The tow path on the Chesterfield canal on a bright sunny day

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chesterfield holiday rentals

House | 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 2.662.990 ₫
4.042.849 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Commuters Getaway Chesterfield
Living area

2. Overton

Overton
2.0 star property
Chesterfield
The price is 16.894.039 ₫
20.272.847 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Overton
Private kitchen

3. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is 3.571.913 ₫
4.454.477 ₫ total
includes taxes & fees
11 Sept - 12 Sept
a Quiet Semi Rural Property Located in Bolsover
Terrace/patio

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 19.204.592 ₫
23.045.510 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Cherry Tree Cottage
Terrace/patio

5. 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 2.662.990 ₫
4.042.849 ₫ total
includes taxes & fees
8 Sept - 9 Sept
2bed - Garden-pets-freeparking-m1connections
Room

6. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
Carr House Farm
Cottage | Interior

7. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is 30.654.271 ₫
36.785.266 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Swallows Barn
Dining

8. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
Cherry Tree Farm
Outdoor dining

9. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is 9.812.346 ₫
11.774.815 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Little Mill
Property grounds

10. 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 18.004.305 ₫
21.605.166 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Woodthorpe Cruck Cottage
Cottage | Outdoor dining

11. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
Moor Farm Cottage
Cottage | Outdoor spa tub

12. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
Wigley Farm House Cottage
Living area

13. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is 23.387.945 ₫
28.065.534 ₫ total
includes taxes & fees
13 Sept - 14 Sept
The Cottage
Cottage | Exterior

14. 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 13.395.203 ₫
13.395.203 ₫ total
includes taxes & fees
26 Sept - 27 Sept
The Old Chapel
Cottage

15. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is 11.642.784 ₫
13.971.341 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Cedar Cottage
Garden

16. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is 16.653.982 ₫
19.984.778 ₫ total
includes taxes & fees
4 Sept - 5 Sept
The Tack Room Cottage
Cottage | Property grounds

17. 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 11.954.858 ₫
11.954.858 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Shire Cottage at Top Butterley Farm
Cottage | Interior

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is 16.563.960 ₫
19.876.752 ₫ total
includes taxes & fees
6 Sept - 7 Sept
The Loft at The George
Cottage

19. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is 21.455.130 ₫
25.746.156 ₫ total
includes taxes & fees
4 Sept - 5 Sept
The Old Stables
Cottage | Private kitchen

20. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
Thorntree Lodge
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

Leopold Hotel

Leopold Hotel

10/10 Excellent
"It's the best hotel in Sheffield the staff was so welcoming, friendly, ect the breakfast was really nice and plenty to choose from, the room was lovely and clean plenty of room and it had an homely feeling to it, I enjoyed it that much I didn't want to go back home x"
Jenny 5-night trip
Posted 3 hours ago
Leopold Hotel

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.

How many holiday rentals will I find in Chesterfield?

With 44 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. Bolsover Castle and Hardwick Hall 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.