 7.30pm, we were surprised to see a man standing at the wall of the cottage staring into the kitchen windows. He then moved to near the gate, staring into the dining room windows. He was there around 2 minutes in total. He really caused concern to our children so we contacted the owner to see if this person was known to them. We was reassured that he was and they also suggested that this was to be expected as the cottage is on a working farm (which we knew about when booking) Initially I said this was fine, as I was relieved that the man wasn't a stranger to the owners. However, afterwards i have felt that his behaviour was in appropriate. I respect and understand the cottage is on a working farm and the farmer workers should attend to farming duties when needed. However, looking into the property where guests are staying for as long as he did, we feel wasn't usual farming duties or behaviour and did make us feel uncomfortable at the time. I felt it was important to add this to my review for future guests reassurance incase it happens again. Especially those with children. I would suggest maybe a note somewhere telling future guests that they may see farm workers actually on the cottage property in the evening and not just working there in the day. I also think the owner and farm workers need to be aware of how this made us feel and maybe some tighter boundaries around respecting guests privacy too. Other than the above incident, we enjoyed our stay at Woodthorpe, nice cottage, beautiful surroundings.

      Read more less >

    • Matthew - Verified booking

      We recently had the pleasure of staying at a charming cottage that truly exceeded my expectations.

      From the moment we arrived, the picturesque surroundings approaching the cottage and the warm, inviting atmosphere of the cottage made it feel like a home away from home. The cottage itself is beautifully appointed, seamlessly blending traditional charm with modern comforts. The decor strikes a perfect balance between rustic elegance and practicality. The living room, with its cozy fireplace, invites you to curl up with a good book or enjoy a movie night after a day of hiking. The kitchen is well-equipped, making it easy to prepare meals with fresh, local ingredients from nearby markets. The bedroom was spacious and comfortable, adorned with soft linens and cozy throws. Waking up in such a serene environment was a luxury, and each morning felt like a refreshing retreat. The host was exceptionally friendly and accommodating. They had thoughtfully prepared a welcome basket filled with slippers for the hot tub and robes to wear, they also had treats for the dog in a jar with his name on it which was a delightful touch. The level of detail and care put into the stay truly made a difference. Overall, our experience at this beautiful cottage near the Peak District was nothing short of magical. Whether you’re looking to escape for a romantic getaway, or a solo retreat, this cottage has it all. I cannot recommend it highly enough – it’s a perfect blend of comfort, beauty, and adventure. We left feeling recharged and inspired, already planning our next visit!

      Read more less >

    • Tina - Verified booking

      What a beautiful place!

      We had an amazing time at Cherry Tree, the cottage itself is stunning, very spacious with a real homey feel. The hot tub is one of the best we’ve seen, private due to being partly-enclosed and waking up to the views started the day off perfectly. We visited the red lion pub, a stone’s throw away and that too was decorated to a very high standard, so cosy and welcoming. Hardwick Hall National Trust was really interesting, the stories from the volunteers were fascinating. Chatsworth Estate is well worth a visit too, even in the winter. And lastly Bakewell town centre, so quaint and lovely for a little stroll and some lunch. So many places to see, and we didn’t get to see half of them. I would definitely recommend Cherry Tree, it has everything you would want for a luxury stay as well as a great location. Thanks Andy and Clare for your hospitality x

      Read more less >

    • Amy - Verified booking

      We had such a wonderful stay at Woodthorpe Cruck Cottage, it's super cosy with tons of home comforts included - we definitely overpacked!

      The welcome package was a fab touch and so thoughtful. The beds are also really comfy, we slept like logs. The kitchen and utility room is well stocked and every small detail is thought of. The location is peaceful and secluded, although supermarkets are just a short drive away for grabbing any essentials. We also had a lovely afternoon tea at Stretton Hall Farm nearby - I'd definitely recommend stopping by! The only small downsides was the underfloor heating was a bit too warm, even on the lower setting - we ended up opening the windows and doors a couple of times (not exactly a big issue at all). There was also an occasional sulphur-like smell from the sink and shower drains, but we put this down to the rural location. Overall, we'd not hesitate to visit again in the future and would highly recommend the cottage to others.

      Read more less >

    • Lauren - Verified booking

      Absolutely loved our stay at cherry tree cottage, we were staying with our toddler and there were some toys and crayons left which was handy.

      The cottage was decorated for Christmas which was a nice touch, very festive. The kitchen was very well equipped with everything we might need as well as essentials like salt, pepper, cooking oil, coffee tea etc, there was also enough dishwasher tablets for our stay which is good as usually there is only one supplied. The hosts even supplied plastic cups/dishes/plates and cutlery for our little one. The cottage itself is very lovely and has been done to a high spec, everything looked brand new. My only point to note is that the property is directly on an A road which we didn’t realise when booking and the gate was not secure enough for our dog as she is only small and could get underneath so we had to careful. It was fine though we just made sure she was always on the lead even in the garden. Will be returning next year! :)

      Read more less >

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    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

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