Chesterfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterfield holiday rentals

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 AU$760
includes taxes & fees
21 Jan - 22 Jan
The Old Chapel
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 AU$211
includes taxes & fees
22 Jan - 23 Jan
2bed - Garden-pets-freeparking-m1connections
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 AU$621
includes taxes & fees
21 Jan - 22 Jan
Shire Cottage at Top Butterley Farm
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is AU$229
includes taxes & fees
8 Feb - 9 Feb
2-bed House in Chesterfield Free Parking Garden

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 AU$1,304
includes taxes & fees
24 Jan - 25 Jan
Cherry Tree Cottage
2.0 star property
The price is AU$329
includes taxes & fees
29 Jan - 30 Jan
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Cottage in Chesterfield

The Old Grocery
3.5 star property
10.0 out of 10, Exceptional, (1 review)
The Old Grocery

Cottage in Chesterfield

Cuckoo Nest
3.5 star property
The price is AU$666
includes taxes & fees
7 Feb - 8 Feb
Cuckoo Nest

Cottage in Chesterfield

Thorntree Lodge
3.5 star property
10.0 out of 10, Exceptional, (1 review)
The price is AU$959
includes taxes & fees
20 Jan - 21 Jan
Thorntree Lodge

Cottage in Chesterfield

Woodthorpe Cruck Cottage
3.5 star property
9.0 out of 10, Wonderful, (2 reviews)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is AU$1,247
includes taxes & fees
29 Jan - 30 Jan
Woodthorpe Cruck Cottage

Cottage in Chesterfield

Riber View Barn
3.5 star property
The price is AU$646
includes taxes & fees
28 Jan - 29 Jan
Riber View Barn

Cottage in Chesterfield

Cedar Cottage
3.5 star property
The price is AU$792
includes taxes & fees
26 Jan - 27 Jan
Cedar Cottage
2.0 star property
The price is AU$257
includes taxes & fees
2 Feb - 3 Feb
a Quiet Semi Rural Property Located in Bolsover

Cottage in Chesterfield

The Tack Room Cottage
3.0 star property
The price is AU$1,133
includes taxes & fees
25 Jan - 26 Jan
The Tack Room Cottage

Cottage in Chesterfield

Harry's Lodge
3.0 star property
The price is AU$896
includes taxes & fees
25 Jan - 26 Jan
Harry's Lodge

Cottage in Chesterfield

Moor Farm Cottage
3.0 star property
The price is AU$1,249
includes taxes & fees
29 Jan - 30 Jan
Moor Farm Cottage

Cottage in Chesterfield

The Loft at The George
3.5 star property
The price is AU$1,124
includes taxes & fees
29 Jan - 30 Jan
The Loft at The George

Cottage in Chesterfield

Swallows Barn
3.5 star property
The price is AU$1,248
includes taxes & fees
30 Jan - 31 Jan
Swallows Barn

Cottage in Chesterfield

The Cottage
3.0 star property
The price is AU$1,233
includes taxes & fees
22 Jan - 23 Jan
The Cottage

Cottage in Chesterfield

The Old Stables
3.5 star property
The price is AU$1,460
includes taxes & fees
21 Jan - 22 Jan
The Old Stables
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 favourite 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 depend 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 AU$121 per night. Entering your travel dates in the search wizard might find you 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 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?

Oxton Hill Hideaway: This holiday home rental outside Chesterfield offers a terrace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Another good choice for your trip to Chesterfield is Rent My Spa Home with Pool table, Hottub and Sauna.

How many holiday rentals will I find in Chesterfield?

With 38 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.