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The best holiday homes in Chesterfield

Check out our pick of great holiday homes in Chesterfield

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Peak Period Property, hotel in Chesterfield

A recently renovated holiday home set in Chesterfield, Peak Period Property features a garden.

Property was a good location for walking into town and exploring the Peak District. We liked Chesterfield and found some nice restaurants and bars. The lounge and dining room were large enough for us to relax dine and play games as we were a family of four adults, celebrating a birthday.
Scored 9.3
9.3
Rated superb
Superb
13 reviews
Price from
£153.35
1 night, 2 adults
Coxleigh House, hotel in Chesterfield

Offering quiet street views, Coxleigh House is an accommodation situated in Chesterfield, 33 km from Utilita Arena Sheffield and 39 km from Clumber Park.

Second time I have stayed at this place and it’s always been a wonderful experience.
Scored 9.1
9.1
Rated superb
Superb
57 reviews
Price from
£75
1 night, 2 adults
Derbyshire Holiday Cottages, hotel in Holmesfield

Boasting garden views, Derbyshire Holiday Cottages features accommodation with a garden and a balcony, around 15 km from Chatsworth House.

Great communication from host Tracy. Lovely views Lovely and cozy when walked in
Scored 9.4
9.4
Rated superb
Superb
46 reviews
Price from
£103.27
1 night, 2 adults
Acorn Cottage, Ashover, hotel in Ashover

A recently renovated holiday home located in Ashover, Acorn Cottage, Ashover features a garden. With garden views, this accommodation provides a patio.

Perfect, quiet place. Ideal for dogs who hate fireworks. Loved the log fire 🔥
Scored 9.6
9.6
Rated exceptional
Exceptional
9 reviews
Price from
£387.63
1 night, 2 adults
3 Bedroom house, close to woodland, chesterfield and peak District, hotel in Brimington

3 Bedroom house, close to woodland, chesterfield and peak District, a property with a terrace, is set in Brimington, 24 km from Utilita Arena Sheffield, 27 km from Clumber Park, as well as 30 km from...

The accommodation is clean, everything you need is available to use,very quiet area. You can relax after a long trip and activities from Chatsworth House. Good communication with the host and check-in really smoothly.
Scored 8.8
8.8
Rated fabulous
Fabulous
22 reviews
Price from
£97.50
1 night, 2 adults
Kingfisher Lodge, hotel in Froggatt

Offering garden views, Kingfisher Lodge is an accommodation situated in Froggatt, 8.3 km from Chatsworth House and 23 km from Utilita Arena Sheffield.

Great location for walking Superb standard Delicious food at the pub neat Fantastic views Lively hosts
Scored 9.6
9.6
Rated exceptional
Exceptional
230 reviews
Price from
£98
1 night, 2 adults
The Brosterfield Suite - Brosterfield Farm, hotel in Bakewell

The Brosterfield Suite - Brosterfield Farm is situated in Bakewell, 18 km from Buxton Opera House, 30 km from Utilita Arena Sheffield, as well as 45 km from Capesthorne Hall.

Great location, nicely decorated room, really good power shower
Scored 9.0
9.0
Rated superb
Superb
114 reviews
Price from
£103.40
1 night, 2 adults
Church Barn - Private barn perfect for 2 guests stunning location, hotel in Bakewell

Located in Bakewell and only 11 km from Chatsworth House, Church Barn - Private barn perfect for 2 guests stunning location provides accommodation with quiet street views, free WiFi and free private...

Very stylish, clean, comfortable and some nice touches with bits for both us and our dog on arrival. Induction hobs are the future and was great to have that 😊 also there was very good communication before arrival over how to find The Barn and what to expect at the property
Scored 9.6
9.6
Rated exceptional
Exceptional
108 reviews
Price from
£150
1 night, 2 adults
Peak District Romantic Retreat Outdoor Japanese Whirlpool bath, hotel in Stanton in Peak

Boasting air-conditioned accommodation with a patio, Peak District Romantic Retreat Outdoor Japanese Whirlpool bath is set in Stanton in Peak.

The cleanliness and overall layout of the cabin was exceptional combined with the location and views all around us we couldn’t have been more settled and relaxed.
Scored 9.7
9.7
Rated exceptional
Exceptional
28 reviews
Price from
£325
1 night, 2 adults
Hope Terrace, hotel in Matlock

Hope Terrace is located in Matlock, 36 km from Buxton Opera House, 38 km from Alton Towers, and 43 km from Utilita Arena Sheffield.

