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

Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chesterfield holiday rentals

Private kitchen

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$794
HK$1,206 total
includes taxes & fees
2 Aug - 3 Aug
Commuters Getaway Chesterfield
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 HK$957
HK$1,167 total
includes taxes & fees
26 Jul - 27 Jul
2bed - garden-pets-freeparking-M1connections
Fridge, microwave, oven, stovetop

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is HK$1,061
HK$1,324 total
includes taxes & fees
26 Jul - 27 Jul
a quiet semi rural property located in bolsover
Outdoor spa tub

Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is HK$5,423
HK$6,507 total
includes taxes & fees
26 Jul - 27 Jul
Wigley Farm House Cottage
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 HK$3,821
HK$3,821 total
includes taxes & fees
20 Aug - 21 Aug
2 bedroom accommodation in Holymoorside
Outdoor dining

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
The price is HK$7,099
HK$7,099 total
includes taxes & fees
19 Aug - 20 Aug
Moor Farm Cottage near Ashover
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 HK$1,516
HK$1,726 total
includes taxes & fees
22 Jul - 23 Jul
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
WiFi

The Old Stables, Ashover

The Old Stables, Ashover
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"This was a perfect place for our family get together. Very clean, well appointed, and lovely location. The owner was also extremely helpful when one of our party had an accident and escorted us tothe nearest urfent care centre. Highly recommended."
United Kingdom
Duncan M.
The price is HK$11,856
HK$11,856 total
includes taxes & fees
29 Jul - 30 Jul
The Old Stables, Ashover
Exterior

Riber View Barn, Ashover

Riber View Barn, Ashover
Chesterfield
The price is HK$3,677
HK$3,677 total
includes taxes & fees
24 Jul - 25 Jul
Riber View Barn, Ashover
Outdoor dining

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is HK$5,825
HK$5,825 total
includes taxes & fees
9 Aug - 10 Aug
Bryn Tor - The Gardener's House
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 HK$794
HK$1,206 total
includes taxes & fees
23 Jul - 24 Jul
2bed - Garden-pets-freeparking-m1connections
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 HK$4,495
HK$4,495 total
includes taxes & fees
26 Jul - 27 Jul
Bathurst Cottage is a delightful three bedroom detached cottage.
3 bedrooms, free WiFi, individually decorated, individually furnished

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is HK$3,472
HK$4,166 total
includes taxes & fees
28 Jul - 29 Jul
Cedar Cottage
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 HK$1,261
HK$1,766 total
includes taxes & fees
28 Jul - 29 Jul
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Living area

Overton

Overton
2.0 star property
Chesterfield
The price is HK$5,038
HK$6,045 total
includes taxes & fees
2 Aug - 3 Aug
Overton
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 HK$1,065
HK$1,328 total
includes taxes & fees
27 Jul - 28 Jul
a Quiet Semi Rural Property Located in Bolsover
Property grounds

Little Mill

Little Mill
2.0 star property
Chesterfield
8.0 out of 10, Very good, (1 review)
"Lovely quiet place, the only downsides were, no outside seating area, or somewhere to loose your dog. There could be information about places of interest and walks. But overall we had a great holiday"
United Kingdom
Yvonne
The price is HK$2,926
HK$3,511 total
includes taxes & fees
27 Jul - 28 Jul
Little Mill
Outdoor dining

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is HK$5,485
HK$6,582 total
includes taxes & fees
4 Aug - 5 Aug
Moor Farm Cottage
Terrace/patio

Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is HK$5,727
HK$6,872 total
includes taxes & fees
31 Jul - 1 Aug
Cherry Tree Cottage
Exterior

Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is HK$2,837
HK$3,404 total
includes taxes & fees
28 Jul - 29 Jul
Riber View Barn
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

Hex Wildlife Hotel

Hex Wildlife Hotel

10/10 Excellent
"A modern fresh and clean hotel. Very quiet, really comfy beds, large television and a great assortment of tea and coffee options in the room Including tea bags, coffee bags, fruit tea and hot chocolate and biscuits. My one improvement would be to have the same extensive range of drinks at breakfast instead of just normal tea and various coffee options "
Peter 1-night trip
Posted 14 hours ago
Hex Wildlife 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:

  • 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 Clay Cross Active, 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 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 holiday rentals that Chesterfield has to offer?

2 Bed Derby House- Parking - Rolls Royce: This holiday home rental outside of Chesterfield offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Chesterfield?

With 45 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 Pomegranate Theatre and Barrow Hill Roundhouse Railway Centre. 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.