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Our top choices for Chesterfield holiday rentals

2-bed House in Chesterfield Free Parking Garden

2-bed House in Chesterfield Free Parking Garden
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is £99
includes taxes & fees
11 May - 12 May
2-bed House in Chesterfield Free Parking Garden

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is £334
includes taxes & fees
13 May - 14 May
Cuckoo Nest

Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
Chesterfield
6.0 out of 10, (1 review)
"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 £101
includes taxes & fees
11 May - 12 May
Commuters Getaway Chesterfield

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 £164
includes taxes & fees
10 May - 11 May
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Riber View Barn, Ashover

Riber View Barn, Ashover
Chesterfield
The price is £339
includes taxes & fees
27 May - 28 May
Riber View Barn, Ashover

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 £91
includes taxes & fees
10 May - 11 May
2bed - garden-pets-freeparking-M1connections

The Old Chapel, Handley

The Old Chapel, Handley
Chesterfield
The price is £398
includes taxes & fees
10 May - 11 May
The Old Chapel, Handley

Cherry Fields, Bolsover

Cherry Fields, Bolsover
Chesterfield
The price is £555
includes taxes & fees
1 Jun - 2 Jun
Cherry Fields, Bolsover

Moor Farm Cottage near Ashover

Moor Farm Cottage near Ashover
Chesterfield
The price is £656
includes taxes & fees
22 May - 23 May
Moor Farm Cottage near Ashover

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 £309
includes taxes & fees
9 May - 10 May
2 bedroom accommodation in Holymoorside

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 £91
includes taxes & fees
10 May - 11 May
2bed - Garden-pets-freeparking-m1connections

Little Mill

Little Mill
2.0 star property
Chesterfield
The price is £334
includes taxes & fees
22 May - 23 May
Little Mill

The Rumblings 3, Barlow

The Rumblings 3, Barlow
Dronfield
The price is £385
includes taxes & fees
10 May - 11 May
The Rumblings 3, Barlow

Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is £556
includes taxes & fees
18 May - 19 May
Bryn Tor - The Gardener's House

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 £765
includes taxes & fees
11 May - 12 May
The Old Stables, Ashover

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 £380
includes taxes & fees
4 Jun - 5 Jun
Bathurst Cottage is a delightful three bedroom detached cottage.

Charming Tuliptree in Ashover

Charming Tuliptree in Ashover
Chesterfield
The price is £340
includes taxes & fees
6 Jun - 7 Jun
Charming Tuliptree in Ashover

The Cottage, Chesterfield

The Cottage, Chesterfield
Chesterfield
The price is £660
includes taxes & fees
29 May - 30 May
The Cottage, Chesterfield

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
3.0 star property
Chesterfield
The price is £165
includes taxes & fees
10 May - 11 May
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Riber View Barn

Riber View Barn
2.0 star property
Chesterfield
The price is £323
includes taxes & fees
5 Jun - 6 Jun
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

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as £59 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .: This holiday home rental outside of Chesterfield offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and an oven.

How many holiday rentals will I find in Chesterfield?

With 43 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 Chesterfield Museum & Art Gallery 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.