Fantastic property for two families. Had everything we could possibly need. Bedrooms were plenty big enough, particularly with a travel cot. Spacious kitchen and dining area. The hosts were kind enough to offer us free tickets to the Matlock Baths illuminations and very kindly left a few little Halloween treats for the kids. Very thoughtful and appreciated! Perfect base for exploring the Peak District. Bakewell, Chatsworth House, various fantastic National Trust sites within a relatively short drive away. Matlock 5 minutes down the road with no shortage of restaurants and a great park for the smaller ones. 100% recommend.
Scored 9.7
9.7
Rated exceptional
Exceptional
31 reviews
Price from
£567.15
1 night, 2 adults
All holiday homes in Chesterfield
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Chesterfield this month

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Enjoy breakfast in Chesterfield!

  • Garden Cottage - Ashover Village near Matlock
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 117 reviews

    Offering inner courtyard views, Garden Cottage - Ashover Village near Matlock is an accommodation situated in Chesterfield, 35 km from Utilita Arena Sheffield and 37 km from Clumber Park.

    Warm and cosy. Good facilities. Very friendly owners.

  • Blissful Barrys
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 5 reviews

    Offering a garden and garden view, Blissful Barrys is located in Chesterfield, 24 km from Chatsworth House and 30 km from Clumber Park.

  • Cuckoo Nest
    Breakfast options
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 12 reviews

    Situated 14 km from Chatsworth House, Cuckoo Nest features accommodation with free WiFi and free private parking.

    cosy and private , very clean with excellent facilities

  • SpaPartyHome with Hottub Sauna bbq & Pool Table
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 6 reviews

    Set in Chesterfield, 25 km from Utilita Arena Sheffield, SpaPartyHome with Hottub Sauna bbq & Pool Table provides accommodation with a hot tub.

    All facilities were excellent Great location Clean and spacious

  • Spire Haven
    Breakfast options
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 12 reviews

    Located 19 km from Chatsworth House, Spire Haven provides accommodation with free WiFi and free private parking.

    Modern house, beautifully furnished, very comfortable and well equipped accommodation

  • The Olde Coach House
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 9 reviews

    20 km from Chatsworth House in Chesterfield, The Olde Coach House provides accommodation with access to a hot tub and fitness room. This holiday home offers accommodation with a patio.

    Beautiful character property in great location, lovely and clean.

  • Cedar Holme
    Breakfast options
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 14 reviews

    Situated 17 km from Chatsworth House, Cedar Holme features accommodation with free WiFi and free private parking.

    Very comfortable and clean everything of high quality.

  • The Loft at The George
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 18 reviews

    Located in Chesterfield in the Derbyshire region, The Loft at The George provides accommodation with free WiFi and free private parking.

    Fabulous comfortable warm and cosy! Comfy bed and well equipped!

Save money on holiday homes in Chesterfield – budget options available!

  • Riber View Barn
    Budget options available
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 8 reviews

    Situated 36 km from Utilita Arena Sheffield, 39 km from Buxton Opera House and 40 km from Nottingham Castle, Riber View Barn offers accommodation located in Chesterfield.

    breakfast at Kath's cafe was lovely. staff were friendly

  • The Old Chapel
    Budget options available
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 13 reviews

    The Old Chapel, a property with a garden and barbecue facilities, is situated in Chesterfield, 33 km from Clumber Park, 34 km from Utilita Arena Sheffield, as well as 37 km from Nottingham Castle.

    There was a Christmas Tree and decorations- very nice

  • Woodview Lodge
    Budget options available
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 43 reviews

    Boasting garden views, Woodview Lodge features accommodation with a garden and a patio, around 15 km from Chatsworth House.

    The location was perfect - very close to Chatsworth and two lovely pubs.

  • Little Manor
    Budget options available
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 21 reviews

    Little Manor, a property with a garden, is set in Chesterfield, 24 km from Utilita Arena Sheffield, 27 km from Clumber Park, as well as 30 km from Sherwood Forest.

    The house was lovely and not to far from the peak district

  • Chesterfield Central 2-Bed - Spacious & Sleeps 5
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 8 reviews

    Situated in Chesterfield in the Derbyshire region, Chesterfield Central 2-Bed - Spacious & Sleeps 5 has a terrace. Set 24 km from Utilita Arena Sheffield, the property features a garden.

  • Cedar Cottage
    Budget options available
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 11 reviews

    Situated 20 km from Utilita Arena Sheffield, Cedar Cottage features accommodation with free WiFi and free private parking.

