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Chesterfield, self-catering holiday cottages, barns, rural retreats and lodges to rent in Derbyshire, England

Showing all properties across the UK. Select a destination from the list to refine your search.
27 holiday rentals
Online Booking Available
Viewed 44 times recently.
Chesterfield 13 miles away

Ploughman's Cottage,

Mansfield, Nottinghamshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Comfortable 2 bedroom country cottage nestled in 3 acres of tranquil gardens, discover the best of Nottinghamshire close by with day trips to the riverside town of Newark-on-Trent, Clipstone Forest and Sherwood Forest to name just a few attractions.

ground floor bedroom garden views
Facilities, Features & Awards:
gold award winning cottageTVdishwasher in kitchenmicrowave in kitchenfree WifigardenParking
Sorry, this owner/agency has not provided availability information.
7 nights from £625
book online online booking
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Family-Friendly
Viewed 37 times recently.
Chesterfield 12 miles away

Agricola House,

Wirksworth, Derbyshire, England
sleeps  14 sleeps 14
7 bedrooms 7 bedrooms
5 bathrooms 5 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Award winning, stylish 7 bedroom, 5 bathroom holiday house with cinema room, games console for fun times and relaxing wellness sauna, set in Wirksworth, close to the Peak District National Park.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomsaunafree Wifienclosed gardenBBQParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £4395
Next available: 06 Dec - 7 nights
Family-Friendly
Viewed 33 times recently.
Chesterfield 15 miles away

Clusters Chapel,

Belper, Derbyshire, England
sleeps  20 sleeps 20
8 bedrooms 8 bedrooms
5 bathrooms 5 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

Unique 8 bedroom self-catering chapel in Belper, ideal for groups of friends and family, with a sauna suite for relaxation and close to the Peak District National Park.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchensaunafree Wifienclosed gardenwood burning stoveBBQParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1595
Next available: 06 Dec - 6 nights
Special Offer: 30 Dec - 3 nights
Family-Friendly
Viewed 24 times recently.
Chesterfield 17 miles away

Hillside Croft,

Biggin, Ashbourne, Derbyshire, England
sleeps  16 sleeps 16
5 bedrooms 5 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

5 bedroom large holiday house with private hot tub, set on edge of Peak District National Park, close to both Ashbourne and Carsington Water.

ensuite bedroom(s) garden views
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchenoutdoor hot tub accessfree Wifienclosed gardenwood burning stovefireplaceBBQfirepitParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £2150
Next available: 06 Dec - 7 nights
Online Booking Available
Viewed 33 times recently.
Chesterfield 16 miles away

Orchard View Dogs-Welcome Cottage, Peak District National Park,

Parwich, Derbyshire, England
sleeps  9 sleeps 9
4 bedrooms 4 bedrooms
3 bathrooms 3 bathrooms
 1 dog welcome  1 dog allowed
family friendly family friendly

Idyllic 4 bedroom English country cottage with exposed wooden beams, wood-burning stove and a very comfortable interior and a pet-friendly policy, also features a romantic four poster bed in one of the bedrooms, as well as a superb location within the Peak District National Park and a Wendy House for keeping younger visitors entertained.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stovefireplaceParking
7 nights from £657
Next available: 06 Dec - 7 nights
book online online booking
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Online Booking Available
Viewed 38 times recently.
Chesterfield 18 miles away

Church Barn, Peak District ,

Fenny Bentley, Derbyshire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets

Romantic barn conversion with tranquil views, set in the Peak District National Park, close to Ashbourne, the Tissington Trail and Dovedale.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenfree Wifigardenwood burning stoveParking
7 nights from £359
Next available: 06 Dec - 7 nights
book online online booking
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Manor House,

Chesterfield, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
5 bathrooms 5 bathrooms
no dogs allowed No pets
family friendly family friendly

Discover luxurious living at Manor House, a dog-friendly, detached cottage in Chesterfield, Derbyshire, sleeping ten with a private gym, woodburning stove, and children's play area; perfect for exploring the stunning Peak District's natural beauty.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenfireplaceParking
7 nights from £1752
Next available: 08 Dec - 4 nights
book online online booking
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Chesterfield 18 miles away

Midfeather Cottage,

Edale, Derbyshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

Nestled in Derbyshire's stunning Peak District, this charming, dog-friendly stone barn sleeps 4, offering breathtaking countryside views, original features, and a shared paddock, just a stroll from Edale village and the Pennine Way.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenfree WifigardenParking
7 nights from £476
Next available: 06 Dec - 7 nights
book online online booking
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Chesterfield 11 miles away

