A sign indicating visitor mooring with a 2-day limit, a canal, and a grassy bank with trees in the background.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chesterfield holiday rentals

Private kitchen

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is RM414
RM629 total
includes taxes & fees
12 Oct - 13 Oct
Commuters Getaway Chesterfield
Living area

2. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is RM2,044
RM2,453 total
includes taxes & fees
11 Oct - 12 Oct
Carr House Farm
Terrace/patio

3. 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
The price is RM414
RM629 total
includes taxes & fees
24 Sept - 25 Sept
2bed - Garden-pets-freeparking-m1connections
Exterior

4. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is RM1,527
RM1,832 total
includes taxes & fees
24 Sept - 25 Sept
Little Mill
Private kitchen

5. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is RM556
RM693 total
includes taxes & fees
12 Oct - 13 Oct
a Quiet Semi Rural Property Located in Bolsover
Living area

6. Overton

Overton
2.0 star property
Chesterfield
The price is RM2,628
RM3,154 total
includes taxes & fees
12 Oct - 13 Oct
Overton
Exterior

7. 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 RM2,093
RM2,093 total
includes taxes & fees
26 Sept - 27 Sept
The Old Chapel
Room

8. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is RM1,819
RM2,183 total
includes taxes & fees
2 Oct - 3 Oct
Cedar Cottage
Terrace/patio

9. 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 RM2,988
RM3,586 total
includes taxes & fees
11 Oct - 12 Oct
Cherry Tree Cottage
Exterior

10. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is RM1,608
RM1,929 total
includes taxes & fees
26 Sept - 27 Sept
Riber View Barn
Outdoor spa tub

11. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is RM2,829
RM3,395 total
includes taxes & fees
28 Sept - 29 Sept
Wigley Farm House Cottage
Private kitchen

12. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is RM2,199
RM2,639 total
includes taxes & fees
12 Oct - 13 Oct
Thorntree Lodge
Private kitchen

13. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is RM1,533
RM1,839 total
includes taxes & fees
26 Sept - 27 Sept
Cuckoo Nest
Property grounds

14. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is RM2,367
RM2,841 total
includes taxes & fees
2 Oct - 3 Oct
Harry's Lodge
Living area

15. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is RM3,033
RM3,640 total
includes taxes & fees
11 Oct - 12 Oct
The Cottage
Property grounds

16. Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage
3.5 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is RM2,801
RM3,361 total
includes taxes & fees
24 Sept - 25 Sept
Woodthorpe Cruck Cottage
Interior

17. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
Interior

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is RM2,588
RM3,105 total
includes taxes & fees
18 Sept - 19 Sept
The Loft at The George
Property grounds

19. 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 RM1,868
RM1,868 total
includes taxes & fees
1 Oct - 2 Oct
Shire Cottage at Top Butterley Farm
Garden

20. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The Tack Room Cottage
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

Mercure Nottingham Sherwood Hotel

Mercure Nottingham Sherwood Hotel

8/10 Good
"Very enjoyable stay, nice modern hotel and within walking distance of the city centre."
Paul 1-night trip
Posted 7 hours ago
Mercure Nottingham Sherwood Hotel

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:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

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 45 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.