    The cleanliness and the thought put into the facilities provided.

  • Cottage Style 3 bedroom House - Close to City centre & The Peaks
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 7 reviews

    Set in Chesterfield in the Derbyshire region, Cottage Style 3 bedroom House - Close to City centre & The Peaks has a patio.

  • Swallows Barn
    Budget options available
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 5 reviews

    Set in Chesterfield in the Derbyshire region, Swallows Barn offers accommodation with free WiFi and free private parking.

    Area central for visiting places. Beautiful surroundings.

Great access to the city centre! Check these holiday homes in Chesterfield

  • Stables Lodge
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Stables Lodge, a property with a garden, is set in Chesterfield, 28 km from Utilita Arena Sheffield, 35 km from Clumber Park, as well as 40 km from Buxton Opera House.

  • West Barn
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 reviews

    West Barn, a property with a garden, is located in Chesterfield, 30 km from Utilita Arena Sheffield, 35 km from Buxton Opera House, as well as 38 km from Clumber Park.

  • Harry's Lodge
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set 14 km from Chatsworth House, Harry's Lodge offers accommodation with free WiFi and free private parking.

  • Cherry Tree Cottage
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Boasting a hot tub, Cherry Tree Cottage is set in Chesterfield. The property is around 31 km from Utilita Arena Sheffield, 36 km from Buxton Opera House and 38 km from Clumber Park.

  • Greenwell Cottage
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

    Greenwell Cottage offers a hot tub and free private parking, and is within 20 km of Clumber Park and 22 km of Sherwood Forest. The 5-star holiday home is 33 km from Chatsworth House.

  • The Tower
    Central location
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Located 17 km from Clumber Park, The Tower provides accommodation with free WiFi and free private parking.

  • The Old Stables
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    The Old Stables, a property with a garden, is located in Chesterfield, 34 km from Utilita Arena Sheffield, 38 km from Clumber Park, as well as 40 km from Buxton Opera House.

  • Tuliptree
    Central location
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    Tuliptree, a property with a garden, is set in Chesterfield, 35 km from Utilita Arena Sheffield, 37 km from Clumber Park, as well as 41 km from Buxton Opera House.

  • Number 26 Van Dyk Village
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    Set in Chesterfield and only 19 km from Clumber Park, Number 26 Van Dyk Village offers accommodation with quiet street views, free WiFi and free private parking. 30 km from Sherwood Forest and 34 km...

  • Peak Period Property
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 13 reviews

    A recently renovated holiday home set in Chesterfield, Peak Period Property features a garden.

    Excellent space, facilities and value. Really responsive host

  • Overton
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 3 reviews

    Overton is situated in Chesterfield, 22 km from Utilita Arena Sheffield, 34 km from Clumber Park, as well as 41 km from Buxton Opera House.

  • 1 Bed in Barlow 40971
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Situated in Chesterfield and only 15 km from Chatsworth House, 1 Bed in Barlow 40971 features accommodation with garden views, free WiFi and free private parking.

  • Woodthorpe Cruck Cottage
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 4 reviews

    Boasting a hot tub, Woodthorpe Cruck Cottage is set in Chesterfield. Complimentary WiFi is available throughout the property and private parking is available on site.

  • Morden house close to City centre & The Peaks
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 4 reviews

    Offering a garden and garden view, Morden house close to City centre & The Peaks is located in Chesterfield, 21 km from Chatsworth House and 22 km from Utilita Arena Sheffield.

  • Manor House
    Central location
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 5 reviews

    Boasting a hot tub, Manor House is set in Chesterfield. The property is located 26 km from Utilita Arena Sheffield, 29 km from Clumber Park and 38 km from Sherwood Forest.

  • Wingfield Lodge - Near Clay Cross
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 3 reviews

    Offering a garden and quiet street view, Wingfield Lodge - Near Clay Cross is set in Chesterfield, 28 km from Clumber Park and 35 km from Sherwood Forest.

  • Large 2-Bed House Derbyshire off Chatsworth rd
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 23 reviews

    Situated in Chesterfield in the Derbyshire region, Large 2-Bed House Derbyshire off Chatsworth rd has a patio.

    Excellent location. Very spacious. Sitting room was big.

  • Moor Farm Cottage
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 1 review

    Located in Chesterfield in the Derbyshire region, Moor Farm Cottage provides accommodation with free WiFi and free private parking.

  • Appletree Cottage
    Scored 7.4
    7.4
    Rated good
    Good
     · 9 reviews

    Set 25 km from Sherwood Forest, 28 km from Utilita Arena Sheffield and 31 km from Chatsworth House, Appletree Cottage offers accommodation situated in Chesterfield.

