The tow path on the Chesterfield canal on a bright sunny day

Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $141
CA $214 total
includes taxes & fees
Sep 1 - Sep 2
Commuters Getaway Chesterfield

2. 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.
The price is CA $171
CA $209 total
includes taxes & fees
Aug 17 - Aug 18
2bed - garden-pets-freeparking-M1connections

3. a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is CA $190
CA $237 total
includes taxes & fees
Aug 16 - Aug 17
a quiet semi rural property located in bolsover

4. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is CA $2,700
CA $3,240 total
includes taxes & fees
Sep 8 - Sep 9
Cherry Tree Farm

5. 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
The price is CA $596
CA $596 total
includes taxes & fees
Sep 9 - Sep 10
2 bedroom accommodation in Holymoorside

6. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is CA $1,041
CA $1,041 total
includes taxes & fees
Aug 31 - Sep 1
Bryn Tor - The Gardener's House

7. 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
The price is CA $141
CA $214 total
includes taxes & fees
Aug 17 - Aug 18
2bed - Garden-pets-freeparking-m1connections

8. Overton

Overton
2.0 star property
Chesterfield
The price is CA $900
CA $1,080 total
includes taxes & fees
Aug 18 - Aug 19
Overton

9. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is CA $190
CA $237 total
includes taxes & fees
Aug 16 - Aug 17
a Quiet Semi Rural Property Located in Bolsover

10. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is CA $1,024
CA $1,228 total
includes taxes & fees
Sep 2 - Sep 3
Cherry Tree Cottage

11. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is CA $1,288
CA $1,546 total
includes taxes & fees
Sep 1 - Sep 2
Swallows Barn

12. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is CA $548
CA $658 total
includes taxes & fees
Aug 25 - Aug 26
Riber View Barn

13. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
Harry's Lodge

14. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is CA $969
CA $1,162 total
includes taxes & fees
Sep 4 - Sep 5
Wigley Farm House Cottage

15. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is CA $523
CA $627 total
includes taxes & fees
Aug 17 - Aug 18
Cuckoo Nest

16. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is CA $620
CA $744 total
includes taxes & fees
Aug 18 - Aug 19
Cedar Cottage

17. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is CA $753
CA $904 total
includes taxes & fees
Aug 21 - Aug 22
Thorntree Lodge

18. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is CA $980
CA $1,176 total
includes taxes & fees
Sep 4 - Sep 5
Moor Farm Cottage

19. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is CA $882
CA $1,059 total
includes taxes & fees
Aug 16 - Aug 17
The Loft at The George

20. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is CA $1,143
CA $1,372 total
includes taxes & fees
Aug 31 - Sep 1
The Old Stables
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 46 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. Bolsover Castle and Hardwick Hall 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.