Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chesterfield holiday rentals

Private kitchen
2-bed House in Chesterfield Free Parking Garden

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, (1)
The price is RM485
RM648 total
includes taxes & fees
1 Jan - 2 Jan 2026
2-bed House in Chesterfield Free Parking Garden
Sauna
Five Acres

Five Acres

Five Acres
3.0 star property
Chesterfield
The price is RM19,038
RM22,845 total
includes taxes & fees
17 Jan - 18 Jan 2026
Five Acres
Private kitchen
2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
2.0 star property
Chesterfield
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 RM485
RM582 total
includes taxes & fees
9 Jan - 10 Jan 2026
2bed - Garden-pets-freeparking-m1connections
Interior
Riber View Barn

Riber View Barn

Riber View Barn
3.5 star property
Chesterfield
The price is RM1,768
RM1,768 total
includes taxes & fees
7 Jan - 8 Jan 2026
Riber View Barn
Exterior
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
Chesterfield
The price is RM655
RM917 total
includes taxes & fees
5 Jan - 6 Jan 2026
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Interior
The Loft

The Loft

The Loft
3.5 star property
Chesterfield
The price is RM2,760
RM3,312 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Loft
Property grounds
a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
Chesterfield
The price is RM582
RM719 total
includes taxes & fees
2 Jan - 3 Jan 2026
a Quiet Semi Rural Property Located in Bolsover
Private kitchen
Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
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 RM1,651
RM1,651 total
includes taxes & fees
3 Jan - 4 Jan 2026
Shire Cottage at Top Butterley Farm
Interior
Thorntree Lodge

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
The price is RM2,128
RM2,554 total
includes taxes & fees
2 Jan - 3 Jan 2026
Thorntree Lodge
Exterior
The Old Chapel

The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
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 RM2,074
RM2,074 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Old Chapel
Property grounds
Cedar Cottage

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is RM1,803
RM2,164 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cedar Cottage
Interior
The Old Stables

The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is RM3,322
RM3,987 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Old Stables
Living area
Overton

Overton

Overton
2.0 star property
Chesterfield
The price is RM2,616
RM3,139 total
includes taxes & fees
2 Jan - 3 Jan 2026
Overton
Exterior
Cuckoo Nest

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is RM1,482
RM1,779 total
includes taxes & fees
3 Jan - 4 Jan 2026
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

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

10/10 Excellent
"No breakfast taken during stay "
Rita 4-night trip
Posted 2 days ago
The Orchard Hotel & Restaurant

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia.co.uk! 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 holiday rental in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to The Herb Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Chesterfield has to offer?

Studio Self contained flat free Parking: This holiday home rental outside of Chesterfield is near a train station, and equipped with WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Amenities such as a microwave and free parking are also available for your convenience.

How many holiday rentals will I find in Chesterfield?

With 37 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chesterfield?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family getaway.