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

A brick building with a wooden fence, a paved path, and a bicycle.

1. The Old School House

The Old School House
Brimington
The price is CA $289
CA $315 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is CA $142
CA $216 total
includes taxes & fees
Nov 22 - Nov 23
2bed - Garden-pets-freeparking-m1connections
A stone building with a water wheel and a staircase.

3. 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 CA $576
CA $691 total
includes taxes & fees
Nov 14 - Nov 15
Little Mill
A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

4. a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is CA $200
CA $248 total
includes taxes & fees
Nov 8 - Nov 9
a quiet semi rural property located in bolsover
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.
The price is CA $190
CA $228 total
includes taxes & fees
Nov 22 - Nov 23
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
The price is CA $504
CA $504 total
includes taxes & fees
Nov 12 - Nov 13
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
The price is CA $1,044
CA $1,044 total
includes taxes & fees
Nov 9 - Nov 10
Bryn Tor - The Gardener's House
A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

8. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is CA $201
CA $248 total
includes taxes & fees
Nov 8 - Nov 9
a Quiet Semi Rural Property Located in Bolsover
A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

9. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
The price is CA $767
CA $921 total
includes taxes & fees
Nov 19 - Nov 20
Carr House Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

10. 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 CA $1,026
CA $1,231 total
includes taxes & fees
Nov 22 - Nov 23
Cherry Tree Cottage
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

11. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is CA $2,358
CA $2,829 total
includes taxes & fees
Dec 2 - Dec 3
Cherry Tree Farm
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 CA $829
CA $995 total
includes taxes & fees
Nov 20 - Nov 21
Thorntree Lodge
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

13. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is CA $683
CA $820 total
includes taxes & fees
Nov 16 - Nov 17
Cedar Cottage
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

14. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is CA $1,259
CA $1,510 total
includes taxes & fees
Nov 16 - Nov 17
The Old Stables
A sunlit room with a large window, a sofa, a table, and a potted plant.

15. Overton

Overton
3.0 star property
Chesterfield
The price is CA $991
CA $1,189 total
includes taxes & fees
Nov 19 - Nov 20
Overton
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
The price is CA $889
CA $1,067 total
includes taxes & fees
Nov 20 - Nov 21
Harry's Lodge
A stone building with a pitched roof, a small porch, and a stone wall in the background.

17. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is CA $590
CA $708 total
includes taxes & fees
Nov 23 - Nov 24
Riber View Barn
A living room with a stone wall, a fireplace, leather sofas, and a television.

18. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is CA $968
CA $1,162 total
includes taxes & fees
Dec 6 - Dec 7
The Cottage
A rustic interior with exposed wooden beams, a stone wall, and a leather sofa.

19. The Loft

The Loft
3.5 star property
Chesterfield
The price is CA $1,046
CA $1,255 total
includes taxes & fees
Nov 11 - Nov 12
The Loft
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

20. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is CA $1,056
CA $1,267 total
includes taxes & fees
Nov 16 - Nov 17
Swallows 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

Sandman Signature Sheffield Quays Hotel

Sandman Signature Sheffield Quays Hotel

10/10 Excellent
"Very clean and quiet room. Staff very welcoming. Pool excellent. Add £10 for parking for 24 hours. Bring a hairdryer if you need one."
Joan 1-night trip
Posted less than an hour ago
Sandman Signature Sheffield Quays 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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard 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.