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

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Chesterfield vacation rentals

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 AED 1,840
AED 1,840 total
includes taxes & fees
4 Jul - 5 Jul
The Old Chapel
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 AED 566
AED 796 total
includes taxes & fees
19 Jul - 20 Jul
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Cottage | Outdoor spa tub

Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is AED 2,497
AED 2,997 total
includes taxes & fees
28 Jul - 29 Jul
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 AED 336
AED 520 total
includes taxes & fees
2 Jul - 3 Jul
2bed - Garden-pets-freeparking-m1connections
Cottage | Outdoor dining

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is AED 2,526
AED 3,031 total
includes taxes & fees
4 Jul - 5 Jul
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 AED 491
AED 612 total
includes taxes & fees
5 Jul - 6 Jul
a Quiet Semi Rural Property Located in Bolsover
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 AED 366
AED 555 total
includes taxes & fees
5 Jul - 6 Jul
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 AED 484
AED 581 total
includes taxes & fees
25 Jul - 26 Jul
2-bed House, Sleeps 4 w/ Parking & Garden
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 AED 1,592
AED 1,592 total
includes taxes & fees
7 Jul - 8 Jul
Shire Cottage at Top Butterley Farm
Dining

Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is AED 6,577
AED 7,892 total
includes taxes & fees
6 Jul - 7 Jul
Cherry Tree Farm
Living area

Overton

Overton
2.0 star property
Chesterfield
The price is AED 2,320
AED 2,784 total
includes taxes & fees
17 Jul - 18 Jul
Overton
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 AED 1,941
AED 2,329 total
includes taxes & fees
5 Jul - 6 Jul
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 AED 2,522
AED 3,026 total
includes taxes & fees
2 Jul - 3 Jul
Woodthorpe Cruck Cottage
Cottage | Property grounds

Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is AED 2,081
AED 2,497 total
includes taxes & fees
10 Jul - 11 Jul
Harry's Lodge
Cottage | Interior

Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is AED 2,518
AED 3,021 total
includes taxes & fees
17 Jul - 18 Jul
Swallows Barn
Exterior

Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is AED 1,306
AED 1,568 total
includes taxes & fees
24 Jul - 25 Jul
Riber View Barn
Cottage | Living room | TV

The Loft

The Loft
3.5 star property
Chesterfield
The price is AED 2,448
AED 2,937 total
includes taxes & fees
2 Jul - 3 Jul
The Loft
Fireplace

The Cottage

The Cottage
3.0 star property
Chesterfield
The price is AED 2,543
AED 3,051 total
includes taxes & fees
17 Jul - 18 Jul
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 AED 2,637
AED 3,165 total
includes taxes & fees
10 Jul - 11 Jul
Cherry Tree Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is AED 1,348
AED 1,617 total
includes taxes & fees
4 Jul - 5 Jul
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Palace Hotel & Spa Buxton

Palace Hotel & Spa Buxton

10/10 Excellent
"Weather was nice people nice location amazing around all the bars nice sights in the middle of every very good location"
chanice 2-night trip
Posted 9 hours ago
Palace Hotel & Spa Buxton

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.