Chat with us, powered by LiveChat

Luxury cottages in Chesterfield, Derbyshire, England

Showing all properties across the UK. Select a destination from the list to refine your search.
15 holiday rentals
Family-Friendly
Viewed 34 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: 16 Dec - 4 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
Online Booking Available
Viewed 12 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 37 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: 16 Dec - 4 nights
Online Booking Available
Viewed 16 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: 16 Dec - 4 nights
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
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: 11 Jan - 7 nights
book online online booking
View
Online Booking Available
Viewed 27 times recently.
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
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £2200
Next available: 03 Jan - 7 nights
book online online booking
View
Online Booking Available
Viewed 27 times recently.
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
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £595
book online online booking
View
Family-Friendly
Viewed 12 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
Sorry, this owner/agency has not provided availability information.
7 nights from £4395

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 £2038
Next available: 16 Dec - 3 nights
book online online booking
View
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
View
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 £2177
Next available: 16 Dec - 3 nights
book online online booking
View
Online Booking Available
Viewed 18 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 £821
Next available: 30 Jan - 7 nights
book online online booking
View
* Price quoted is not inclusive of any applicable booking fees or local charges.

The luxury country cottages that we currently have on our books for self catering stays in Chesterfield are shown below. If no suitable 5 star cottages in Chesterfield are available, you may wish to use the Cottage Search to find luxury country cottages in Derbyshire or England and enable you to enter your own pre-requisites, especially if you you have specific requirements such as luxury pet friendly self catering, or cottages with facilities for the disabled.

Depending on the reason for your trip, you may be open to alternative locations other than Chesterfield. We are fortunate to be blessed with many lovely places for holidays in England offering additional options.

Good comfortable accommodation is only one component of your self catering holiday. It always helps to be prepared and know about interesting places to visit in Chesterfield and visitor attractions within easy driving distance of Chesterfield. Your hosts should have a welcome folder with details of the best restaurants in Chesterfield and other useful local information.

If you don't possess a SatNav, Google Maps are helpful in providing directions from one postcode to another with fairly accurate driving times and distances. Do talk to the cottage owner in advance about local landmarks and directions to look out for when you arrive in Chesterfield, especially if the cottage is a little outside the town and you think you may arrive late. Holiday cottages tucked away in country lanes can be difficult to find when it's dark and there is no one about to ask.

All of our luxury cottages in Chesterfield are of the highest standards and you can expect comfortable attractive self catering accommodation and a warm welcome on arrival.

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.

Chesterfield Holiday Rental Searches