A historic building with black and white timber framing, a prominent clock tower, and a pointed spire in the background.

Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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 S$198
includes taxes & fees
1 Sept - 2 Sept
Commuters Getaway Chesterfield
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

2. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is S$576
includes taxes & fees
7 Aug - 8 Aug
Cuckoo Nest
Fridge, microwave, oven, stovetop

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 S$218
includes taxes & fees
4 Aug - 5 Aug
a Quiet Semi Rural Property Located in Bolsover
Property grounds

4. 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 S$584
includes taxes & fees
7 Aug - 8 Aug
Shire Cottage at Top Butterley Farm
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 S$189
includes taxes & fees
12 Aug - 13 Aug
2bed - Garden-pets-freeparking-m1connections
Outdoor spa tub

6. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is S$1,067
includes taxes & fees
7 Aug - 8 Aug
Wigley Farm House Cottage
Exterior

7. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is S$580
includes taxes & fees
6 Aug - 7 Aug
Riber View Barn
3 bedrooms, free WiFi, individually decorated, individually furnished

8. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is S$683
includes taxes & fees
7 Aug - 8 Aug
Cedar Cottage
Fireplace

9. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is S$1,090
includes taxes & fees
14 Aug - 15 Aug
The Cottage
Garden

10. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is S$1,368
includes taxes & fees
30 Aug - 31 Aug
The Tack Room Cottage
Living room

11. The Loft

The Loft
3.5 star property
Chesterfield
The price is S$1,102
includes taxes & fees
30 Aug - 31 Aug
The Loft
Outdoor dining

12. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is S$1,079
includes taxes & fees
4 Aug - 5 Aug
Moor Farm Cottage
Property grounds

13. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is S$891
includes taxes & fees
13 Aug - 14 Aug
Harry's Lodge
Living area

14. Overton

Overton
2.0 star property
Chesterfield
The price is S$993
includes taxes & fees
31 Aug - 1 Sept
Overton
Private kitchen

15. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is S$831
includes taxes & fees
12 Aug - 13 Aug
Thorntree Lodge
Interior

16. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is S$974
includes taxes & fees
10 Aug - 11 Aug
The Loft at The George
Terrace/patio

17. 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 S$1,127
includes taxes & fees
18 Aug - 19 Aug
Cherry Tree Cottage
Property grounds

18. 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 S$1,080
includes taxes & fees
31 Aug - 1 Sept
Woodthorpe Cruck Cottage
Dining

19. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is S$3,523
includes taxes & fees
1 Sept - 2 Sept
Cherry Tree Farm
Interior

20. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is S$1,422
includes taxes & fees
1 Sept - 2 Sept
Swallows Barn
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

Sandman Signature Sheffield Quays Hotel

Sandman Signature Sheffield Quays Hotel

10/10 Excellent
"Great place pool etc kids loved would stay again xxx"
Kath 2-night trip
Posted 2 hours ago
Sandman Signature Sheffield Quays 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 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.