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 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chesterfield vacation rentals

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 P31,057
P31,057 total
includes taxes & fees
Jul 17 - Jul 18
The Old Chapel
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 P9,807
P13,733 total
includes taxes & fees
Jul 5 - Jul 6
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Outdoor spa tub

Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is P42,161
P50,593 total
includes taxes & fees
Jul 21 - Jul 22
Wigley Farm House Cottage
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 P6,134
P9,313 total
includes taxes & fees
Jul 8 - Jul 9
2bed - Garden-pets-freeparking-m1connections
Outdoor dining

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is P42,648
P51,177 total
includes taxes & fees
Jul 6 - Jul 7
Moor Farm Cottage
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 P8,228
P10,261 total
includes taxes & fees
Jul 10 - Jul 11
a Quiet Semi Rural Property Located in Bolsover
Private kitchen

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is P6,174
P9,373 total
includes taxes & fees
Jul 5 - Jul 6
Commuters Getaway Chesterfield
Living area

2-bed House, Sleeps 4 w/ Parking & Garden

2-bed House, Sleeps 4 w/ Parking & Garden
2.0 star property
Chesterfield
The price is P8,208
P9,850 total
includes taxes & fees
Jul 25 - Jul 26
2-bed House, Sleeps 4 w/ Parking & Garden
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 P26,883
P26,883 total
includes taxes & fees
Jul 7 - Jul 8
Shire Cottage at Top Butterley Farm
Dining

Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is P145,830
P174,995 total
includes taxes & fees
Jul 16 - Jul 17
Cherry Tree Farm
Living area

Overton

Overton
2.0 star property
Chesterfield
The price is P39,169
P47,003 total
includes taxes & fees
Jul 6 - Jul 7
Overton
Private kitchen

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is P32,769
P39,322 total
includes taxes & fees
Jul 6 - Jul 7
Thorntree Lodge
Property grounds

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 P42,578
P51,094 total
includes taxes & fees
Jul 9 - Jul 10
Woodthorpe Cruck Cottage
Property grounds

Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is P35,134
P42,161 total
includes taxes & fees
Jul 10 - Jul 11
Harry's Lodge
Interior

Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
Exterior

Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is P22,054
P26,465 total
includes taxes & fees
Jul 24 - Jul 25
Riber View Barn
Living room

The Loft

The Loft
3.5 star property
Chesterfield
The Loft
Fireplace

The Cottage

The Cottage
3.0 star property
Chesterfield
The price is P42,926
P51,511 total
includes taxes & fees
Jul 17 - Jul 18
The Cottage
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 P44,526
P53,432 total
includes taxes & fees
Jul 10 - Jul 11
Cherry Tree Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is P22,750
P27,300 total
includes taxes & fees
Jul 10 - Jul 11
Cuckoo Nest
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

Sandman Signature Sheffield Quays Hotel

Sandman Signature Sheffield Quays Hotel

8/10 Good
"No a/c so room was very warm and it wasn't a heatwave"
Caroline 2-night trip
Posted 2 hours ago
Sandman Signature Sheffield Quays Hotel

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 47 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.