Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Chesterfield vacation rentals

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

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is CA $508
CA $610 total
includes taxes & fees
Apr 26 - Apr 27
Cuckoo Nest
Fridge, microwave, oven, stovetop

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is CA $148
CA $194 total
includes taxes & fees
Mar 30 - Mar 31
a quiet semi rural property located in bolsover
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
The price is CA $137
CA $165 total
includes taxes & fees
Mar 30 - Mar 31
2bed - Garden-pets-freeparking-m1connections
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
The price is CA $186
CA $205 total
includes taxes & fees
Apr 21 - Apr 22
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.
The price is CA $266
CA $303 total
includes taxes & fees
Mar 29 - Mar 30
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Outdoor dining

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is CA $932
CA $932 total
includes taxes & fees
Mar 30 - Mar 31
Bryn Tor - The Gardener's House
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
The price is CA $526
CA $526 total
includes taxes & fees
Mar 27 - Mar 28
2 bedroom accommodation in Holymoorside
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.
The price is CA $170
CA $170 total
includes taxes & fees
Mar 31 - Apr 1
2bed - garden-pets-freeparking-M1connections
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
The price is CA $718
CA $718 total
includes taxes & fees
Mar 29 - Mar 30
Bathurst Cottage is a delightful three bedroom detached cottage.
Cottage | Exterior

The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"Out in the country but easy access to main routes. Nice and quiet. Very clean and well equipped. Nice owners. "
United Kingdom
Mark
The price is CA $694
CA $694 total
includes taxes & fees
Apr 26 - Apr 27
The Old Chapel
House | Private kitchen

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)
The price is CA $134
CA $184 total
includes taxes & fees
Apr 26 - Apr 27
2-bed House in Chesterfield Free Parking Garden
Cottage

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is CA $603
CA $723 total
includes taxes & fees
Apr 2 - Apr 3
Cedar Cottage
Fridge, microwave, oven, stovetop

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
Chesterfield
The price is CA $142
CA $189 total
includes taxes & fees
Mar 30 - Mar 31
a Quiet Semi Rural Property Located in Bolsover
Cottage | Property grounds

Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"The location is fine and the view beautiful. The owners were very helpful when needed. A most enjoyable stay."
Australia
Ian
The price is CA $567
CA $567 total
includes taxes & fees
Apr 8 - Apr 9
Shire Cottage at Top Butterley Farm
Terrace/patio

Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Everything was fantastic, fell in love witj the cottage , peaceful , perfect, I will come back again . Love it "
United Kingdom
toyin
The price is CA $994
CA $1,193 total
includes taxes & fees
Apr 26 - Apr 27
Cherry Tree Cottage
House | Exterior

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
Chesterfield
The price is CA $217
CA $305 total
includes taxes & fees
Mar 29 - Mar 30
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Cottage | Property grounds

Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is CA $682
CA $819 total
includes taxes & fees
Apr 10 - Apr 11
Harry's Lodge
Cottage | Outdoor dining

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is CA $952
CA $1,143 total
includes taxes & fees
Apr 26 - Apr 27
Moor Farm Cottage
Cottage | Living room

The Loft

The Loft
3.5 star property
Chesterfield
The price is CA $923
CA $1,108 total
includes taxes & fees
Mar 31 - Apr 1
The Loft
Cottage | Private kitchen

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is CA $732
CA $878 total
includes taxes & fees
Apr 26 - Apr 27
Thorntree Lodge
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

Radisson Blu Hotel, Sheffield

Radisson Blu Hotel, Sheffield

10/10 Excellent
"Large standard room. Everything you need "
Lucy 2-night trip
Posted 3 hours ago
Radisson Blu Hotel, Sheffield

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.

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?

Perfect for all Large Groups in 7 all Ensuite Bedrooms . Pet Friendly: You might want to consider this vacation rental near Chesterfield, which offers a private balcony, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals will I find in Chesterfield?

With 37 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 Pomegranate Theatre. 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.