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

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chesterfield holiday rentals

A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

1. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is RM7,819
RM9,383 total
includes taxes & fees
13 Oct - 14 Oct
Cherry Tree Farm
A natural landscape with a stream, trees, and a grassy area.

2. Little Mill

Little Mill
2.0 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 RM1,502
RM1,802 total
includes taxes & fees
12 Oct - 13 Oct
Little Mill
A living room with a brown leather sofa, a wooden cabinet, a television, and a radiator.

3. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is RM2,002
RM2,402 total
includes taxes & fees
15 Oct - 16 Oct
Carr House Farm
A cozy cabin-style interior with a kitchen, dining area, and seating space.

4. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is RM2,163
RM2,595 total
includes taxes & fees
14 Oct - 15 Oct
Thorntree Lodge
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

5. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is RM1,782
RM2,138 total
includes taxes & fees
18 Oct - 19 Oct
Cedar Cottage
A hot tub under a wooden pergola with a stone wall and greenery in the background.

6. 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 RM2,939
RM3,526 total
includes taxes & fees
15 Oct - 16 Oct
Cherry Tree Cottage
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

7. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is RM3,283
RM3,940 total
includes taxes & fees
12 Oct - 13 Oct
The Old Stables
A sunlit room with a large window, a sofa, a table, and a potted plant.

8. Overton

Overton
2.0 star property
Chesterfield
The price is RM2,585
RM3,102 total
includes taxes & fees
1 Nov - 2 Nov
Overton
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

9. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is RM2,755
RM3,306 total
includes taxes & fees
6 Nov - 7 Nov
Swallows Barn
A wooden deck with outdoor seating and a glass door leading to a covered area.

10. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is RM2,319
RM2,783 total
includes taxes & fees
22 Oct - 23 Oct
Harry's Lodge
A rustic interior with exposed wooden beams, a stone wall, and a leather sofa.

11. The Loft

The Loft
3.5 star property
Chesterfield
The price is RM2,728
RM3,273 total
includes taxes & fees
12 Oct - 13 Oct
The Loft
A modern kitchen with white cabinets, a wooden countertop, and a built-in sink. There is a wooden ladder leaning against the wall and a sliding glass door leading to an outdoor deck.

12. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is RM1,502
RM1,802 total
includes taxes & fees
14 Oct - 15 Oct
Cuckoo Nest
A stone building with a pitched roof, a small porch, and a stone wall in the background.

13. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is RM1,575
RM1,890 total
includes taxes & fees
16 Oct - 17 Oct
Riber View Barn
A living room with a stone wall, a fireplace, leather sofas, and a television.

14. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is RM2,829
RM3,394 total
includes taxes & fees
2 Nov - 3 Nov
The Cottage
A stone building with a sign reading "The George Country Pub & Dining."

15. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is RM2,535
RM3,042 total
includes taxes & fees
12 Oct - 13 Oct
The Loft at The George
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

16. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is RM2,548
RM3,058 total
includes taxes & fees
31 Oct - 1 Nov
The Tack Room Cottage
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

Four Points Flex by Sheraton Nottingham

Four Points Flex by Sheraton Nottingham

10/10 Excellent
"Fresh clean room, attentive service and a handy well priced carpark. Great site for a trip to the theatre. Loved our stay and will do so again."
steve 1-night trip
Posted 9 hours ago
Four Points Flex by Sheraton Nottingham

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.