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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterfield holiday rentals

A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

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
The price is ฿3,421
฿5,194 total
includes taxes & fees
22 Nov - 23 Nov
2bed - Garden-pets-freeparking-m1connections
A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

2. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
The price is ฿18,456
฿22,147 total
includes taxes & fees
17 Nov - 18 Nov
Carr House Farm
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

3. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is ฿56,693
฿68,031 total
includes taxes & fees
24 Nov - 25 Nov
Cherry Tree Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

4. 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
The price is ฿24,673
฿29,607 total
includes taxes & fees
22 Nov - 23 Nov
Cherry Tree Cottage
A stone building with a water wheel and a staircase.

5. 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 ฿12,458
฿14,950 total
includes taxes & fees
14 Nov - 15 Nov
Little Mill
A cozy cabin-style interior with a kitchen, dining area, and seating space.

6. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is ฿19,908
฿23,889 total
includes taxes & fees
12 Nov - 13 Nov
Thorntree Lodge
A sunlit room with a large window, a sofa, a table, and a potted plant.

7. Overton

Overton
3.0 star property
Chesterfield
The price is ฿23,832
฿28,598 total
includes taxes & fees
16 Nov - 17 Nov
Overton
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

8. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is ฿30,221
฿36,265 total
includes taxes & fees
19 Nov - 20 Nov
The Old Stables
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

9. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is ฿16,424
฿19,709 total
includes taxes & fees
8 Nov - 9 Nov
Cedar Cottage
A stone building with a wooden door, a hose, and a horse in the background.

10. The Loft

The Loft
3.5 star property
Chesterfield
The price is ฿25,106
฿30,128 total
includes taxes & fees
12 Nov - 13 Nov
The Loft
A wooden deck with outdoor seating and a glass door leading to a covered area.

11. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is ฿21,377
฿25,652 total
includes taxes & fees
20 Nov - 21 Nov
Harry's Lodge
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

12. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is ฿25,360
฿30,432 total
includes taxes & fees
9 Nov - 10 Nov
Swallows Barn
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

13. 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 ฿23,593
฿28,312 total
includes taxes & fees
3 Dec - 4 Dec
Woodthorpe Cruck Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

14. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is ฿23,458
฿28,150 total
includes taxes & fees
12 Nov - 13 Nov
The Tack Room Cottage
A rural road with stone walls and a stone building with a sign.

15. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is ฿14,181
฿17,017 total
includes taxes & fees
20 Nov - 21 Nov
Riber View 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

mour Hotel

mour Hotel

8/10 Good
"Like the hotel and stayed a number of times but found the bed to be uncomfortable this time. Enjoyed dinner and service was good."
Alan 1-night trip
Posted 15 hours ago
mour Hotel

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! 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 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.