Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Chesterfield holiday rentals

Interior

3+ acres, fast wi-fi, garage parking, Koi pond

3+ acres, fast wi-fi, garage parking, Koi pond
Wildwood
The price is HK$1,509
HK$3,015 total
includes taxes & fees
2 Jun - 3 Jun
3+ acres, fast wi-fi, garage parking, Koi pond
Interior

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
8.4 out of 10, Very good, (18 reviews)
"We only stayed one day and did not spend a whole lot of time in the cabin, but it was quaint and comfortable. In a perfect world it would have been priced a bit less (since it was the off season for wine country) but we enjoyed it either way."
United States
Doug S.
The price is HK$829
HK$1,790 total
includes taxes & fees
3 Jun - 4 Jun
Adorable Augusta Cabin
Interior

Walk to Bars & Dining: Historic Benton Park Gem

Walk to Bars & Dining: Historic Benton Park Gem
3.0 star property
Benton Park
The price is HK$768
HK$2,187 total
includes taxes & fees
3 Jun - 4 Jun
Walk to Bars & Dining: Historic Benton Park Gem
Property grounds

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, (7 reviews)
"The host responded quickly and was attentive to our needs. "
United States
Caren L.
The price is HK$564
HK$889 total
includes taxes & fees
2 Jun - 3 Jun
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
1 bedroom, free WiFi

6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is HK$549
HK$1,097 total
includes taxes & fees
1 Jun - 2 Jun
6649 1E | Garden Style Studio Near Forest Park
Dining

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, (157 reviews)
"Place was incredibly clean and setup was very conducive to a nice stay. We appreciated the opportunity to stay at such a nice place. "
United States
Jerry D.
The price is HK$529
HK$1,201 total
includes taxes & fees
31 May - 1 Jun
Centrally located in the Tower Grove East neighborhood!
Fridge, microwave, oven, stovetop

Settle into Soulard! 6 beds 2 full baths!

Settle into Soulard! 6 beds 2 full baths!
Soulard
9.2 out of 10, Wonderful, (9 reviews)
"Great location in Soulard if you want to be there but keep the core activities at arms length. The apartment is roomy enough for a big group to feel comfortable."
United States
John M.
The price is HK$431
HK$2,217 total
includes taxes & fees
3 Jun - 4 Jun
Settle into Soulard! 6 beds 2 full baths!
Fridge, microwave, oven, stovetop

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (49 reviews)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is HK$1,089
HK$2,288 total
includes taxes & fees
14 Jun - 15 Jun
Convenience 2 Bedroom House to Explore All of St Louis
Interior

Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a short get away"
United States
andytrower U.
The price is HK$913
HK$1,608 total
includes taxes & fees
7 Jun - 8 Jun
Adorable small house - quiet & safe - 2 BR 1 Bath
Bar (on property)

Aspen Heights by Innsbrook Vacations!

Aspen Heights by Innsbrook Vacations!
Innsbrook
9.0 out of 10, Wonderful, (10 reviews)
"Nice, quiet, relaxing place to stay! Great communication with the host. "
United States
Lorna M.
The price is HK$598
HK$1,781 total
includes taxes & fees
31 May - 1 Jun
Aspen Heights by Innsbrook Vacations!
Dining

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, (19 reviews)
"Great location. Long term stay was excellent!"
United States
Shay W.
The price is HK$580
HK$1,559 total
includes taxes & fees
3 Jun - 4 Jun
Charming Tower Grove Flat-Steps to T.G Park+Grand
2 bedrooms, iron/ironing board, WiFi, bed sheets

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, (15 reviews)
"Nice property and nice location."
United States
Richard B.
The price is HK$815
HK$2,661 total
includes taxes & fees
31 May - 1 Jun
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
Fridge, microwave, oven, stovetop

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (47 reviews)
"Our host Bonnie was very welcoming and accommodating great location, we enjoyed every minute and are so grateful."
United States
Lisa Ann J.
The price is HK$776
HK$1,821 total
includes taxes & fees
3 Jun - 4 Jun
Top of Geyer apartment
TV, offices

Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.8 out of 10, Good, (11 reviews)
"We enjoyed our stay"
United States
Dee
The price is HK$415
HK$1,348 total
includes taxes & fees
31 May - 1 Jun
Safe and private apt-Near Forest Park-Free parking
TV

6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (24 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
The price is HK$627
HK$1,175 total
includes taxes & fees
1 Jun - 2 Jun
6655 1N | Elegance Near the St. Louis Arch
Interior

Spacious, cozy home in Saint Louis

Spacious, cozy home in Saint Louis
St. Louis
10.0 out of 10, Exceptional, (31 reviews)
"Great stay. Location was perfect and quiet. Gracious Host. Would stay again!!!!"
United States
Gerald B.
The price is HK$1,375
HK$2,209 total
includes taxes & fees
31 May - 1 Jun
Spacious, cozy home in Saint Louis
Bar (on property)

Lake Aspen Landing by Innsbrook Vacations!

Lake Aspen Landing by Innsbrook Vacations!
Innsbrook
9.0 out of 10, Wonderful, (14 reviews)
"We had a relaxing enjoyable stay at the condo and would definitely return to Innsbrook in the future"
United Kingdom
Anthony H.
The price is HK$573
HK$1,776 total
includes taxes & fees
10 Jun - 11 Jun
Lake Aspen Landing by Innsbrook Vacations!
Terrace/patio

WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL

WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL
Augusta
10.0 out of 10, Exceptional, (34 reviews)
"Adorable place to stay!"
United States
Amy F.
The price is HK$1,277
HK$2,313 total
includes taxes & fees
1 Jun - 2 Jun
WELCOME TO THE OWL'S NEST - 2 BEDROOM HOME IN AUGUSTA, WINERIES & THE KATY TRAIL
Bar (on property)

Serene Seebach Sights by Innsbrook Vacations!

Serene Seebach Sights by Innsbrook Vacations!
Innsbrook
9.4 out of 10, Exceptional, (10 reviews)
"Great clubhouse, plenty of wildlife roaming grounds, and friendly atmosphere."
United States
tony
The price is HK$564
HK$1,735 total
includes taxes & fees
31 May - 1 Jun
Serene Seebach Sights by Innsbrook Vacations!
Smart TV, fireplace, computer monitors

Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.2 out of 10, Wonderful, (41 reviews)
"House had everything we needed, and was very well organized! Would definitely recommend!"
United States
Tim W.
The price is HK$1,509
HK$3,927 total
includes taxes & fees
31 May - 1 Jun
Charming open 4bd and screen-in porch! Sleeps 10!
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

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4/10 Poor
"Check in process was very difficult. Staff put down the fact we went thru hotels.com, didn't have both rooms that we reserved, they had overbooked hotel, and had no voice but to valet park , couldn't find our car . I will say staff in pub after game very nice "
Laura 1-night trip
Posted less than an hour ago
Hyatt Regency St. Louis at The Arch

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sky Zone Indoor Trampoline Park - St. Louis, 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?

Aurora Adobe in St. Louis Tremendous 3Bedroom House with AC: This holiday home rental outside of Chesterfield is located next to a golf course, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Choose from 4 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 Missouri River and Sophia M. Sachs Butterfly House 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.