Chesterfield District Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Holiday Rentals Destinations in Chesterfield District

1-bed Apt, Sleeps 2, 20 Mins to Peak District

3.0 star property
The price is NZ$227
includes taxes & fees
23 Sept - 24 Sept
1-bed Apt, Sleeps 2, 20 Mins to Peak District

KSpace @ The Point

3.5 star property
9.6 out of 10, Exceptional, (51)
"Everything I needed was there. Great location. Excellent overall."
KSpace @ The Point

5* Detached Stone Cottage with a Private Indoor Pool (Not Shared)

10.0 out of 10, Exceptional, (248)
"Absolutely wonderful pool. Owners were incredibly nice. Some very good walks nearby"
5* Detached Stone Cottage with a Private Indoor Pool (Not Shared)

The Nest

3.5 star property
6.4 out of 10, (15)
"Excellent location, specious flat, will definitely book again!"
The Nest

Three Cranes Serviced Apartments

3.5 star property
8.4 out of 10, Very good, (124)
"Great place to stay"
Three Cranes Serviced Apartments

Spacesavers

3.5 star property
8.2 out of 10, Very good, (54)
"Quirky set up, very central to Sheffield which was great, bare essentials but everything works"
The price is NZ$166
includes taxes & fees
1 Oct - 2 Oct
Spacesavers

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

9.8 out of 10, Exceptional, (18)
"We loved our stay the Hay Barn. Perfect size and location for our family getaway. Hosts were friendly and helpful. The area is a firm favourite for us, plenty of lovely towns and activities to do . We would definitely rebook in the future."
Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

Stay Angels Blonk Street Apartments

3.0 star property
6.0 out of 10, (2)
"The apartment was clean, quiet, and overall very good shape. "
The price is NZ$355
includes taxes & fees
21 Sept - 22 Sept
Stay Angels Blonk Street Apartments

The Sinclair Building

4.0 star property
9.2 out of 10, Wonderful, (52)
"Nice property. Well maintained. Surrounding area very dirty and felt unsafe. Noisy at night. "
The Sinclair Building

Hollis Croft

2.0 star property
6.0 out of 10, (4)
"Excellent studio apartment with all the facilities you'd need for a short stay, in a clean, modern building and at a great price. Great central location and good for trams, especially if travelling to Tramlines festival. Lots of extra facilities in building like a laundry room which was very useful. Would definitely stay again next time in Sheffield."
Hollis Croft

Padley Farm

2.0 star property
9.6 out of 10, Exceptional, (124)
"A great place to stay in a picturesque environment. Peaceful and relaxing. A great base to go into Sheffield or visit any of the historic sites in the Peak District. What an incredibly beautiful area! We would come back in a heartbeat! "
Padley Farm

Bailey Fields

2.0 star property
4.0 out of 10, (1)
"Bed was very uncomfortable and they gave us a key that didn’t work to the front door of the building. Was woken up early morning by the cleaner so had to check out earlier than implied. Won’t be coming back "
Bailey Fields

Gratton Grange Farm Holiday Cottage

3.0 star property
9.2 out of 10, Wonderful, (51)
"Excellent stay. Would definitely stay again. "
Gratton Grange Farm Holiday Cottage

Corner House in Sheffield

2.0 star property
Corner House in Sheffield

AWESOME 1 Bedroom Flat in Doncaster 2

2.0 star property
2.0 out of 10, (2)
"The host ignored my calls and I was left stranded after calling numerous times, they switched their phone off. I want a refund as I had to book alternative accommodation. Very disappointed"
AWESOME 1 Bedroom Flat in Doncaster 2

Student Only Straits Manor

3.0 star property
Student Only Straits Manor

Sheffield Hillside Retreat

3.5 star property
The price is NZ$293
includes taxes & fees
21 Sept - 22 Sept
Sheffield Hillside Retreat

Oakerthorpe Holiday Village

4.5 star property
10.0 out of 10, Exceptional, (3)
"Absolutely beautiful cottage full of essentials for our stay. The whole setting is stunning with the gardens and surrounding areas. Plenty of local pubs and restaurants close by for food as well as supermarkets to grab snacks for the house. We went to Gulliver’s kingdom 20 mins away and Alton towers 1 hour away across our 2 days stay which were both easily accessible. There is a wide range of sizes of cottage and homes to choose from all of which looked amazing. "
Oakerthorpe Holiday Village

Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

8.0 out of 10, Very good, (13)
"Had a great time celebrating a joint 40th. Lots of room and great location. All nice and easy with the host. Perfect!"
Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

Newly refurbished luxury 5 bed riverside house with hot tub and annexe.

10.0 out of 10, Exceptional, (41)
"Beautiful property, very well equipped. Loved our stay!"
Newly refurbished luxury 5 bed riverside house with hot tub and annexe.
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 District Hotel Reviews

Find out more about Chesterfield District

Find out more about Chesterfield District

Everything you need to know about Chesterfield District 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 District 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 District holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield District holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield District. 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 District 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 District holiday rentals we have selected for you start as low as NZ$166 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield District rentals

At Expedia, we put the best Chesterfield District 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 District 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 District 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 District. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia