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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Top Holiday Rentals in Chesterfield

Sauna
Five Acres

Cottage in Chesterfield

3.0 star property
The price is ₹417,698
₹501,238 total
includes taxes & fees
11 Dec - 12 Dec
Five Acres
House | Exterior
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Residence in Chesterfield

2.0 star property
The price is ₹14,227
₹19,952 total
includes taxes & fees
14 Dec - 15 Dec
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Cottage | Interior
Riber View Barn

Cottage in Chesterfield

3.5 star property
The price is ₹37,062
₹37,062 total
includes taxes & fees
14 Dec - 15 Dec
Riber View Barn
Cottage | Exterior
The Old Chapel

Cottage in Chesterfield

3.0 star property
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 ₹43,419
₹43,419 total
includes taxes & fees
12 Dec - 13 Dec
The Old Chapel
Cottage | Interior
Thorntree Lodge

Cottage in Chesterfield

3.5 star property
10.0 out of 10, Exceptional, (1)
The price is ₹45,778
₹54,933 total
includes taxes & fees
11 Dec - 12 Dec
Thorntree Lodge
Cottage | Property grounds
Cedar Cottage

Cottage in Chesterfield

3.5 star property
The price is ₹37,782
₹45,338 total
includes taxes & fees
12 Dec - 13 Dec
Cedar Cottage
Exterior
Cuckoo Nest

Cottage in Chesterfield

3.5 star property
The price is ₹31,884
₹38,262 total
includes taxes & fees
12 Dec - 13 Dec
Cuckoo Nest
Cottage | Private kitchen | Fridge, microwave, stovetop, cookware/dishes/utensils
Shire Cottage at Top Butterley Farm

Cottage in Chesterfield

3.0 star property
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 ₹35,503
₹35,503 total
includes taxes & fees
20 Dec - 21 Dec
Shire Cottage at Top Butterley Farm
Living area
Overton

Cottage in Chesterfield

2.0 star property
The price is ₹56,273
₹67,527 total
includes taxes & fees
12 Dec - 13 Dec
Overton
Fridge, dishwasher, cookware/dishes/utensils
Cherry Tree Cottage

Cottage in Chesterfield

3.0 star property
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 ₹62,970
₹75,563 total
includes taxes & fees
17 Dec - 18 Dec
Cherry Tree Cottage
Cottage | Exterior
Harry's Lodge

Cottage in Chesterfield

3.0 star property
The price is ₹40,981
₹49,176 total
includes taxes & fees
18 Dec - 19 Dec
Harry's Lodge
Cottage | Interior
The Loft at The George

Cottage in Chesterfield

3.5 star property
The price is ₹52,774
₹63,329 total
includes taxes & fees
15 Dec - 16 Dec
The Loft at The George
Cottage | Private kitchen | Dishwasher, high chair, cookware/dishes/utensils
The Old Grocery

Cottage in Chesterfield

3.5 star property
10.0 out of 10, Exceptional, (1)
The price is ₹51,695
₹51,695 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Old Grocery
Cottage | Interior
Woodthorpe Cruck Cottage

Cottage in Chesterfield

3.5 star property
9.0 out of 10, Wonderful, (2)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is ₹59,572
₹71,485 total
includes taxes & fees
11 Dec - 12 Dec
Woodthorpe Cruck Cottage
Cottage | Interior
The Old Stables

Cottage in Chesterfield

3.5 star property
The price is ₹69,467
₹83,360 total
includes taxes & fees
22 Dec - 23 Dec
The Old Stables
Cottage | Outdoor spa tub
Moor Farm Cottage

Cottage in Chesterfield

3.0 star property
The price is ₹59,671
₹71,605 total
includes taxes & fees
21 Dec - 22 Dec
Moor Farm Cottage
Cottage | Interior
Swallows Barn

Cottage in Chesterfield

3.5 star property
The price is ₹59,971
₹71,965 total
includes taxes & fees
19 Dec - 20 Dec
Swallows 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

Ensana Buxton Crescent

Ensana Buxton Crescent

10/10 Excellent
"Amazing room, great size, breakfast choice and food quality was good. Spa facilities justified the price. The spa was amazing with loads of small pools and 3 different sauna level and a steam room. It was out anniversary and they left 2 macaroons with a plate saying happy anniversary and a card which was a nice touch! "
Sam 2-night trip
Posted 2 days ago
Ensana Buxton Crescent

Find out more about Chesterfield

Holiday Rentals in 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 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?

Studio Self contained flat free Parking: This holiday home rental outside Chesterfield is near a train station, and equipped with free 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 35 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.