    Lovely homely cottage. Great rooms, decor and comfort. Wi-fi great.

  • Vernon Cottage
    Scored 6.7
    6.7
    Rated pleasant
    Pleasant
     · 3 reviews

    Offering a terrace and garden view, Vernon Cottage is situated in Chesterfield, 21 km from Utilita Arena Sheffield and 35 km from Clumber Park.

  • DotSpaPartyHomeDotCom
    Scored 6.5
    6.5
    Rated pleasant
    Pleasant
     · 2 reviews

    Situated in Chesterfield in the Derbyshire region, DotSpaPartyHomeDotCom features accommodation with free WiFi and free private parking, as well as access to a sauna.

  • Dryden House
    Central location
    Scored 6.0
    6.0
    Rated pleasant
    Pleasant
     · 3 reviews

    Offering a garden and garden view, Dryden House is located in Chesterfield, 25 km from Utilita Arena Sheffield and 32 km from Clumber Park.

  • Temperance Croft
    Scored 1.0
    1.0
    Rated very poor
    Bad
     · 1 review

    Situated in Chesterfield in the Derbyshire region, Temperance Croft features accommodation with free WiFi and free private parking.

  • Casa Vault
    Central location

    Offering quiet street views, Casa Vault is an accommodation situated in Chesterfield, 25 km from Utilita Arena Sheffield and 32 km from Clumber Park.

  • Walton Cottage - 2 Beds - Sleeps 4 - Pet Friendly

    Set in Chesterfield and only 17 km from Chatsworth House, Walton Cottage - 2 Beds - Sleeps 4 - Pet Friendly offers accommodation with garden views, free WiFi and free private parking.

  • Byron House
    Central location

    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.

  • Hady House
    Central location

    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.

  • The Lily Pad
    Central location

    The Lily Pad, a property with a garden, is located in Chesterfield, 24 km from Utilita Arena Sheffield, 34 km from Clumber Park, as well as 38 km from Buxton Opera House.

FAQ about holiday homes in Chesterfield

Holiday homes that guests love in Chesterfield

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  • Avg. price/night: £140
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2,798 reviews
    Great Rooms Spacious Very Clean Well Equipped The Gym!!! Could benefit from upgrading the running machine perhaps Great Breakfast Selection Very helpful and friendly staff
    Andrea
    Solo traveller
  • Avg. price/night: £107.10
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 2,039 reviews
    very clean and nice breakfast
    charles
    Young couple
  • Avg. price/night: £145
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 1,751 reviews
    Great location, very clean, amazing staff, incredible food. What more could you ask for.
    Jessica
    Family with young children
  • Avg. price/night: £39.95
    Scored 7.8
    7.8
    Rated good
    Good
     · 2,174 reviews
    Good value staff was amazing so pleasant would definitely stop again Also rooms was very clean and everything you need for a good stay thank you to all staff
    Jeanette
    Solo traveller
  • Avg. price/night: £100
    Scored 8.1
    8.1
    Rated very good
    Very good
     · 1,301 reviews
    Very good staff I also have very sensitive stomach and every meal was cooked perfectly and I had no stomach issues with my condition this means very clean high standards kitchen
    Richard
    Solo traveller
  • Avg. price/night: £100
    Scored 8.1
    8.1
    Rated very good
    Very good
     · 1,301 reviews
    The room was very clean and all the staff were polite, friendly & professional. The room wi-fi speed was excellent too. Food was very good, especially the cooked breakfasts. A perfect location for day trips to local attractions in the Derbyshire Dales area and beyond.
    Nick
    Family with young children
  • Avg. price/night: £73.13
    Scored 7.9
    7.9
    Rated good
    Good
     · 620 reviews
    Room very clean and tidy , food was also very good
    michael
    Young couple
  • Avg. price/night: £142
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 87 reviews
    Very clean. Really nice finish on decor. Good parking at the front. All on one level except for one tiny step. Walkable to town centre but also good bus links. Several good convenience stores nearby. Responsive host.
    Kim
    Young couple
  • Avg. price/night: £140
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2,798 reviews
    Room very clean and spacious bed very comfortable, lightning could have been better when getting hair and makeup done was quite dime but not a big issue
    T
    Turner
    Solo traveller
  • Avg. price/night: £140
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2,798 reviews
    Very clean, ultra modern and relatively quiet.
    benedict
    Solo traveller

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