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

Search Holiday Rentals in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chesterfield holiday rentals

House | Private kitchen | Fridge, microwave, oven, stovetop

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is 2.687.975 ₫
4.080.781 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Commuters Getaway Chesterfield
Garden

2. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is 16.810.237 ₫
20.172.284 ₫ total
includes taxes & fees
22 Sept - 23 Sept
The Tack Room Cottage
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 3.605.426 ₫
4.496.271 ₫ total
includes taxes & fees
31 Aug - 1 Sept
a Quiet Semi Rural Property Located in Bolsover
Cottage | 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 12.067.024 ₫
12.067.024 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Shire Cottage at Top Butterley Farm
Outdoor dining

5. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is 9.904.410 ₫
11.885.292 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Little Mill
3 bedrooms, free WiFi, individually decorated, individually furnished

6. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is 13.205.880 ₫
15.847.056 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Carr House Farm
Property grounds

7. 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 18.173.230 ₫
21.807.876 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Woodthorpe Cruck Cottage
Cottage | Outdoor dining

8. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is 18.566.983 ₫
22.280.380 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Moor Farm Cottage
Cottage | 3 bedrooms, free WiFi, individually decorated, individually furnished

9. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
Cedar Cottage
Cottage | Outdoor spa tub

10. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is 18.354.962 ₫
22.025.954 ₫ total
includes taxes & fees
12 Sept - 13 Sept
Wigley Farm House Cottage
Cottage | 4 bedrooms, free WiFi, individually decorated, individually furnished

11. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is 21.656.432 ₫
25.987.718 ₫ total
includes taxes & fees
31 Aug - 1 Sept
The Old Stables
Terrace/patio

12. 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 2.687.975 ₫
4.080.781 ₫ total
includes taxes & fees
1 Sept - 2 Sept
2bed - Garden-pets-freeparking-m1connections
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

13. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is 9.904.410 ₫
11.885.292 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Cuckoo Nest
Fireplace

14. The Cottage

The Cottage
3.0 star property
Chesterfield
The Cottage
Cottage | Interior

15. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is 24.409.142 ₫
29.290.970 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Swallows Barn
Cottage | Living room | TV

16. The Loft

The Loft
3.5 star property
Chesterfield
The Loft
Dining

17. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is 47.986.947 ₫
57.584.194 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Cherry Tree Farm
Cottage | Interior

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is 16.719.371 ₫
20.063.245 ₫ total
includes taxes & fees
31 Aug - 1 Sept
The Loft at The George
Terrace/patio

19. 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 19.384.778 ₫
23.261.734 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Cherry Tree Cottage
Living area

20. Overton

Overton
2.0 star property
Chesterfield
The price is 17.052.547 ₫
20.463.056 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Overton
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Leonardo Hotel Sheffield

Leonardo Hotel Sheffield

10/10 Excellent
"The hotel was clean and tidy, the beds were particularly comfortable as well. We paid for breakfast both days we were there, while it wasn't amazing it still filled a hole to keep us going. Parking was the biggest issue really, £12 for overnight each day was expensive, Overall great for the price we paid and the staff were all friendly, helpful and polite"
Shannon 2-night trip
Posted 5 hours ago
Leonardo Hotel Sheffield

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. 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.