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

Our top choices for Chesterfield vacation rentals

Property grounds

1. The Old School House

The Old School House
Brimington
$224 nightly
The price is $224
Nov 8 - Nov 9
Total with taxes and fees
The Old School House
A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

2. 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
$128 nightly
The price is $154
Nov 22 - Nov 23
Total with taxes and fees
2bed - Garden-pets-freeparking-m1connections
A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

3. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
$491 nightly
The price is $589
Nov 30 - Dec 1
Total with taxes and fees
Carr House Farm
A wooden deck with two wicker sofas and a table, surrounded by a white lattice fence.

4. 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
2 bedroom accommodation in Holymoorside
A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

5. 2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3 reviews)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
$162 nightly
The price is $162
Nov 22 - Nov 23
Total with taxes and fees
2bed - garden-pets-freeparking-M1connections
A dining area with a wooden table and chairs, a stone wall, and a view of the garden through a glass door.

6. 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
$358 nightly
The price is $358
Nov 26 - Nov 27
Total with taxes and fees
Bathurst Cottage is a delightful three bedroom detached cottage.
A balcony with a view of a field, a table with chairs, and a potted plant.

7. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
$742 nightly
The price is $742
Nov 25 - Nov 26
Total with taxes and fees
Bryn Tor - The Gardener's House
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

8. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
$1,676 nightly
The price is $2,012
Nov 25 - Nov 26
Total with taxes and fees
Cherry Tree Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

9. 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
$657 nightly
The price is $788
Nov 25 - Nov 26
Total with taxes and fees
Cherry Tree Cottage
A welcome sign for Ashover Community First with a stone wall and flower box in the foreground.

10. 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
$368 nightly
The price is $442
Nov 23 - Nov 24
Total with taxes and fees
Little Mill
A cozy cabin-style interior with a kitchen, dining area, and seating space.

11. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
$531 nightly
The price is $637
Nov 23 - Nov 24
Total with taxes and fees
Thorntree Lodge
A sunlit room with a large window, a sofa, a table, and a potted plant.

12. Overton

Overton
3.0 star property
Chesterfield
$634 nightly
The price is $761
Nov 23 - Nov 24
Total with taxes and fees
Overton
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
$805 nightly
The price is $967
Nov 23 - Nov 24
Total with taxes and fees
The Old Stables
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

14. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
$437 nightly
The price is $524
Nov 23 - Nov 24
Total with taxes and fees
Cedar Cottage
A rustic interior with exposed wooden beams, a stone wall, and a leather sofa.

15. The Loft

The Loft
3.5 star property
Chesterfield
$669 nightly
The price is $803
Nov 23 - Nov 24
Total with taxes and fees
The Loft
A wooden deck with outdoor seating and a glass door leading to a covered area.

16. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
$569 nightly
The price is $683
Nov 28 - Nov 29
Total with taxes and fees
Harry's Lodge
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

17. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
$676 nightly
The price is $811
Nov 30 - Dec 1
Total with taxes and fees
Swallows Barn
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

18. 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
$628 nightly
The price is $753
Nov 12 - Nov 13
Total with taxes and fees
Woodthorpe Cruck Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

19. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
$625 nightly
The price is $750
Nov 30 - Dec 1
Total with taxes and fees
The Tack Room Cottage
A stone building with a pitched roof, a small porch, and a stone wall in the background.

20. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
$419 nightly
The price is $503
Nov 23 - Nov 24
Total with taxes and fees
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

Hex Wildlife Hotel

Hex Wildlife Hotel

10/10 Excellent
"This us our third time staying here. It’s always worth it. The only downside I’d say, is that, maybe they should open and independent convenience store outside. Thanks"
Rona Rose 1-night trip
Posted 13 hours ago
Hex Wildlife Hotel

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, you can find vacation rentals in Chesterfield close to Clay Cross Active, or you can choose a secluded option if you want a relaxing stay. Our travelers 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 vacation home rentals that Chesterfield has to offer?

Old Nags Head: You might want to consider this vacation home rental near Chesterfield, which comes with free WiFi so you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave, and kitchenware.

How many vacation rentals will I find in Chesterfield?

With 43 Expedia vacation rentals, you're sure 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 vacation rentals like in Chesterfield?

Vacation rentals are private properties you can stay in for several days or longer in Chesterfield. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.