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

29 properties

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Online Booking Available
Viewed 23 times recently.
Price from £1312
Next available 07/03 to 10/03/23
sleeps 4 - 7 guests 4 - 7
3 bedrooms 3
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

3 bedroom Farmstay

Family-friendly and pet-friendly holiday barn set next to stunning open countryside within the Peak District National Park and close to the town of Bakewell, this is a wonderfully relaxing place to stay which offers private use of both a hot tub and a sauna.

Facilities & Features: TVFree WifiGames roomIndoor Hot TubSauna
4 star
Property from Sykes Cottages.
Online Booking Available
Viewed 16 times recently.
Price from £1737
Next available 15/02 to 17/03/23
sleeps 4 - 8 guests 4 - 8
4 bedrooms 4
2 bathrooms 2
no dogs allowed

4 bedroom Barn Conversion

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: TVFree Wifi
5 star
Property from Sykes Cottages.
Online Booking Available
Viewed 49 times recently.
Price from £4900
Next available 19/02 to 24/02/23
sleeps 6 - 18 guests 6 - 18
6 bedrooms 6
5 bathrooms 5
dog-friendly cottage, 1 dog(s) welcome1

6 bedroom Large Country House

6 Bedroom Pet-Friendly Holiday Rental with Indoor Swimming Pool and Outdoor Hot Tub, near Derby and the Peak District National Park The Gatehouse is an ideal location for your next holiday, with plenty to enjoy and explore in the surrounding areas and grassy views.

Facilities & Features: TVFree WifiGames roomOutdoor Hot TubHeated pool
Property from Derbyshire Holidays.
Online Booking Available
Viewed 20 times recently.
Price from £3920
Next available 12/02 to 17/02/23
sleeps 7 - 14 guests 7 - 14
7 bedrooms 7
7 bathrooms 7
dog-friendly cottage, 2 dog(s) welcome2

7 bedroom Large Country House

Welcoming 7 en-suite bedroom holiday lodge with spacious and contemporary furnishings sleeping up to 14 adults (plus 2 children) and boasting a stunning location in the Peak District National Park with spectacular scenery and breath taking views over the Hope Valley.

Facilities & Features: Digital TVFree WifiGames room
Online Booking Available
Viewed 14 times recently.
Price from £1356
Next available 13/03 to 16/03/23
sleeps 4 - 9 guests 4 - 9
4 bedrooms 4
3 bathrooms 3
dog-friendly cottage, 1 dog(s) welcome1

4 bedroom Holiday Farmhouse

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.

Facilities & Features: TVFree WifiGames room
5 star
Property from Sykes Cottages.
Online Booking Available
Viewed 8 times recently.
Price from £536
Next available 09/02 to 16/02/23
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
no dogs allowed

1 bedroom Romantic Retreat

Escape to the country for a romantic break to this 1 bedroom barn conversion on a farm close to Matlock and the Peak District National Park, sorry no pets.

Facilities & Features: TVFree Wifi
5 star
Property from Sykes Cottages.
Family-Friendly
Viewed 48 times recently.
Price from £240
Next available 02/03 to 25/03/23
no booking fee
sleeps 4 - 6 guests 4 - 6
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2

2 bedroom Stone-Built Barn Conversion

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.

Facilities & Features: TVFree Wifi
5 star
Online Booking Available
Viewed 20 times recently.
Price from £660
Next available 25/02 to 09/03/23
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
no dogs allowed

1 bedroom Cottage

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

Facilities & Features: TVFree Wifi
4 star
Property from Sykes Cottages.
Online Booking Available
Viewed 21 times recently.
Price from £653
Next available 17/02 to 03/03/23
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

1 bedroom Romantic Retreat

Good quality one bedroom barn conversion nestled in a rural hamlet within the Peak District National Park, this is a charming pet-friendly holiday home which is located just 7 miles from Bakewell.

Facilities & Features: TVFree Wifi
4 star
Property from Sykes Cottages.
Family-Friendly
Viewed 28 times recently.
Price from £2150
Next available 09/02 to 22/02/23
Special Offer 08/02 to 28/02/23
sleeps 10 - 16 guests 10 - 16
5 bedrooms 5
2 bathrooms 2
no dogs allowed

5 bedroom Large Country House Rental

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

Facilities & Features: Digital TVFree WifiOutdoor Hot Tub
Family-Friendly
Viewed 24 times recently.
Price from £1595
Next available 13/02 to 17/02/23
sleeps 8 - 20 guests 8 - 20
8 bedrooms 8
5 bathrooms 5
dog-friendly cottage, 3 dog(s) welcome3

8 bedroom Unusual Self-Catering

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.

Facilities & Features: Digital TVFree WifiSauna
Property from Derbyshire Holidays.
Family-Friendly
Viewed 53 times recently.
Price from £1495
Next available 13/02 to 24/02/23
sleeps 2 - 22 guests 2 - 22
8 bedrooms 8
5 bathrooms 5
dog-friendly cottage, 2 dog(s) welcome2

8 bedroom Unique Self-Catering Accommodation

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.

Facilities & Features: TVFree WifiSauna
Property from Derbyshire Holidays.
Online Booking Available
Viewed 45 times recently.
Price from £4200
Next available 26/02 to 17/03/23
sleeps 10 - 22 guests 10 - 22
8 bedrooms 8
6 bathrooms 6
dog-friendly cottage, 2 dog(s) welcome2

8 bedroom Large Country House

8 bedroom country house with private swimming pool, hot tub, sauna, beautiful gardens and a BBQ lodge close to Matlock and the Peak District National Park, pet-friendly with 2 dogs welcome.

Facilities & Features: TVFree WifiGames roomOutdoor Hot TubSaunaHeated pool
Property from Derbyshire Holidays.
Online Booking Available
Viewed 20 times recently.
Price from £1599
Next available -
sleeps 6 - 12 guests 6 - 12
6 bedrooms 6
6 bathrooms 6
no dogs allowed

6 bedroom Cottage

A former Bed & Breakfast, the fantastic detached house of Pig-Of-Lead rests at the foot of the village of Bonsall in Derbyshire.

Facilities & Features: TVFree Wifi
3 star
Property from Sykes Cottages.
Online Booking Available
Viewed 31 times recently.
Price from £2100
Next available 09/02 to 03/03/23
sleeps 10 - 20 guests 10 - 20
9 bedrooms 9
5 bathrooms 5
dog-friendly cottage, 2 dog(s) welcome2

9 bedroom Large Country House

Sleeps 20, 9 Bedroom Rural Holiday House with Games Room with Pool Table, near Belper and the Peak District Turpins cottage could be a stunning location for your next holiday, situated on a pretty farm setting, where you can escape from busy city or town life with your friends and family.

Facilities & Features: TVFree WifiGames room
Property from Derbyshire Holidays.
* 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

Book a Chesterfield cottage and look forward to discovering some of the best of Derbyshire on holiday.

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