A town with a prominent church spire, residential buildings, and a hill in the background.

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

1. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Westport
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic place!"
United States
Anonymous traveller
The price is NZ$119
includes taxes & fees
30 Aug - 31 Aug
2 Queen Beds | Non-Smoking, Kitchen

2. Stunning Minimalist Gem | Fenced Backyard + W/D

Stunning Minimalist Gem | Fenced Backyard + W/D
Princeton Heights
10.0 out of 10, Exceptional, (22 reviews)
"I think the best part was that there were little hidden restaurants well within walking distance. It was an excellent stay, the accommodation were cozy."
United States
christine
The price is NZ$302
includes taxes & fees
24 Aug - 25 Aug
Stunning Minimalist Gem | Fenced Backyard + W/D

3. Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.2 out of 10, Wonderful, (21 reviews)
"Great location, responsive host & perfect for our short stay! "
United States
Bekah K.
The price is NZ$313
includes taxes & fees
23 Aug - 24 Aug
Charming Tower Grove Flat-Steps to T.G Park+Grand

4. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (185 reviews)
"Great place to stay. Our go to when visiting St.Charles or STL"
United States
jeramy p.
The price is NZ$434
includes taxes & fees
23 Aug - 24 Aug
The Lofts of North Main Street

5. Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (170 reviews)
"Great place!"
United States
Arthur S.
The price is NZ$256
includes taxes & fees
26 Aug - 27 Aug
Centrally located in the Tower Grove East neighborhood!

6. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (152 reviews)
"Staff was great and accommodating to my needs."
United States
Triman
The price is NZ$212
includes taxes & fees
23 Aug - 24 Aug
White House at Grand Central

7. Historic 1805 Main Street 2BR

Historic 1805 Main Street 2BR
St. Charles Historic District
9.6 out of 10, Exceptional, (42 reviews)
"The location is excellent. "
United States
McRay H.
The price is NZ$543
includes taxes & fees
24 Aug - 25 Aug
Historic 1805 Main Street 2BR

8. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (9 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
The price is NZ$484
includes taxes & fees
25 Aug - 26 Aug
Cottage on Main st- Low Cleaning Fee

9. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (68 reviews)
"Lovely accommodations, very clean, well equipped, great location. "
United States
Emily B.
The price is NZ$434
includes taxes & fees
23 Aug - 24 Aug
Amazing Renovated Historic Loft on Main Street

10. Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
8.6 out of 10, Excellent, (18 reviews)
"Clean, convenient and satisfied our needs for this stay. "
United States
Michael L.
The price is NZ$471
includes taxes & fees
23 Aug - 24 Aug
Settle into Soulard! 6 beds 2 full baths!

11. Urban Loft near Soulard and Free Parking

Urban Loft near Soulard and Free Parking
Benton Park West
9.6 out of 10, Exceptional, (75 reviews)
"It was a nice cozy place! Good price for the money, bed was very comfortable! "
United States
Luke S.
The price is NZ$209
includes taxes & fees
1 Sept - 2 Sept
Urban Loft near Soulard and Free Parking

12. 6649 2E | Boutique Hotel Studio in Forest Park

6649 2E | Boutique Hotel Studio in Forest Park
Dogtown
8.0 out of 10, Very good, (16 reviews)
"Friendly staff helped with my booking, check in was easy. Would stay again! "
United States
Marie
The price is NZ$239
includes taxes & fees
24 Aug - 25 Aug
6649 2E | Boutique Hotel Studio in Forest Park

13. TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
Skinker DeBaliviere
9.8 out of 10, Exceptional, (17 reviews)
"Very family-friendly area and great location."
United States
Krystle D.
The price is NZ$554
includes taxes & fees
22 Aug - 23 Aug
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

14. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"The apartment was conveniently located within walking distance of many attractions in Forest Park, and several bus lines for those who are inclined to explore the city via public transit. The apartment provided a good amount of space for two people. We really appreciated the free passes that were offered. We did, however, experience a number of issues during our stay. One warning to potential renters: if you need a quiet bedroom for sleeping, this may not be the property for you. Both the wood...
United States
Susan
The price is NZ$252
includes taxes & fees
24 Aug - 25 Aug
6653 2S | Jewel of Central St. Louis

15. Historic Main Street Studio | Dog-Friendly

Historic Main Street Studio | Dog-Friendly
St. Charles Historic District
9.2 out of 10, Wonderful, (37 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
The price is NZ$407
includes taxes & fees
1 Sept - 2 Sept
Historic Main Street Studio | Dog-Friendly

16. Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (8 reviews)
"The host was very responsive to all communication and our stay was very nice. It was a nice place to stay. It was comfortable and met are needs very well."
United States
Denise S.
The price is NZ$183
includes taxes & fees
26 Aug - 27 Aug
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

17. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (116 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is NZ$434
includes taxes & fees
24 Aug - 25 Aug
Prime Loft of Main Street

18. Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (25 reviews)
"Brandon was awesome and the neighborhood is fun with lots of terrific restaurants. "
United States
Leslie H.
The price is NZ$302
includes taxes & fees
24 Aug - 25 Aug
Elegant Minimalist Gem w/ Private backyard, W/D

19. 6647 1W | Quaint Studio in Central St. Louis

6647 1W | Quaint Studio in Central St. Louis
Dogtown
8.2 out of 10, Very good, (28 reviews)
"Great location, secure parking, overall great stay "
United States
Marcus
The price is NZ$235
includes taxes & fees
31 Aug - 1 Sept
6647 1W | Quaint Studio in Central St. Louis

20. Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful, peaceful stay!"
United States
Robin
The price is NZ$345
includes taxes & fees
26 Aug - 27 Aug
Classy Midtown 2BR, King Master
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, 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$119 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 holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sophia M. Sachs Butterfly House, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

4BR 2BA Modern Family Home with Private Heated Inground Pool Open March 1-Nov11: This holiday home rental outside of Chesterfield offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chesterfield?

Choose from 8 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Sophia M. Sachs Butterfly House and Missouri River are a couple of great spots to enjoy the outdoors. Other places in town to visit include The Factory and St. Louis Premium Outlets.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.