Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

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, (1)
$130 nightly
The price is $156
Dec 27 - Dec 28
Total with taxes and fees
2-bed House in Chesterfield Free Parking Garden

Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (2)
"The location is fine and the view beautiful. The owners were very helpful when needed. A most enjoyable stay."
Australia
Ian
$404 nightly
The price is $404
Dec 29 - Dec 30
Total with taxes and fees
Shire Cottage at Top Butterley Farm

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
$177 nightly
The price is $177
Jan 3 - Jan 4, 2026
Total with taxes and fees
a quiet semi rural property located in bolsover

2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
$143 nightly
The price is $143
Dec 22 - Dec 23
Total with taxes and fees
2bed - garden-pets-freeparking-M1connections

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Chesterfield
10.0 out of 10, Exceptional, (1)
"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.
$219 nightly
The price is $219
Dec 23 - Dec 24
Total with taxes and fees
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

2br-towncentre-garden-freeparking-pets

2br-towncentre-garden-freeparking-pets
Chesterfield
6.0 out of 10, (1)
"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
$157 nightly
The price is $157
Dec 27 - Dec 28
Total with taxes and fees
2br-towncentre-garden-freeparking-pets

2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (4)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
$383 nightly
The price is $383
Jan 4 - Jan 5, 2026
Total with taxes and fees
2 bedroom accommodation in Holymoorside

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)
"Spotless, well looked after cottage. Very homely and cosy.Well equipped kitchen.Lovely hosts, great welcome hamper with lovely treats."
United States
Valerie Thompson
$391 nightly
The price is $391
Jan 18 - Jan 19, 2026
Total with taxes and fees
Bathurst Cottage is a delightful three bedroom detached cottage.

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
2.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
"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 $142
Dec 22 - Dec 23
Total with taxes and fees
2bed - Garden-pets-freeparking-m1connections

Five Acres

Five Acres
3.0 star property
Chesterfield
$4,659 nightly
The price is $5,591
Jan 17 - Jan 18, 2026
Total with taxes and fees
Five Acres

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
Chesterfield
$184 nightly
The price is $221
Dec 25 - Dec 26
Total with taxes and fees
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
$430 nightly
The price is $516
Dec 27 - Dec 28
Total with taxes and fees
Cedar Cottage

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
Chesterfield
$173 nightly
The price is $173
Jan 2 - Jan 3, 2026
Total with taxes and fees
a Quiet Semi Rural Property Located in Bolsover

Riber View Barn

Riber View Barn
3.5 star property
Chesterfield
$433 nightly
The price is $433
Jan 7 - Jan 8, 2026
Total with taxes and fees
Riber View Barn

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
$521 nightly
The price is $625
Dec 28 - Dec 29
Total with taxes and fees
Thorntree Lodge

The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2)
"Out in the country but easy access to main routes. Nice and quiet. Very clean and well equipped. Nice owners. "
United Kingdom
Mark
$494 nightly
The price is $494
Dec 28 - Dec 29
Total with taxes and fees
The Old Chapel

The Loft

The Loft
3.5 star property
Chesterfield
$676 nightly
The price is $811
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Loft

Overton

Overton
2.0 star property
Chesterfield
$640 nightly
The price is $768
Jan 2 - Jan 3, 2026
Total with taxes and fees
Overton

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
$363 nightly
The price is $435
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cuckoo Nest

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
$679 nightly
The price is $815
Dec 29 - Dec 30
Total with taxes and fees
Moor Farm Cottage
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 $72 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.

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, you can find vacation rentals in Chesterfield close to The Herb Garden, or you can choose a secluded option if you want a relaxing stay. Our travelers say Chesterfield has a good selection of lively bars and top-notch restaurants. 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?

Studio Self contained flat free Parking: You might want to consider this vacation home rental near Chesterfield, which is near a train station and equipped with WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals will I find in Chesterfield?

With 36 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.