Chesterfield Vacation Rentals from $79: Search Short-Term Rentals

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Our top choices for Chesterfield vacation rentals

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

1. Commuters Getaway Chesterfield

Chesterfield

$129 nightly

Sep 6 - Sep 7

Total with taxes and fees

2. 2 bedroom accommodation in Holymoorside

Holymoorside

V & P Roberts

$461 nightly

Aug 9 - Aug 10

Total with taxes and fees

3. Cherry Tree Cottage

Chesterfield

Lorraine

$732 nightly

Aug 16 - Aug 17

Total with taxes and fees

4. 2bed - garden-pets-freeparking-M1connections

Chesterfield

Ray W.

$149 nightly

Aug 17 - Aug 18

Total with taxes and fees

5. a quiet semi rural property located in bolsover

Chesterfield

$169 nightly

Aug 12 - Aug 13

Total with taxes and fees

6. Riber View Barn, Ashover

Chesterfield

$465 nightly

Aug 16 - Aug 17

Total with taxes and fees

7. The Old Stables, Ashover

Chesterfield

Duncan M.

$1,059 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Bryn Tor - The Gardener's House

Bolsover, near Chesterfield

$744 nightly

Aug 10 - Aug 11

Total with taxes and fees

9. 2bed - Garden-pets-freeparking-m1connections

Chesterfield

Philip

$123 nightly

Aug 12 - Aug 13

Total with taxes and fees

10. Overton

Chesterfield

$645 nightly

Aug 13 - Aug 14

Total with taxes and fees

11. a Quiet Semi Rural Property Located in Bolsover

Chesterfield

$170 nightly

Aug 9 - Aug 10

Total with taxes and fees

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

12. Cedar Cottage

Chesterfield

$444 nightly

Aug 15 - Aug 16

Total with taxes and fees

13. Wigley Farm House Cottage

Chesterfield

$694 nightly

Aug 15 - Aug 16

Total with taxes and fees

Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

14. Thorntree Lodge

Chesterfield

$539 nightly

Aug 12 - Aug 13

Total with taxes and fees

15. Riber View Barn

Chesterfield

$377 nightly

Aug 16 - Aug 17

Total with taxes and fees

16. Harry's Lodge

Chesterfield

$578 nightly

Aug 13 - Aug 14

Total with taxes and fees

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

17. Cuckoo Nest

Chesterfield

$374 nightly

Aug 11 - Aug 12

Total with taxes and fees

18. Woodthorpe Cruck Cottage

Chesterfield

Anthony

$701 nightly

Aug 31 - Sep 1

Total with taxes and fees

19. The Cottage

Chesterfield

$706 nightly

Aug 21 - Aug 22

Total with taxes and fees

20. Shire Cottage at Top Butterley Farm

Chesterfield

Ian

$456 nightly

Aug 21 - Aug 22

Total with taxes and fees

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Top Chesterfield Hotel Reviews

Leonardo Hotel Nottingham

10/10 Excellent

"Clean tidy room very helpful staff"

Hex Wildlife Hotel

8/10 Good

"We had a great stay overall. We were pleasantly surprised to be upgraded from a twin room to a family room, which gave us plenty of extra space and was much appreciated. Check-in was quick and easy, and the staff were friendly and efficient. The room was modern, tidy, and comfortable, with everything we needed for our stay. The only small criticism is that the room could have been a little cleaner, as there were a few cobwebs around the windows. It wasn't a major issue and didn't affect our stay, but it's something that could easily be improved. Overall, we had a positive experience and would happily stay here again."

The Orchard Hotel & Restaurant

10/10 Excellent

"We have taken weekend breaks as a couple at the Orchard for a number of years. We do bed and breakfast. We have always loved the location and the hotel. The recent refurbishment of the foyer, bar and dining room have transformed the space creating a spacious but intimate environment. The breakfast at Bramleys is excellent and good value. In the past we would sometimes have taken breakfast elsewhere, no longer. The staff we all helpful and welcoming."

WILDES INNS

8/10 Good

"attended a wedding here so decided to stay over,the hotel room was lovely and clean,bed was very uncomfortable,shower was great.the breakfast was great with excellent selection of food. The only fault we had was that the bedroom window wouldn’t close,which didn’t seem a problem when we returned back to our room later in the night,but from 5am all we could hear noise of the traffic,so had about 4hours sleep all night,so if you are booking i recommend asking for a room not facing the road"

Buxton Crescent

8/10 Good

"The hotel is ideally located to enjoy the best of Buxton. It is beautifully decorated, with a real sense of luxury. Our room was spotless and the bed very comfy. Staff were helpful and polite. My only disappointment was the breakfast service and in all truth this was completely unacceptable. It was apparent that the kitchen and service was heavily understaffed, which impacted upon the cleanliness, insufficient stocks on the buffet service and delays serving food. Most people had a 45min delay for hot breakfast, and this resulted in us and a number of other guests requesting refunds. The serving staff were very apologetic and just looked worn out and embarrassed."

Sandman Signature Sheffield Quays Hotel

8/10 Good

"I think the value for money was excellent. The rooms were modern, clean and comfortable. The only complaint with the room was the lighting being too dark, albeit a very modern lighting setup. However, I have to state as someone allergic to Gluten, the hotel and restaurant have absolutely ZERO ability to deal with this and therefore neither dinner nor breakfast was an option."

voco Sheffield by IHG

8/10 Good

"Great hotel but it clearly needs a refurb now. The rooms are nice but the decor a bit old fashioned and showing signs of a lot of wear and tear. The corridors and panelling are chipped and bashed and the pool area and sauna etc missing tiles. It’s in a great location and the rooms and bathrooms are a great size and the mattress really comfy. Staff are really helpful and the onsite bar and restaurant are really nice. As I say, just needs a refurb to bring it up to speed."

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.

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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?

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .: Visitors like this Chesterfield vacation home rental. It 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 45 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.

Chesterfield Vacation Rentals

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Check prices for these dates

Our top choices for Chesterfield vacation rentals

1. Commuters Getaway Chesterfield

2. 2 bedroom accommodation in Holymoorside

3. Cherry Tree Cottage

4. 2bed - garden-pets-freeparking-M1connections

5. a quiet semi rural property located in bolsover

6. Riber View Barn, Ashover

7. The Old Stables, Ashover

8. Bryn Tor - The Gardener's House

9. 2bed - Garden-pets-freeparking-m1connections

10. Overton

11. a Quiet Semi Rural Property Located in Bolsover

12. Cedar Cottage

13. Wigley Farm House Cottage

14. Thorntree Lodge

15. Riber View Barn

16. Harry's Lodge

17. Cuckoo Nest

18. Woodthorpe Cruck Cottage

19. The Cottage

20. Shire Cottage at Top Butterley Farm

Find vacation rentals that suit your style

Top Chesterfield Hotel Reviews

Leonardo Hotel Nottingham

Find out more about Chesterfield

Explore a world of travel with Expedia

Frequently asked questions

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