Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chesterfield vacation rentals

House | Private kitchen | Fridge, microwave, oven, stovetop

2-bed House in Chesterfield Free Parking Garden

2-bed House in Chesterfield Free Parking Garden
2.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
$111 nightly
The price is $133
May 20 - May 21
Total with taxes and fees
2-bed House in Chesterfield Free Parking Garden
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
$376 nightly
The price is $451
May 18 - May 19
Total with taxes and fees
Cuckoo Nest
Fridge, microwave, oven, stovetop

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
Chesterfield
6.0 out of 10, (1 review)
"Needs blinds in both bathroom and kitchen also shower curtain. Non slip mat in bath would be helpful as would a printed information page ie parking and heating instructions. Guttering outside lounge needs checking as overflowing. Otherwise clean and nice place to stay."
United Kingdom
Pauline
$137 nightly
The price is $137
May 11 - May 12
Total with taxes and fees
Commuters Getaway Chesterfield
Exterior

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.
$222 nightly
The price is $222
May 7 - May 8
Total with taxes and fees
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
WiFi

Riber View Barn, Ashover

Riber View Barn, Ashover
Chesterfield
$459 nightly
The price is $459
May 25 - May 26
Total with taxes and fees
Riber View Barn, Ashover
Terrace/patio

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.
$123 nightly
The price is $123
May 11 - May 12
Total with taxes and fees
2bed - garden-pets-freeparking-M1connections
Living area

The Old Chapel, Handley

The Old Chapel, Handley
Chesterfield
$538 nightly
The price is $538
May 8 - May 9
Total with taxes and fees
The Old Chapel, Handley
WiFi

Cherry Fields, Bolsover

Cherry Fields, Bolsover
Chesterfield
$751 nightly
The price is $751
Jun 1 - Jun 2
Total with taxes and fees
Cherry Fields, Bolsover
Living area

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
$887 nightly
The price is $887
May 26 - May 27
Total with taxes and fees
Moor Farm Cottage near Ashover
Property grounds

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
$447 nightly
The price is $447
May 8 - May 9
Total with taxes and fees
2 bedroom accommodation in Holymoorside
Terrace/patio

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
2.0 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
$98 nightly
The price is $118
May 20 - May 21
Total with taxes and fees
2bed - Garden-pets-freeparking-m1connections
Property grounds

Little Mill

Little Mill
2.0 star property
Chesterfield
$376 nightly
The price is $451
May 22 - May 23
Total with taxes and fees
Little Mill
WiFi

The Rumblings 3, Barlow

The Rumblings 3, Barlow
Dronfield
$521 nightly
The price is $521
May 9 - May 10
Total with taxes and fees
The Rumblings 3, Barlow
Outdoor dining

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
$751 nightly
The price is $751
May 18 - May 19
Total with taxes and fees
Bryn Tor - The Gardener's House
Living area

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.
$1,035 nightly
The price is $1,035
May 29 - May 30
Total with taxes and fees
The Old Stables, Ashover
Dining

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
$470 nightly
The price is $470
May 8 - May 9
Total with taxes and fees
Bathurst Cottage is a delightful three bedroom detached cottage.
Living area

Charming Tuliptree in Ashover

Charming Tuliptree in Ashover
Chesterfield
$643 nightly
The price is $643
May 8 - May 9
Total with taxes and fees
Charming Tuliptree in Ashover
Fireplace

The Cottage, Chesterfield

The Cottage, Chesterfield
Chesterfield
$895 nightly
The price is $895
Jun 1 - Jun 2
Total with taxes and fees
The Cottage, Chesterfield
House | Exterior

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
Chesterfield
$186 nightly
The price is $223
May 18 - May 19
Total with taxes and fees
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Exterior

Riber View Barn

Riber View Barn
2.0 star property
Chesterfield
$365 nightly
The price is $437
May 25 - May 26
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

Derby Mickleover Hotel, BW Signature Collection

Derby Mickleover Hotel, BW Signature Collection

8/10 Good
"Clean helpful.staff and restaurant food was quick.and delicious "
Char 1-night trip
Posted 2 hours ago
Derby Mickleover Hotel, BW Signature Collection

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?

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .: You might want to consider this vacation home rental near Chesterfield, which offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven.

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 Chesterfield Museum & Art Gallery and Barrow Hill Roundhouse Railway Centre. 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.