Chesterfield Vacation Rentals

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chesterfield vacation rentals

House | Private kitchen | Fridge, microwave, oven, stovetop
2-bed House in Chesterfield Free Parking Garden

Residence in Chesterfield

2-bed House in Chesterfield Free Parking Garden
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ₩175,445
₩234,256 total
includes taxes & fees
Dec 29 - Dec 30
2-bed House in Chesterfield Free Parking Garden
Cottage | Property grounds
Shire Cottage at Top Butterley Farm

Cottage in Chesterfield

Shire Cottage at Top Butterley Farm
3.0 star property
9.0 out of 10, Wonderful, (2)
"The location is fine and the view beautiful. The owners were very helpful when needed. A most enjoyable stay."
Australia
Ian
The price is ₩596,847
₩596,847 total
includes taxes & fees
Dec 29 - Dec 30
Shire Cottage at Top Butterley Farm
Terrace/patio
2bed - Garden-pets-freeparking-m1connections

Residence in Chesterfield

2bed - Garden-pets-freeparking-m1connections
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 ₩175,445
₩210,534 total
includes taxes & fees
Dec 27 - Dec 28
2bed - Garden-pets-freeparking-m1connections
Terrace/patio
Five Acres

Cottage in Chesterfield

Five Acres
3.0 star property
The price is ₩6,884,344
₩8,261,213 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Five Acres
House | Exterior
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Residence in Chesterfield

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
The price is ₩236,858
₩331,674 total
includes taxes & fees
Dec 23 - Dec 24
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Cottage | 3 bedrooms, individually decorated, individually furnished, free WiFi
Cedar Cottage

Cottage in Chesterfield

Cedar Cottage
3.5 star property
The price is ₩635,159
₩762,191 total
includes taxes & fees
Dec 27 - Dec 28
Cedar Cottage
Fridge, microwave, oven, stovetop
a Quiet Semi Rural Property Located in Bolsover

Residence in Chesterfield

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
The price is ₩210,533
₩259,954 total
includes taxes & fees
Jan 2 - Jan 3, 2026
a Quiet Semi Rural Property Located in Bolsover
Cottage | Interior
Riber View Barn

Cottage in Chesterfield

Riber View Barn
3.5 star property
The price is ₩639,191
₩639,191 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Riber View Barn
Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher
Thorntree Lodge

Cottage in Chesterfield

Thorntree Lodge
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is ₩769,584
₩923,501 total
includes taxes & fees
Dec 28 - Dec 29
Thorntree Lodge
Cottage | Exterior
The Old Chapel

Cottage in Chesterfield

The Old Chapel
3.0 star property
10.0 out of 10, Exceptional, (2)
"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 ₩729,928
₩729,928 total
includes taxes & fees
Dec 28 - Dec 29
The Old Chapel
Cottage | Living room | TV
The Loft

Cottage in Chesterfield

The Loft
3.5 star property
The price is ₩998,106
₩1,197,727 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Loft
Living area
Overton

Cottage in Chesterfield

Overton
2.0 star property
The price is ₩946,017
₩1,135,220 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Overton
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cuckoo Nest

Cottage in Chesterfield

Cuckoo Nest
3.5 star property
The price is ₩549,463
₩659,356 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cuckoo Nest
Cottage | Outdoor dining
Moor Farm Cottage

Cottage in Chesterfield

Moor Farm Cottage
3.0 star property
The price is ₩1,003,147
₩1,203,776 total
includes taxes & fees
Dec 29 - Dec 30
Moor Farm Cottage
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

Leonardo Hotel Sheffield

Leonardo Hotel Sheffield

10/10 Excellent
"Nice room excellent location "
John 1-night trip
Posted 17 hours ago
Leonardo Hotel Sheffield

Find out more about Chesterfield

Search for Vacation rentals in Chesterfield on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chesterfield using one of the methods below:

  • View our selection of featured Vacation rentals in Chesterfield
  • Use the map to find apartments and other Vacation homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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 lively bars and top-notch restaurants. 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?

Studio Self contained flat free Parking: You might want to consider this vacation home rental near Chesterfield, which is near a train station and equipped with WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals will I find in Chesterfield?

With 36 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.