Chesterfield Vacation Rentals from $75: Search Short-Term Rentals

Q: 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.

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Our top choices for Chesterfield vacation rentals

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

1. Commuters Getaway Chesterfield

Chesterfield

$117 nightly

Sep 25 - Sep 26

Total with taxes and fees

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

Chesterfield

Ray W.

$148 nightly

Sep 23 - Sep 24

Total with taxes and fees

3. a quiet semi rural property located in bolsover

Chesterfield

$169 nightly

Sep 26 - Sep 27

Total with taxes and fees

4. Little Mill

Chesterfield

$372 nightly

Sep 23 - Sep 24

Total with taxes and fees

5. 2 bedroom accommodation in Holymoorside

Holymoorside

V & P Roberts

$370 nightly

Sep 25 - Sep 26

Total with taxes and fees

6. Bryn Tor - The Gardener's House

Bolsover, near Chesterfield

$739 nightly

Sep 25 - Sep 26

Total with taxes and fees

7. 2bed - Garden-pets-freeparking-m1connections

Chesterfield

Philip

$117 nightly

Sep 25 - Sep 26

Total with taxes and fees

8. Cherry Tree Farm

Chesterfield

$1,804 nightly

Sep 23 - Sep 24

Total with taxes and fees

9. a Quiet Semi Rural Property Located in Bolsover

Chesterfield

$169 nightly

Sep 27 - Sep 28

Total with taxes and fees

10. Carr House Farm

Chesterfield

$495 nightly

Oct 4 - Oct 5

Total with taxes and fees

11. Overton

Chesterfield

$639 nightly

Oct 5 - Oct 6

Total with taxes and fees

12. Cherry Tree Cottage

Chesterfield

Lorraine

$729 nightly

Sep 29 - Sep 30

Total with taxes and fees

13. Swallows Barn

Chesterfield

$880 nightly

Oct 6 - Oct 7

Total with taxes and fees

Cottage | 3 bedrooms, WiFi (free), individually decorated, individually furnished

14. Cedar Cottage

Chesterfield

$441 nightly

Oct 5 - Oct 6

Total with taxes and fees

15. The Old Chapel

Chesterfield

Mark

$507 nightly

Oct 17 - Oct 18

Total with taxes and fees

16. The Loft at The George

Chesterfield

$627 nightly

Sep 23 - Sep 24

Total with taxes and fees

17. Wigley Farm House Cottage

Chesterfield

"I'll start with the good. Location is nice and peaceful. The bungalow is well laid out and there is plenty of room. Facilities inside the bungalow are good. Cooking and dining implements all there and lots of space. Bedrooms are nice and have plenty of storage for a short break. The garden is well maintained and enclosed although there is only 2 comfortable chairs and no swing or sofa. Parking around the back of the property is the best but you are encouraged to park at the front tucked...

June

$690 nightly

Sep 28 - Sep 29

Total with taxes and fees

Cottage | 4 bedrooms, WiFi (free), individually decorated, individually furnished

18. The Old Stables

Chesterfield

$814 nightly

Sep 23 - Sep 24

Total with taxes and fees

19. Moor Farm Cottage

Chesterfield

$696 nightly

Oct 9 - Oct 10

Total with taxes and fees

Fridge, dishwasher, electric kettle, cookware/dishes/utensils

20. Cuckoo Nest

Chesterfield

$372 nightly

Sep 26 - Sep 27

Total with taxes and fees

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Top Chesterfield Hotel Reviews

B&B HOTEL Derby

8/10 Good

"Good value, nice and modern"

Leonardo Hotel Nottingham

10/10 Excellent

"I booked this hotel due to a show at motorpoint Arena Nottingham for location,knowing there is no parking tho not an issue as we used the train station so only a few minutes walk away,no problem for us.Friendly & quick check-in we were on 3rd floor but I did ask for high floor but not an issue,the room was very clean & comfortable,we had breakfast included in our price which was excellent,I simply couldn't fault this hotel & we will be returning in the future,we also ate in the restaurant which was lovely too,all the staff we met were lovely,see you again soon"

The Jubilee Hotel & Conferences

10/10 Excellent

"Great location, I’ve stayed here many times over the past few years. Hotel offers free car parking. And great views of Jubilee Campus. The Flexi card (to access the room using my phone) didn’t work. So I had to get a physical card. But other than that - a straightforward visit. Sometimes noise from the atrium did echo around the building - but it wasn’t a huge problem"

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 $75 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.

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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 44 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.

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Check prices for these dates

Our top choices for Chesterfield vacation rentals

1. Commuters Getaway Chesterfield

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

3. a quiet semi rural property located in bolsover

4. Little Mill

5. 2 bedroom accommodation in Holymoorside

6. Bryn Tor - The Gardener's House

7. 2bed - Garden-pets-freeparking-m1connections

8. Cherry Tree Farm

9. a Quiet Semi Rural Property Located in Bolsover

10. Carr House Farm

11. Overton

12. Cherry Tree Cottage

13. Swallows Barn

14. Cedar Cottage

15. The Old Chapel

16. The Loft at The George

17. Wigley Farm House Cottage

18. The Old Stables

19. Moor Farm Cottage

20. Cuckoo Nest

Find vacation rentals that suit your style

Top Chesterfield Hotel Reviews

B&B HOTEL Derby

Leonardo Hotel Nottingham

Leonardo Hotel Sheffield

Radisson Blu Hotel, Sheffield

ibis Budget Sheffield Centre St Marys Gate

Twin Oaks Hotel

The Jubilee Hotel & Conferences

Find out more about Chesterfield

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