Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

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 $690
CA $690 total
includes taxes & fees
Feb 27 - Feb 28
The Old Chapel

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 review)
The price is CA $153
CA $206 total
includes taxes & fees
Mar 5 - Mar 6
2-bed House in Chesterfield Free Parking Garden

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 $574
CA $574 total
includes taxes & fees
Feb 26 - Feb 27
Bathurst Cottage is a delightful three bedroom detached cottage.

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 $533
CA $533 total
includes taxes & fees
Feb 8 - Feb 9
2 bedroom accommodation in Holymoorside

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 $267
CA $304 total
includes taxes & fees
Feb 8 - Feb 9
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

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 $197
CA $197 total
includes taxes & fees
Feb 11 - Feb 12
2bed - garden-pets-freeparking-M1connections

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is CA $197
CA $243 total
includes taxes & fees
Feb 13 - Feb 14
a quiet semi rural property located in bolsover

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 $564
CA $564 total
includes taxes & fees
Feb 13 - Feb 14
Shire Cottage at Top Butterley Farm

2br-towncentre-garden-freeparking-pets

2br-towncentre-garden-freeparking-pets
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 $195
CA $214 total
includes taxes & fees
Feb 8 - Feb 9
2br-towncentre-garden-freeparking-pets

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 $220
CA $309 total
includes taxes & fees
Feb 10 - Feb 11
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is CA $505
CA $606 total
includes taxes & fees
Feb 10 - Feb 11
Cuckoo Nest

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 $192
CA $239 total
includes taxes & fees
Feb 23 - Feb 24
a Quiet Semi Rural Property Located in Bolsover

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 $163
CA $196 total
includes taxes & fees
Feb 11 - Feb 12
2bed - Garden-pets-freeparking-m1connections

The Old Grocery

The Old Grocery
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is CA $721
CA $721 total
includes taxes & fees
Feb 15 - Feb 16
The Old Grocery

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is CA $728
CA $873 total
includes taxes & fees
Feb 13 - Feb 14
Thorntree Lodge

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is CA $599
CA $719 total
includes taxes & fees
Feb 10 - Feb 11
Cedar Cottage

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 $989
CA $1,187 total
includes taxes & fees
Feb 10 - Feb 11
Cherry Tree Cottage

Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage
3.5 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is CA $946
CA $1,135 total
includes taxes & fees
Feb 22 - Feb 23
Woodthorpe Cruck Cottage

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is CA $947
CA $1,136 total
includes taxes & fees
Feb 10 - Feb 11
Moor Farm Cottage

The Loft

The Loft
3.5 star property
Chesterfield
The price is CA $918
CA $1,101 total
includes taxes & fees
Feb 10 - Feb 11
The Loft
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.

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 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?

Rent My Spa Home with Pool table, Hottub and Sauna: This Chesterfield vacation home rental is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chesterfield?

With 38 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.