A stone path winding through a valley with a sunset in the background.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chesterfield holiday rentals

A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

1. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
The price is RM2,025
RM2,430 total
includes taxes & fees
2 Nov - 3 Nov
Carr House Farm
A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

2. 2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Property is self catering house at edge of the town. Spacious and decent kitchen. Road quiet (liked that) and easy access to nature reserve/countryside walks. Parking a bit of an issue but didn’t detract from our stay. "
United Kingdom
Philip
2bed - Garden-pets-freeparking-m1connections
A stone building with a water wheel and a staircase.

3. Little Mill

Little Mill
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Lovely little cottage in a beautiful setting. Great walks around. Bed comfortable and lovely warm shower. The welcome package was very helpful as I arrived late on Sunday and forgot the English shops closed early!"
United Kingdom
Rona
The price is RM1,519
RM1,822 total
includes taxes & fees
1 Nov - 2 Nov
Little Mill
A hot tub under a wooden pergola with a stone wall and greenery in the background.

4. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is RM2,972
RM3,567 total
includes taxes & fees
22 Nov - 23 Nov
Cherry Tree Cottage
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

5. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is RM1,802
RM2,162 total
includes taxes & fees
30 Oct - 31 Oct
Cedar Cottage
A sunlit room with a large window, a sofa, a table, and a potted plant.

6. Overton

Overton
3.0 star property
Chesterfield
The price is RM2,615
RM3,138 total
includes taxes & fees
21 Nov - 22 Nov
Overton
A rural road with stone walls and a stone building with a sign.

7. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is RM1,593
RM1,912 total
includes taxes & fees
2 Nov - 3 Nov
Riber View Barn
A cozy cabin-style interior with a kitchen, dining area, and seating space.

8. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is RM2,188
RM2,625 total
includes taxes & fees
31 Oct - 1 Nov
Thorntree Lodge
A rural landscape with a stone wall, greenery, and a clear sky.

9. Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"The location is fine and the view beautiful. The owners were very helpful when needed. A most enjoyable stay."
Australia
Ian
The price is RM2,174
RM2,174 total
includes taxes & fees
8 Nov - 9 Nov
Shire Cottage at Top Butterley Farm
A four-poster bed with a wooden frame and a canopy, a chandelier, a window with floral curtains, and a radiator.

10. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is RM2,578
RM3,093 total
includes taxes & fees
9 Nov - 10 Nov
The Tack Room Cottage
A hot tub in a backyard with a stone wall and a grassy lawn.

11. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
6.0 out of 10, (1 review)
"I'll start with the good. Location is nice and peaceful. The bungalow is well laid out and there is plenty of room. Facilities inside the bungalow are good. Cooking and dining implements all there and lots of space. Bedrooms are nice and have plenty of storage for a short break. The garden is well maintained and enclosed although there is only 2 comfortable chairs and no swing or sofa. Parking around the back of the property is the best but you are encouraged to park at the front tucked...
United Kingdom
June
The price is RM2,815
RM3,377 total
includes taxes & fees
1 Nov - 2 Nov
Wigley Farm House Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

12. The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"Out in the country but easy access to main routes. Nice and quiet. Very clean and well equipped. Nice owners. "
United Kingdom
Mark
The price is RM2,073
RM2,073 total
includes taxes & fees
4 Nov - 5 Nov
The Old Chapel
A wooden deck with outdoor seating and a glass door leading to a covered area.

13. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is RM2,345
RM2,815 total
includes taxes & fees
1 Nov - 2 Nov
Harry's Lodge
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

14. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is RM2,787
RM3,344 total
includes taxes & fees
6 Nov - 7 Nov
Swallows Barn
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

15. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
Cherry Tree Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Four Points Flex by Sheraton Nottingham

Four Points Flex by Sheraton Nottingham

8/10 Good
"The hotel was a pleasant surprise , but the underground parking not quite so . Not an ideal location for a lone person, especially in the dark . The rooms, although very clean and containing everything you need for a short stay,were a little on the small side . Special mention to the chamber maids ,who were very friendly and very helpful.The car park location and the size of the rooms aside, a very pleasant stay and good value for money, in a perfect location.....next to the castle !"
simon 1-night trip
Posted 1 hour ago
Four Points Flex by Sheraton Nottingham

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Clay Cross Active, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Chesterfield has a good selection of top-notch restaurants and lively bars. Make sure you have time to check out the churches and parks during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Old Nags Head: This holiday home rental outside of Chesterfield comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave and kitchenware.

How many holiday rentals will I find in Chesterfield?

With 43 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesterfield stay.

What can I see and do in Chesterfield?

Enjoy the outdoors at Peak District National Park and Queen's Park, or simply take in cultural attractions like Barrow Hill Roundhouse Railway Centre and Hotel Van Dyk Theater. Chesterfield Market and Bolsover Castle are other places to visit while you're in town.

What are holiday rentals like in Chesterfield?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family getaway.