Photo by Michelle E

Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Chesterfield

Landing Downtown St. Louis
Property amenity

Landing Downtown St. Louis

4.0 star property
8.0 out of 10, Very good, (11)
"Good place!"
Landing Downtown St. Louis
White House at Grand Central
Prepare meals in this well-equipped kitchen with a stove, refrigerator, and microwave.

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (114)
"It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay. "
The price is HK$747
HK$1,378 total
includes taxes & fees
12 Aug - 13 Aug
White House at Grand Central
St. Charles 1860's Gem - Sleeps 6!
Enjoy cooking in this well-equipped kitchen with an oven, dishwasher, and sink.

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (112)
"Great time and nice and quiet :) "
The price is HK$981
HK$1,962 total
includes taxes & fees
10 Aug - 11 Aug
St. Charles 1860's Gem - Sleeps 6!
Beautiful, Rehabbed Unit in Shaw Community 4228a
Enjoy cooking in this well-lit kitchen with stainless steel appliances and white cabinetry.

Beautiful, Rehabbed Unit in Shaw Community 4228a

7.2 out of 10, Good, (15)
"Very clean Spacious Beds were comfy "
The price is HK$353
HK$2,061 total
includes taxes & fees
12 Aug - 13 Aug
Beautiful, Rehabbed Unit in Shaw Community 4228a
Landing at Ballpark Heights - 1 Bedroom in Down...
Terrace/patio

Landing at Ballpark Heights - 1 Bedroom in Down...

9.0 out of 10, Wonderful, (24)
"Nice clean space to stay. Close to all amenities "
Landing at Ballpark Heights - 1 Bedroom in Down...
St Louis Townhome-Perfect for Groups!
Enjoy cooking in this well-lit kitchen with a central island, stainless steel appliances, and large windows offering a view of the outdoors.

St Louis Townhome-Perfect for Groups!

8.0 out of 10, Very good, (50)
"The property was nice and well laid out and the location near Forest Park was great! Checking in was really easy, which isn't always the case with short term rentals."
The price is HK$463
HK$1,876 total
includes taxes & fees
17 Aug - 18 Aug
St Louis Townhome-Perfect for Groups!
Charming 1-bedroom home in the heart of The Hill!
Microwave, oven, stovetop, paper towels

Charming 1-bedroom home in the heart of The Hill!

10.0 out of 10, Exceptional, (5)
The price is HK$903
HK$1,374 total
includes taxes & fees
15 Aug - 16 Aug
Charming 1-bedroom home in the heart of The Hill!
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Enjoy a spacious living area with a dining table and chairs, a kitchen with modern appliances, and large windows.

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

9.6 out of 10, Exceptional, (44)
"This place is the cutest little bungalow. Beautiful and clean. I couldn't have asked for a better place to stay. "
The price is HK$1,053
HK$2,552 total
includes taxes & fees
8 Aug - 9 Aug
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
The St. Charles Guest House, lovely historic home, fun for families and groups
Outdoor dining area with tables and chairs, surrounded by trees and a brick building.

The St. Charles Guest House, lovely historic home, fun for families and groups

10.0 out of 10, Exceptional, (130)
"We very much enjoyed the property and location. "
The St. Charles Guest House, lovely historic home, fun for families and groups
Entire Dogtown House near Zoo, Forest Park and Wash U
Stunning two-story home with a central entrance, white door, and a small porch area.

Entire Dogtown House near Zoo, Forest Park and Wash U

10.0 out of 10, Exceptional, (208)
"Very nice and comfy home. Enjoyed our time and the hosts were great. "
Entire Dogtown House near Zoo, Forest Park and Wash U
Modern House with Terrace Near Forest Park
Relax in the serene backyard patio, surrounded by lush plants and a tree with vibrant foliage.

Modern House with Terrace Near Forest Park

9.0 out of 10, Wonderful, (11)
"This house had a lot of great wuakotirs"
Modern House with Terrace Near Forest Park
Centrally located in the Tower Grove East neighborhood!
Relax in a cozy retreat with a comfortable seating area, plush sofa, and vintage charm.

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (122)
"Thoroughly enjoyed staying here. My sister and I were in town for an event and staying here made it even more fun!"
The price is HK$558
HK$1,288 total
includes taxes & fees
10 Aug - 11 Aug
Centrally located in the Tower Grove East neighborhood!
Stunning 1890's Home - Sleeps 8!
Enjoy cooking in this well-lit kitchen with appliances and a spacious island.

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (68)
"Adorable place with plenty of room for our group of five ladies. Walkable to Main St to the shops and restaurants. All the beds were comfortable, nice to have two full bathrooms and all the amenities you could want. "
The price is HK$1,531
HK$3,153 total
includes taxes & fees
11 Aug - 12 Aug
Stunning 1890's Home - Sleeps 8!
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Fully equipped kitchen with two sinks, coffee maker, and ample counter space.

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

8.6 out of 10, Excellent, (12)
"Home was clean and conveniently located to our event. "
The price is HK$934
HK$1,484 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Stylish City Reno Retreat!
Enjoy cooking in this well-equipped kitchen with appliances and a dining area.

Stylish City Reno Retreat!

7.2 out of 10, Good, (7)
Stylish City Reno Retreat!
Large Executive 1st Floor Apartment with Chefs Kitchen!
Relax in the spacious living room with a comfortable sectional sofa, exposed brick walls, and a stylish chandelier.

Large Executive 1st Floor Apartment with Chefs Kitchen!

9.0 out of 10, Wonderful, (15)
"This place is beautiful! Comfortable bed, big kitchen. Nice living room area. Quiet and safe. We liked it a lot. "
Large Executive 1st Floor Apartment with Chefs Kitchen!
Cozy Soulard Getaway
Enjoy an outdoor space with a flat table and metal railing, surrounded by a brick wall and staircase.

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (17)
"Walking distance to several bars and restaurants, the market, and we got front row parking. "
The price is HK$565
HK$1,264 total
includes taxes & fees
13 Aug - 14 Aug
Cozy Soulard Getaway
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly
Enjoy cooking in this fully equipped kitchen with stainless steel appliances, white cabinetry, and a coffee maker and kettle.

Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly

9.6 out of 10, Exceptional, (73)
"We had a great stay "
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly
Overlook Main St. in this 2 Bedroom Owners Suite!
Enjoy cooking in this well-lit kitchen with a dishwasher and stainless steel refrigerator.

Overlook Main St. in this 2 Bedroom Owners Suite!

4.0 star property
9.4 out of 10, Exceptional, (31)
"Perfect place for a visit to St Charles! Hope to return and stay here again!"
Overlook Main St. in this 2 Bedroom Owners Suite!
Cowboy Cabin, come sit under the trees
Relax on the porch with a round table and two chairs, surrounded by lush greenery and a natural wooded view.

Cowboy Cabin, come sit under the trees

10.0 out of 10, Exceptional, (199)
"This was our second trip, this time with the kids! It was a refreshing weekend with lots of quality time, beautiful weather and lovely scenery! "
Cowboy Cabin, come sit under the trees
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

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

10/10 Excellent
"Very clean and friendly staff. Breakfast was excellent"
Michelle 1-night trip
Posted 2 days ago
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

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?

Convenience 2 Bedroom House to Explore All of St Louis: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chesterfield?

Choose from 13 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 Chesterfield Sports Fusion, 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.