A historic building with black and white timber framing, a prominent clock tower, and a pointed spire in the background.

Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

2-bed House, Sleeps 4 w/ Parking & Garden

2-bed House, Sleeps 4 w/ Parking & Garden
2.0 star property
Chesterfield
$122 nightly
The price is $146
Jun 24 - Jun 25
Total with taxes and fees
2-bed House, Sleeps 4 w/ Parking & Garden

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
$166 nightly
The price is $166
Jul 3 - Jul 4
Total with taxes and fees
a quiet semi rural property located in bolsover

2-Bed House, Sleeps 4 w/ Parking & Garden

2-Bed House, Sleeps 4 w/ Parking & Garden
Chesterfield
$158 nightly
The price is $158
Jul 2 - Jul 3
Total with taxes and fees
2-Bed House, Sleeps 4 w/ Parking & Garden

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
$368 nightly
The price is $441
Jun 26 - Jun 27
Total with taxes and fees
Cuckoo Nest

The Old Chapel, Handley

The Old Chapel, Handley
Chesterfield
$517 nightly
The price is $517
Jul 4 - Jul 5
Total with taxes and fees
The Old Chapel, Handley

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
$852 nightly
The price is $852
Jun 29 - Jun 30
Total with taxes and fees
Moor Farm Cottage near Ashover

The Old Stables, Ashover

The Old Stables, Ashover
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"This was a perfect place for our family get together. Very clean, well appointed, and lovely location. The owner was also extremely helpful when one of our party had an accident and escorted us tothe nearest urfent care centre. Highly recommended."
United Kingdom
Duncan M.
$993 nightly
The price is $993
Jun 29 - Jun 30
Total with taxes and fees
The Old Stables, Ashover

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.
$147 nightly
The price is $147
Jun 26 - Jun 27
Total with taxes and fees
2bed - garden-pets-freeparking-M1connections

Charming Tuliptree in Ashover

Charming Tuliptree in Ashover
Chesterfield
$682 nightly
The price is $682
Jul 3 - Jul 4
Total with taxes and fees
Charming Tuliptree in Ashover

The Rumblings 3, Barlow

The Rumblings 3, Barlow
Dronfield
$499 nightly
The price is $499
Jul 3 - Jul 4
Total with taxes and fees
The Rumblings 3, Barlow

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
$126 nightly
The price is $152
Jun 28 - Jun 29
Total with taxes and fees
Commuters Getaway Chesterfield

The Cottage, Chesterfield

The Cottage, Chesterfield
Chesterfield
$856 nightly
The price is $856
Jun 29 - Jun 30
Total with taxes and fees
The Cottage, Chesterfield

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
$496 nightly
The price is $496
Jun 25 - Jun 26
Total with taxes and fees
Bathurst Cottage is a delightful three bedroom detached cottage.

Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
$568 nightly
The price is $682
Jul 1 - Jul 2
Total with taxes and fees
Harry's Lodge

2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (4 reviews)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
$523 nightly
The price is $523
Jul 18 - Jul 19
Total with taxes and fees
2 bedroom accommodation in Holymoorside

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
$735 nightly
The price is $735
Jun 24 - Jun 25
Total with taxes and fees
Bryn Tor - The Gardener's House

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Pleasant, fresh suburban home in a quiet neighborhood. Worked well for us in a short stay. Thoughtfully decorated with new appliances and bath kit. "
United Kingdom
James F.
$217 nightly
The price is $217
Jul 3 - Jul 4
Total with taxes and fees
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

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
$119 nightly
The price is $143
Jun 26 - Jun 27
Total with taxes and fees
2bed - Garden-pets-freeparking-m1connections

Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
$519 nightly
The price is $622
Jun 26 - Jun 27
Total with taxes and fees
Wigley Farm House Cottage

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
$167 nightly
The price is $167
Jul 3 - Jul 4
Total with taxes and fees
a Quiet Semi Rural Property Located in Bolsover
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

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 $68 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?

2 Bed Derby House- Parking - Rolls Royce: Visitors like this Chesterfield vacation home rental. It offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Chesterfield?

With 48 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 Chesterfield Museum & Art Gallery. 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.