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
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Chesterfield vacation rentals

Terrace/patio

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 ￥15,121
￥18,145 total
includes taxes & fees
Apr 22 - Apr 23
2bed - Garden-pets-freeparking-m1connections
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is ￥59,904
￥71,885 total
includes taxes & fees
Apr 20 - Apr 21
Cuckoo Nest
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 ￥31,035
￥35,345 total
includes taxes & fees
Apr 21 - Apr 22
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
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 ￥19,591
￥19,591 total
includes taxes & fees
Apr 20 - Apr 21
2bed - garden-pets-freeparking-M1connections
Fridge, microwave, oven, stovetop

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
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 ￥21,768
￥23,923 total
includes taxes & fees
May 3 - May 4
Commuters Getaway Chesterfield
Room

Riber View Barn, Ashover

Riber View Barn, Ashover
Chesterfield
The price is ￥73,103
￥73,103 total
includes taxes & fees
Apr 27 - Apr 28
Riber View Barn, Ashover
Living area

The Old Chapel, Handley

The Old Chapel, Handley
Chesterfield
The price is ￥85,787
￥85,787 total
includes taxes & fees
Apr 28 - Apr 29
The Old Chapel, Handley
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 ￥78,978
￥78,978 total
includes taxes & fees
May 4 - May 5
Bathurst Cottage is a delightful three bedroom detached cottage.
Room

Cherry Fields, Bolsover

Cherry Fields, Bolsover
Chesterfield
The price is ￥108,624
￥108,624 total
includes taxes & fees
Apr 18 - Apr 19
Cherry Fields, Bolsover
Outdoor dining

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is ￥114,281
￥114,281 total
includes taxes & fees
Apr 20 - Apr 21
Bryn Tor - The Gardener's House
House | Private kitchen | Fridge, microwave, oven, stovetop

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, (2 reviews)
The price is ￥15,609
￥21,317 total
includes taxes & fees
Apr 30 - May 1
2-bed House in Chesterfield Free Parking Garden
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 ￥81,778
￥81,778 total
includes taxes & fees
Apr 24 - Apr 25
The Old Chapel
Living area

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
The price is ￥141,363
￥141,363 total
includes taxes & fees
Apr 29 - Apr 30
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 ￥61,935
￥61,935 total
includes taxes & fees
Apr 17 - Apr 18
2 bedroom accommodation in Holymoorside
Living area

The Old Stables, Ashover

The Old Stables, Ashover
Chesterfield
The price is ￥164,885
￥164,885 total
includes taxes & fees
Apr 29 - Apr 30
The Old Stables, Ashover
Living area

The Cottage, Chesterfield

The Cottage, Chesterfield
Chesterfield
The price is ￥142,064
￥142,064 total
includes taxes & fees
Apr 20 - Apr 21
The Cottage, Chesterfield
Living area

Charming Tuliptree in Ashover

Charming Tuliptree in Ashover
Chesterfield
The price is ￥109,085
￥109,085 total
includes taxes & fees
Apr 19 - Apr 20
Charming Tuliptree in Ashover
Room

The Rumblings 3, Barlow

The Rumblings 3, Barlow
Dronfield
The price is ￥83,019
￥83,019 total
includes taxes & fees
Apr 25 - Apr 26
The Rumblings 3, Barlow
Fridge, microwave, oven, stovetop

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
Chesterfield
The price is ￥16,700
￥22,088 total
includes taxes & fees
Apr 23 - Apr 24
a Quiet Semi Rural Property Located in Bolsover
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 ￥70,786
￥70,786 total
includes taxes & fees
Apr 20 - Apr 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.
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

Buxton Crescent

Buxton Crescent

10/10 Excellent
"Beautiful well appointed hotel, with friendly and professional staff. Great restaurant ."
Phillip 2-night trip
Posted 3 hours ago
Buxton Crescent

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:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday 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 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 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 a TV and WiFi 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 37 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.