The Malthouse,

Matlock, Derbyshire, England
sleeps  18 sleeps 18
9 bedrooms 9 bedrooms
6 bathrooms 6 bathrooms
no dogs allowed No pets
family friendly family friendly

Discover The Malthouse in Cromford, a stunning Grade II listed mill conversion in Derbyshire's Peak District, offering scenic views, luxurious interiors, space for 18 guests, and a unique historic charm, sorry no pets.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenBBQParking
7 nights from £2209
Next available: 08 Dec - 3 nights
book online online booking
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Online Booking Available
Viewed 23 times recently.
Chesterfield 11 miles away

Cow Barn, Peak District National Park,

Alport, Derbyshire, England
sleeps  8 sleeps 8
4 bedrooms 4 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

This beautiful high quality 4 bedroom barn conversion lies within the gorgeous Peak District National Park and boasts a high quality interior and wonderful views over the surrounding Derbyshire countryside.

Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree Wifigardenwood burning stovefireplaceParking
7 nights from £813
Next available: 30 Jan - 7 nights
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Chesterfield 11 miles away

Winster Hall,

Matlock, Derbyshire, England
sleeps  10 sleeps 10
7 bedrooms 7 bedrooms
5 bathrooms 5 bathrooms
 dog-friendly cottage
family friendly family friendly

Winster Hall in Derbyshire's Peak District is a dog-friendly, Grade II listed retreat sleeping 16, featuring original architectural beauty, expansive gardens, and convenient access to Matlock and Bakewell, with captivating village street views.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenfireplaceBBQParking
7 nights from £2278
Next available: 16 Jan - 7 nights
book online online booking
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Online Booking Available
Viewed 22 times recently.
Chesterfield 15 miles away

Lees Farm,

Buxton, Derbyshire, England
sleeps  10 sleeps 10
4 bedrooms 4 bedrooms
2 bathrooms 2 bathrooms
 dog-friendly cottage
family friendly family friendly

Experience rustic charm at this dog-friendly, meticulously restored stone farmhouse in High Peak, Derbyshire, offering breathtaking Monsal Valley views, a cosy wood burner, and sleeping up to 8 guests, just perfect for countryside escapes.

ground floor bedroom near local pub
Facilities, Features & Awards:
free Wifigardenfireplace
7 nights from £834
Next available: 06 Dec - 6 nights
book online online booking
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* Price quoted is not inclusive of any applicable booking fees or local charges.

Book a Chesterfield holiday cottage and look forward to discovering some of the best of Derbyshire on a self-catering break.  This charming market town is home to a good selection of shops, cafes, eateries and plenty of history too!  Surrounded by stunning countryside, this attractive town is just 5 miles from the amazing landscape of the Peak District National Park and is very well placed for an active holiday discovering this scenic area.  A holiday in the Peak District will particularly appeal to holidaymakers who love outdoor pursuits and exploring the great outdoors.

The Peak District National Park is a great area to enjoy walking, hiking and wildlife watching.   For holidaymakers who enjoy cycling, the Monsal Trail offers excellent traffic-free cycling and is just 15 miles from Chesterfield.

Another great family day out can be enjoyed at the Heights of Abraham where there are cable cars, stunning views and ample natural beauty to discover.

Also within reach for day trips (18 miles from Chesterfield), is Carsington Water, where a vast choice of outdoor activities can be enjoyed; from cycling by the lake, to fishing, watersports, and bird watching.

If you want to enjoy time in the city for shopping, dining out or city attractions, then you have plenty of choice too!  Sheffield is just 13 miles from Chesterfield, Nottingham 26 miles away and Derby is 29 miles away.

Whether you are looking to book accommodation for a getaway with friends, your partner or your family,  we hope you have your best holiday yet in this part of Derbyshire.


About Cottage Breaks in Chesterfield

Whether you choose to book a holiday cottage in Chesterfield, an apartment, a lodge or another type of self-catering holiday accommodation, we hope you have your best holiday yet in Derbyshire.

Frequently Asked Questions about Chesterfield

The best places to stay depend on your preferences, interests and the type of accommodation that best suits you. Country Cottages Online features a great selection of good quality rentals.
See our selection of pet-friendly rentals in Chesterfield, or use the filters to refine your search.
See our selection of lodges and cabins in Chesterfield, Derbyshire.
Read the description of Chesterfield to find out ideas and tips on the best things to see and do. Also see our area guides for more information on what Derbyshire has to offer for holidaymakers.

Chesterfield Holiday Rental Searches