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

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
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

A kitchen with a black stove, white cabinets, a wooden cutting board, and potted plants on the windowsill.

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is RM416
RM631 total
includes taxes & fees
3 Sept - 4 Sept
Commuters Getaway Chesterfield
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

2. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is RM2,599
RM3,119 total
includes taxes & fees
4 Sept - 5 Sept
The Tack Room Cottage
A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

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 RM558
RM695 total
includes taxes & fees
31 Aug - 1 Sept
a Quiet Semi Rural Property Located in Bolsover
A rural landscape with a stone wall, a small building, and a view of the countryside.

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 RM1,866
RM1,866 total
includes taxes & fees
31 Aug - 1 Sept
Shire Cottage at Top Butterley Farm

5. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is RM1,532
RM1,838 total
includes taxes & fees
23 Sept - 24 Sept
Little Mill
A bedroom with a bed, a wardrobe, a window with curtains, and a door leading to another room.

6. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is RM2,042
RM2,451 total
includes taxes & fees
31 Aug - 1 Sept
Carr House Farm
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

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 RM2,811
RM3,373 total
includes taxes & fees
24 Sept - 25 Sept
Woodthorpe Cruck Cottage
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

8. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
Moor Farm Cottage
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 RM1,818
RM2,181 total
includes taxes & fees
29 Aug - 30 Aug
Cedar Cottage
A hot tub in a backyard with a stone wall and a grassy lawn.

10. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
Wigley Farm House Cottage
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

11. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is RM3,349
RM4,019 total
includes taxes & fees
31 Aug - 1 Sept
The Old Stables
A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

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 RM416
RM631 total
includes taxes & fees
1 Sept - 2 Sept
2bed - Garden-pets-freeparking-m1connections
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.

13. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is RM1,532
RM1,838 total
includes taxes & fees
7 Sept - 8 Sept
Cuckoo Nest
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 RM2,890
RM3,468 total
includes taxes & fees
11 Sept - 12 Sept
The Cottage
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

15. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
A rustic interior with exposed wooden beams, a stone wall, and a leather sofa.

16. The Loft

The Loft
3.5 star property
Chesterfield
The Loft
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

17. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is RM7,421
RM8,905 total
includes taxes & fees
23 Sept - 24 Sept
Cherry Tree Farm
A stone building with a sign reading "The George Country Pub & Dining."

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is RM2,585
RM3,103 total
includes taxes & fees
23 Sept - 24 Sept
The Loft at The George
A hot tub under a wooden pergola with a stone wall and greenery in the background.

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 RM2,998
RM3,597 total
includes taxes & fees
2 Sept - 3 Sept
Cherry Tree Cottage
A sunlit room with a large window, a sofa, a table, and a potted plant.

20. Overton

Overton
2.0 star property
Chesterfield
The price is RM2,637
RM3,164 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.
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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 11 hours ago
Leonardo Hotel Sheffield

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia.co.uk! 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
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  • 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.

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.