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

Chesterfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterfield holiday rentals

1. 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

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is S$2,567
includes taxes & fees
24 Nov - 25 Nov
Cherry Tree Farm

3. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (3 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
Cherry Tree Cottage

4. 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 S$564
includes taxes & fees
4 Nov - 5 Nov
Little Mill

5. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
Carr House Farm

6. Overton

Overton
3.0 star property
Chesterfield
Overton

7. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is S$1,233
includes taxes & fees
6 Nov - 7 Nov
The Old Stables

8. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is S$812
includes taxes & fees
14 Nov - 15 Nov
Thorntree Lodge

9. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is S$669
includes taxes & fees
15 Nov - 16 Nov
Cedar Cottage

10. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
Riber View Barn

11. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
Harry's Lodge

12. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is S$1,063
includes taxes & fees
14 Nov - 15 Nov
The Cottage

13. The Tack Room Cottage

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

14. The Loft

The Loft
3.5 star property
Chesterfield
The price is S$1,025
includes taxes & fees
9 Nov - 10 Nov
The Loft
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

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.