Chat with us, powered by LiveChat

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
Chesterfield 16 miles away

Hunters Lodge at Wildersley Farm,

Belper, Derbyshire, England
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
2 bathrooms 2 bathrooms
 3 dogs welcome  multi-dogs (up to 3)
family friendly family friendly

Hunters Lodge: Luxurious pet-free retreat in Derbyshire's countryside, offering stunning views, hot tub, and open-plan living; sleeps six with three king-size bedrooms, near Belper's heritage sites and Peak District National Park attractions.

ground floor bedroom near local pub
Facilities, Features & Awards:
dishwasher in kitchenmicrowave in kitchenindoor hot tub accessfree WifigardenParking
7 nights from £1076
Next available: 18 Jan - 7 nights
book online online booking
View
Online Booking Available
Viewed 43 times recently.
no booking fee
Chesterfield 8 miles away

The Escape,

Two Dales, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
4 bathrooms 4 bathrooms
no dogs allowed No pets
family friendly family friendly

Sleeps 10 holiday house with warm bubbly outdoor private hot tub and games room, just outside of the Peak District National Park.

ensuite bedroom(s) countryside views over fields and farmlands
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree WifigardenBBQParking
7 nights from £2200
Next available: 06 Dec - 7 nights
book online online booking
View
Online Booking Available
Viewed 27 times recently.
Chesterfield 12 miles away

Field House,

Alfreton, Derbyshire, England
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
1 bathrooms 1 bathroom
 1 dog welcome  1 dog allowed
family friendly family friendly

Field House in Swanwick, Derbyshire is a remarkable, detached holiday home in attractive surroundings.

ground floor bedroom near local pub
Facilities, Features & Awards:
microwave in kitchenfree WifigardenParking
7 nights from £524
Next available: 07 Dec - 3 nights
book online online booking
View
Online Booking Available
Viewed 25 times recently.
Chesterfield 14 miles away

Garden Cottage, Peak District,

Kirk Ireton, Derbyshire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

Delightful one bedroom rural retreat featuring neutral calming tones and a very comfortable interior, ideal for a couple looking to enjoy a tranquil romantic break nestled by the beautiful Derbyshire rolling countryside and within the Peak District National Park.

ensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenfree Wifigardenwood burning stovefireplaceParking
7 nights from £457
Next available: 12 Dec - 7 nights
book online online booking
View
Online Booking Available
Viewed 41 times recently.
no booking fee
Chesterfield 8 miles away

Two Owls Lodge,

Two Dales, Derbyshire, England
sleeps  3 sleeps 3
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

Idyllic sleeps 3 rural retreat in a superb country location and with beautiful views over the Derwent Valley, situated just outside of the Peak District National Park and close to Matlock.

valley views near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifiPatio Gardenwood burning stovefireplaceParking
7 nights from £595
book online online booking
View
Chesterfield 15 miles away

Top Hill Farm Cottage,

Sheffield, South Yorkshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Top Hill Farm Cottage in South Yorkshire offers breathtaking panoramic views, a luxurious hot tub, and spacious open-plan living, sleeps four, ideally located for Peak District exploration; sorry, no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenoutdoor hot tub accessfree WifigardenfireplaceParking
7 nights from £823
Next available: 02 Jan - 7 nights
book online online booking
View
Family-Friendly
Viewed 34 times recently.
Chesterfield 17 miles away

Ebenezer Chapel,

Milford, Derbyshire, England
sleeps  20 sleeps 20
8 bedrooms 8 bedrooms
5 bathrooms 5 bathrooms
 1 dog welcome  1 dog allowed
family friendly family friendly

With a riverside location and river views, this unique chapel conversion in Milford could be the ideal place to holiday with friends or family close to the Peak District, and the on site sauna suite helps to make it a great place to relax and unwind too.

ground floor bedroom river views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchensaunafree Wifigardenwood burning stoveBBQ
7 nights from £1695
Next available: 03 Jan - 7 nights
Special Offer: 09 Jan - 3 nights
Family-Friendly
Viewed 48 times recently.
Chesterfield 18 miles away

Billys Bothy,

Ashbourne, Derbyshire, England
sleeps  16 sleeps 16
6 bedrooms 6 bedrooms
6 bathrooms 6 bathrooms
no dogs allowed No pets
family friendly family friendly

Large award winning holiday cottage set within landscaped gardens, near the Peak District, sleeps up to 16 plus 2 cots.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
gold award winning cottagesmart TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accesssaunafree Wifienclosed gardenwood burning stoveBBQfirepitParking
7 nights from £2430
Next available: 06 Dec - 7 nights
Online Booking Available
Viewed 44 times recently.
no booking fee
Chesterfield 8 miles away

The Haven - Luxury Sheltered Hot Tub & Games Room,

Two Dales, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
4 bathrooms 4 bathrooms
no dogs allowed No pets
family friendly family friendly

No pets 5 bedroom holiday home in a tranquil village setting near Bakewell and the Peak District National Park, with the added luxury of a bubbly outdoor hot tub and games room.

ensuite bedroom(s) countryside views over fields and farmlands
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree Wifienclosed gardenBBQParking
7 nights from £2200
Next available: 06 Dec - 7 nights
book online online booking
View
Online Booking Available
Viewed 21 times recently.
Chesterfield 11 miles away

The Cow Shed,

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

Escape to The Cowshed, a cosy countryside retreat in Derbyshire's Peak District, boasting stunning views, a private hot tub, and accommodation for two, ideal for romantic getaways; sorry, no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
indoor hot tub accessfree WifigardenParking
7 nights from £500
Next available: 30 Jan - 7 nights
book online online booking
View
Chesterfield 9 miles away

The Gatehouse,

Sutton-in-Ashfield, Nottinghamshire, England
sleeps  8 sleeps 8
4 bedrooms 4 bedrooms
2 bathrooms 2 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Escape to The Gatehouse in Teversal, Nottinghamshire, a countryside haven sleeping eight, with stunning garden views, a hot tub, and dog-friendly policy, perfect for exploring the East Midlands' rich heritage and scenic trails.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
microwave in kitchen
7 nights from £1172
Next available: 03 Jan - 7 nights
book online online booking
View
Family-Friendly
Viewed 62 times recently.
no booking fee
Chesterfield 13 miles away

Old Coach House,

Aldwark, Derbyshire, England
sleeps  7 sleeps 7
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
  unlimited  dogs welcome  unlimited dogs welcome
cat friendly cat friendly

Searching for a family cottage in the Peak District National Park? This charming pet-friendly cottage is ideal for family holidays, enjoys an idyllic setting next to fields and should be a hit with the kids with a garden with swings and sandpit where the children can play.

5 (1 reviews)
ground floor bedroom countryside views over fields and farmlands
Facilities, Features & Awards:
gold award winning cottagesmart TVmicrowave in kitchenfree Wifienclosed gardenwood burning stovefireplaceBBQParking
7 nights from £240
Next available: 15 Dec - 5 nights
Chesterfield 15 miles away

Green Barn,

Sheffield, South Yorkshire, England
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
3 bathrooms 3 bathrooms
 2 dogs welcome  2 dogs welcome

Escape to Green Barn in the picturesque Sheffield countryside, a dog-friendly retreat in South Yorkshire near the Peak District, offering stunning views, luxurious amenities, and sleeping 6 guests, with easy access to local attractions.

ground floor bedroom near local pub
Facilities, Features & Awards:
dishwasher in kitchenmicrowave in kitchenindoor hot tub accessfree WifigardenParking
7 nights from £1002
Next available: 02 Jan - 7 nights
book online online booking
View
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 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
* 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