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

Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesterfield holiday rentals

Property grounds

1. The Old School House

The Old School House
Brimington
The price is AU$336
includes taxes & fees
31 Oct - 1 Nov
The Old School House
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is AU$3,123
includes taxes & fees
15 Nov - 16 Nov
Cherry Tree Farm
A wooden deck with two wicker sofas and a table, surrounded by a white lattice fence.

3. 2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (5 reviews)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
The price is AU$531
includes taxes & fees
31 Oct - 1 Nov
2 bedroom accommodation in Holymoorside
A dining area with a wooden table and chairs, a stone wall, and a view of the garden through a glass door.

4. Bathurst Cottage is a delightful three bedroom detached cottage.

Bathurst Cottage is a delightful three bedroom detached cottage.
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"Spotless, well looked after cottage. Very homely and cosy.Well equipped kitchen.Lovely hosts, great welcome hamper with lovely treats."
United States
Valerie Thompson
The price is AU$512
includes taxes & fees
16 Nov - 17 Nov
Bathurst Cottage is a delightful three bedroom detached cottage.
A cozy living room with a fireplace, comfortable seating, and a large window with curtains.

5. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is AU$1,061
includes taxes & fees
21 Oct - 22 Oct
Bryn Tor - The Gardener's House
A natural landscape with a stream, trees, and a grassy area.

6. 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 AU$640
includes taxes & fees
23 Oct - 24 Oct
Little Mill
A living room with a brown leather sofa, a wooden cabinet, a television, and a radiator.

7. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is AU$853
includes taxes & fees
17 Nov - 18 Nov
Carr House Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

8. 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 AU$1,252
includes taxes & fees
24 Oct - 25 Oct
Cherry Tree Cottage
A sunlit room with a large window, a sofa, a table, and a potted plant.

9. Overton

Overton
2.0 star property
Chesterfield
Overton
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

10. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is AU$759
includes taxes & fees
20 Oct - 21 Oct
Cedar Cottage
A stone building with a pitched roof, a small porch, and a stone wall in the background.

11. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is AU$671
includes taxes & fees
2 Nov - 3 Nov
Riber View Barn
A cozy cabin-style interior with a kitchen, dining area, and seating space.

12. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is AU$922
includes taxes & fees
31 Oct - 1 Nov
Thorntree Lodge
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

13. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is AU$1,399
includes taxes & fees
20 Oct - 21 Oct
The Old Stables
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.

14. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is AU$640
includes taxes & fees
30 Oct - 31 Oct
Cuckoo Nest
A wooden deck with outdoor seating and a glass door leading to a covered area.

15. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is AU$988
includes taxes & fees
17 Nov - 18 Nov
Harry's Lodge
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

16. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
A living room with a stone wall, a fireplace, leather sofas, and a television.

17. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is AU$1,205
includes taxes & fees
26 Oct - 27 Oct
The Cottage
A hot tub in a backyard with a stone wall and a grassy lawn.

18. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
6.0 out of 10, (1 review)
"I'll start with the good. Location is nice and peaceful. The bungalow is well laid out and there is plenty of room. Facilities inside the bungalow are good. Cooking and dining implements all there and lots of space. Bedrooms are nice and have plenty of storage for a short break. The garden is well maintained and enclosed although there is only 2 comfortable chairs and no swing or sofa. Parking around the back of the property is the best but you are encouraged to park at the front tucked...
United Kingdom
June
The price is AU$1,185
includes taxes & fees
26 Oct - 27 Oct
Wigley Farm House Cottage
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

19. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is AU$1,199
includes taxes & fees
15 Nov - 16 Nov
Moor Farm Cottage
A stone building with a sign reading "The George Country Pub & Dining."

20. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is AU$1,080
includes taxes & fees
5 Nov - 6 Nov
The Loft at The George
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

The Welcome Inn Hotel

The Welcome Inn Hotel

8/10 Good
"Free parking on site. Room was clean and roomy. Tea and coffee making facilities. Clean bathroom. Great value for money. Would definitely stay again."
Becci 1-night trip
Posted 3 hours ago
The Welcome Inn Hotel

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$118 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.