A historic building with black and white timber framing, a prominent clock tower, and a pointed spire in the background.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chesterfield vacation rentals

Terrace/patio

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 ￥15,243
￥23,506 total
includes taxes & fees
Jul 17 - Jul 18
2bed - Garden-pets-freeparking-m1connections
Fridge, microwave, oven, stovetop

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is ￥21,901
￥27,333 total
includes taxes & fees
Jul 29 - Jul 30
a quiet semi rural property located in bolsover
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is ￥60,392
￥72,470 total
includes taxes & fees
Jul 20 - Jul 21
Cuckoo Nest
WiFi

The Old Stables, Ashover

The Old Stables, Ashover
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"This was a perfect place for our family get together. Very clean, well appointed, and lovely location. The owner was also extremely helpful when one of our party had an accident and escorted us tothe nearest urfent care centre. Highly recommended."
United Kingdom
Duncan M.
The price is ￥170,888
￥170,888 total
includes taxes & fees
Jul 20 - Jul 21
The Old Stables, Ashover
Exterior

Riber View Barn, Ashover

Riber View Barn, Ashover
Chesterfield
The price is ￥75,764
￥75,764 total
includes taxes & fees
Jul 28 - Jul 29
Riber View Barn, Ashover
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 ￥19,950
￥24,339 total
includes taxes & fees
Jul 17 - Jul 18
2bed - garden-pets-freeparking-M1connections
Outdoor dining

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
The price is ￥146,509
￥146,509 total
includes taxes & fees
Jul 22 - Jul 23
Moor Farm Cottage near Ashover
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 ￥74,526
￥74,526 total
includes taxes & fees
Aug 8 - Aug 9
2 bedroom accommodation in Holymoorside
Outdoor dining

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is ￥120,219
￥120,219 total
includes taxes & fees
Jul 29 - Jul 30
Bryn Tor - The Gardener's House
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 ￥89,735
￥89,735 total
includes taxes & fees
Jul 31 - Aug 1
Bathurst Cottage is a delightful three bedroom detached cottage.
House | Private kitchen | Fridge, microwave, oven, stovetop

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥16,555
￥25,133 total
includes taxes & fees
Aug 2 - Aug 3
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 ￥31,603
￥35,992 total
includes taxes & fees
Jul 22 - Jul 23
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Exterior

Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is ￥58,545
￥70,254 total
includes taxes & fees
Jul 28 - Jul 29
Riber View Barn
House | Exterior

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
3.0 star property
Chesterfield
The price is ￥25,512
￥35,830 total
includes taxes & fees
Jul 28 - Jul 29
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
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 Old Chapel
Fridge, microwave, oven, stovetop

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is ￥21,984
￥27,416 total
includes taxes & fees
Jul 28 - Jul 29
a Quiet Semi Rural Property Located in Bolsover
Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is ￥86,986
￥104,383 total
includes taxes & fees
Jul 20 - Jul 21
Thorntree Lodge
Property grounds

Little Mill

Little Mill
2.0 star property
Chesterfield
8.0 out of 10, Very Good, (1 review)
"Lovely quiet place, the only downsides were, no outside seating area, or somewhere to loose your dog. There could be information about places of interest and walks. But overall we had a great holiday"
United Kingdom
Yvonne
The price is ￥60,392
￥72,470 total
includes taxes & fees
Jul 28 - Jul 29
Little Mill
Cottage | Outdoor spa tub

Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is ￥113,047
￥135,656 total
includes taxes & fees
Jul 21 - Jul 22
Wigley Farm House Cottage
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 ￥73,578
￥73,578 total
includes taxes & fees
Jul 20 - Jul 21
Shire Cottage at Top Butterley Farm
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
"Absolutely as you'd expect from a brand new hotel. The location is fantastic for any Sheffield stay and is now the top recommendation to delegates as we run conferences from work. Reception staff in particular were really helpful."
Andrew 1-night trip
Posted less than an hour ago
Radisson Blu Hotel, Sheffield

Find out more about Chesterfield

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

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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 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?

2 Bed Derby House- Parking - Rolls Royce: You might want to consider this vacation home rental near Chesterfield, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Chesterfield?

With 50 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 Chesterfield Museum & Art Gallery. 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.