Chesterfield Holiday Rentals

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
  • 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

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)
The price is NZ$268
includes taxes & fees
1 Jan - 2 Jan 2026
2-bed House in Chesterfield Free Parking Garden

Five Acres

Five Acres
3.0 star property
Chesterfield
The price is NZ$9,665
includes taxes & fees
17 Jan - 18 Jan 2026
Five Acres

a quiet semi rural property located in bolsover

a quiet semi rural property located in bolsover
Chesterfield
The price is NZ$305
includes taxes & fees
3 Jan - 4 Jan 2026
a quiet semi rural property located in bolsover

2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
The price is NZ$247
includes taxes & fees
1 Jan - 2 Jan 2026
2bed - garden-pets-freeparking-M1connections

2br-towncentre-garden-freeparking-pets

2br-towncentre-garden-freeparking-pets
Chesterfield
6.0 out of 10, (1)
"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 NZ$271
includes taxes & fees
1 Jan - 2 Jan 2026
2br-towncentre-garden-freeparking-pets

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
Chesterfield
10.0 out of 10, Exceptional, (1)
"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 NZ$379
includes taxes & fees
5 Jan - 6 Jan 2026
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (4)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
The price is NZ$661
includes taxes & fees
4 Jan - 5 Jan 2026
2 bedroom accommodation in Holymoorside

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)
"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 NZ$675
includes taxes & fees
18 Jan - 19 Jan 2026
Bathurst Cottage is a delightful three bedroom detached cottage.

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
2.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
"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 NZ$246
includes taxes & fees
1 Jan - 2 Jan 2026
2bed - Garden-pets-freeparking-m1connections

Riber View Barn

Riber View Barn
3.5 star property
Chesterfield
The price is NZ$748
includes taxes & fees
7 Jan - 8 Jan 2026
Riber View Barn

Peak District - 2 Beds - Sleeps 4 - Pet Friendly

Peak District - 2 Beds - Sleeps 4 - Pet Friendly
2.0 star property
Chesterfield
The price is NZ$385
includes taxes & fees
5 Jan - 6 Jan 2026
Peak District - 2 Beds - Sleeps 4 - Pet Friendly

The Loft

The Loft
3.5 star property
Chesterfield
The price is NZ$1,401
includes taxes & fees
6 Jan - 7 Jan 2026
The Loft

a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
2.0 star property
Chesterfield
The price is NZ$298
includes taxes & fees
3 Jan - 4 Jan 2026
a Quiet Semi Rural Property Located in Bolsover

Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
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 NZ$717
includes taxes & fees
4 Jan - 5 Jan 2026
Shire Cottage at Top Butterley Farm

Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
The price is NZ$1,081
includes taxes & fees
2 Jan - 3 Jan 2026
Thorntree Lodge

The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
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 NZ$855
includes taxes & fees
4 Jan - 5 Jan 2026
The Old Chapel

Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is NZ$915
includes taxes & fees
7 Jan - 8 Jan 2026
Cedar Cottage

The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is NZ$1,687
includes taxes & fees
5 Jan - 6 Jan 2026
The Old Stables

Overton

Overton
2.0 star property
Chesterfield
The price is NZ$1,328
includes taxes & fees
6 Jan - 7 Jan 2026
Overton

Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is NZ$753
includes taxes & fees
3 Jan - 4 Jan 2026
Cuckoo Nest
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 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 NZ$136 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 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 lively bars and top-notch restaurants. 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 of Chesterfield is near a train station, and equipped with 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 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.