Search Holiday Rentals in Chesterfield

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
12 Jan - 13 Jan
Tomorrow
13 Jan - 14 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Chesterfield holiday rentals

Terrace/patio
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 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 3.124.809 ₫
3.749.771 ₫ total
includes taxes & fees
13 Jan - 14 Jan
2bed - Garden-pets-freeparking-m1connections
Cottage | Exterior
The Old Chapel

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 13.359.747 ₫
13.359.747 ₫ total
includes taxes & fees
15 Jan - 16 Jan
The Old Chapel
House | Private kitchen | Fridge, microwave, oven, stovetop
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 review)
The price is 3.093.708 ₫
4.134.958 ₫ total
includes taxes & fees
1 Feb - 2 Feb
2-bed House in Chesterfield Free Parking Garden
Cottage | Property grounds
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 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 10.917.642 ₫
10.917.642 ₫ total
includes taxes & fees
19 Jan - 20 Jan
Shire Cottage at Top Butterley Farm
House | 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 4.218.639 ₫
5.907.385 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Property grounds
Woodthorpe Cruck Cottage

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 18.315.782 ₫
21.978.938 ₫ total
includes taxes & fees
18 Jan - 19 Jan
Woodthorpe Cruck Cottage
Terrace/patio
Cherry Tree Cottage

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 19.153.759 ₫
22.984.511 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Cherry Tree Cottage
Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher
Thorntree Lodge

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is 14.095.969 ₫
16.915.163 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Thorntree Lodge
Cottage | 3 bedrooms, individually decorated, individually furnished, free WiFi
Cedar Cottage

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is 11.611.966 ₫
13.934.359 ₫ total
includes taxes & fees
19 Jan - 20 Jan
Cedar Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cuckoo Nest

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is 9.786.374 ₫
11.743.649 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Cuckoo Nest
Cottage | Interior
Riber View Barn

Riber View Barn

Riber View Barn
3.5 star property
Chesterfield
The price is 11.384.515 ₫
11.384.515 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Riber View Barn
Fridge, microwave, oven, stovetop
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 3.749.771 ₫
4.629.999 ₫ total
includes taxes & fees
13 Jan - 14 Jan
a Quiet Semi Rural Property Located in Bolsover
Living area
The Cottage

The Cottage

The Cottage
3.0 star property
Chesterfield
The price is 18.073.895 ₫
21.688.815 ₫ total
includes taxes & fees
15 Jan - 16 Jan
The Cottage
Cottage | Outdoor dining
Moor Farm Cottage

Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is 18.345.710 ₫
22.014.852 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Moor Farm Cottage
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

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

10/10 Excellent
"Took son to uni.Very comfortable stay. Excellent breakfast. "
Vishal 1-night trip
Posted 10 hours ago
The Orchard Hotel & Restaurant

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 top-notch restaurants and lively bars. Make sure you have time to check out the churches and parks during your trip.

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.