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Our top choices for Chesterfield holiday rentals

Cottage in Chesterfield

Cuckoo Nest
3.5 star property
The price is £330
includes taxes & fees
30 Mar - 31 Mar
Cuckoo Nest
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
The price is £100
includes taxes & fees
24 Mar - 25 Mar
2-bed House in Chesterfield Free Parking Garden
The price is £105
includes taxes & fees
24 Mar - 25 Mar
a quiet semi rural property located in bolsover

Cottage in Bolsover, near Chesterfield

Bryn Tor - The Gardener's House
The price is £505
includes taxes & fees
24 Mar - 25 Mar
Bryn Tor - The Gardener's House
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
24 Mar - 25 Mar
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
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 £389
includes taxes & fees
27 Mar - 28 Mar
Bathurst Cottage is a delightful three bedroom detached cottage.

Holiday Home in Chesterfield

Commuters Getaway 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
24 Mar - 25 Mar
Commuters Getaway Chesterfield
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 £287
includes taxes & fees
16 Apr - 17 Apr
2 bedroom accommodation in Holymoorside
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
26 Mar - 27 Mar
2bed - garden-pets-freeparking-M1connections

Cottage in Chesterfield

The Old Chapel
3.0 star property
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 £376
includes taxes & fees
27 Mar - 28 Mar
The Old Chapel
2.0 star property
The price is £163
includes taxes & fees
14 Apr - 15 Apr
Peak District - 2 Beds - Sleeps 4 - Pet Friendly
3.0 star property
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 £307
includes taxes & fees
27 Mar - 28 Mar
Shire Cottage at Top Butterley Farm

Cottage in Chesterfield

Cedar Cottage
3.5 star property
The price is £392
includes taxes & fees
30 Mar - 31 Mar
Cedar Cottage
2.0 star property
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 £87
includes taxes & fees
30 Mar - 31 Mar
2bed - Garden-pets-freeparking-m1connections

Cottage in Chesterfield

Cherry Tree Cottage
3.0 star property
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 £646
includes taxes & fees
29 Mar - 30 Mar
Cherry Tree Cottage

Cottage in Chesterfield

Harry's Lodge
3.0 star property
The price is £443
includes taxes & fees
27 Mar - 28 Mar
Harry's Lodge

Cottage in Chesterfield

The Cottage
3.0 star property
The price is £622
includes taxes & fees
27 Mar - 28 Mar
The Cottage

Cottage in Chesterfield

Moor Farm Cottage
3.0 star property
The price is £619
includes taxes & fees
1 Apr - 2 Apr
Moor Farm Cottage

Cottage in Chesterfield

Thorntree Lodge
3.5 star property
10.0 out of 10, Exceptional, (1 review)
The price is £476
includes taxes & fees
28 Mar - 29 Mar
Thorntree Lodge

Cottage in Chesterfield

The Loft at The George
3.5 star property
The price is £558
includes taxes & fees
27 Mar - 28 Mar
The Loft at The George
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 £50 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?

Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly: This holiday home rental outside of Chesterfield offers a private balcony, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Pomegranate Theatre. 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.