Chesterfield Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chesterfield holiday rentals

Sauna
Five Acres

Five Acres

Five Acres
3.0 star property
Chesterfield
The price is HK$36,495
HK$43,794 total
includes taxes & fees
20 Jan - 21 Jan 2026
Five Acres
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 HK$907
HK$1,215 total
includes taxes & fees
3 Jan - 4 Jan 2026
2-bed House in Chesterfield Free Parking Garden
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
Chesterfield
The price is HK$1,121
HK$1,383 total
includes taxes & fees
6 Jan - 7 Jan 2026
a quiet semi rural property located in bolsover
Fridge, microwave, oven, stovetop
2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
The price is HK$1,121
HK$1,121 total
includes taxes & fees
1 Jan - 2 Jan 2026
2bed - garden-pets-freeparking-M1connections
Fridge, microwave, oven, stovetop
2br-towncentre-garden-freeparking-pets

2br-towncentre-garden-freeparking-pets

2br-towncentre-garden-freeparking-pets
Chesterfield
6.0 out of 10, (1)
"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 HK$1,121
HK$1,226 total
includes taxes & fees
1 Jan - 2 Jan 2026
2br-towncentre-garden-freeparking-pets
Property grounds
2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (4)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
The price is HK$2,997
HK$2,997 total
includes taxes & fees
4 Jan - 5 Jan 2026
2 bedroom accommodation in Holymoorside
Property grounds
Bathurst Cottage is a delightful three bedroom detached cottage.

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)
"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 HK$3,060
HK$3,060 total
includes taxes & fees
16 Jan - 17 Jan 2026
Bathurst Cottage is a delightful three bedroom detached cottage.
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
Chesterfield
10.0 out of 10, Exceptional, (1)
"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 HK$1,509
HK$1,719 total
includes taxes & fees
5 Jan - 6 Jan 2026
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Living area
Overton

Overton

Overton
2.0 star property
Chesterfield
The price is HK$5,015
HK$6,018 total
includes taxes & fees
4 Jan - 5 Jan 2026
Overton
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 HK$930
HK$1,116 total
includes taxes & fees
11 Jan - 12 Jan 2026
2bed - Garden-pets-freeparking-m1connections
Fridge, dishwasher, cookware/dishes/utensils
Cherry Tree Cottage

Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
"Everything was fantastic, fell in love witj the cottage , peaceful , perfect, I will come back again . Love it "
United Kingdom
toyin
The price is HK$5,701
HK$6,841 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cherry Tree Cottage
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 HK$1,243
HK$1,744 total
includes taxes & fees
6 Jan - 7 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 HK$5,291
HK$6,349 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Loft
Interior
Thorntree Lodge

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
The price is HK$4,196
HK$5,035 total
includes taxes & fees
4 Jan - 5 Jan 2026
Thorntree Lodge
Interior
Swallows Barn

Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is HK$5,443
HK$6,531 total
includes taxes & fees
5 Jan - 6 Jan 2026
Swallows Barn
Interior
Riber View Barn

Riber View Barn

Riber View Barn
3.5 star property
Chesterfield
The price is HK$3,388
HK$3,388 total
includes taxes & fees
7 Jan - 8 Jan 2026
Riber View Barn
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 HK$3,976
HK$3,976 total
includes taxes & fees
10 Jan - 11 Jan 2026
The Old Chapel
Interior
The Old Stables

The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is HK$6,369
HK$7,643 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Old Stables
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 HK$1,088
HK$1,350 total
includes taxes & fees
5 Jan - 6 Jan 2026
a Quiet Semi Rural Property Located in Bolsover
Exterior
Cuckoo Nest

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is HK$2,913
HK$3,495 total
includes taxes & fees
4 Jan - 5 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.
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

B&B HOTEL Derby

B&B HOTEL Derby

10/10 Excellent
"Modern hotel close to the railway station. Clean, comfortable, well appointed. Staff I encountered were excellent."
Alan 1-night trip
Posted 2 days ago
B&B HOTEL Derby

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 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.