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Top Holiday Rentals in Chesterfield

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. "
White House at Grand Central

Landing Downtown St. Louis

4.0 star property
7.6 out of 10, Good, (10)
"It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot."
Landing Downtown St. Louis

Beautiful, Rehabbed Unit in Shaw Community 4228a

7.2 out of 10, Good, (15)
"Very clean Spacious Beds were comfy "
The price is £201
includes taxes & fees
4 Aug - 5 Aug
Beautiful, Rehabbed Unit in Shaw Community 4228a

St Louis Townhome-Perfect for Groups!

8.0 out of 10, Very good, (49)
"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 £184
includes taxes & fees
10 Aug - 11 Aug
St Louis Townhome-Perfect for Groups!

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

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!

9.8 out of 10, Exceptional, (117)
"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 £127
includes taxes & fees
10 Aug - 11 Aug
Centrally located in the Tower Grove East neighborhood!

StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

10.0 out of 10, Exceptional, (273)
"Great place, great location"
The price is £123
includes taxes & fees
6 Aug - 7 Aug
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

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 £310
includes taxes & fees
7 Aug - 8 Aug
Stunning 1890's Home - Sleeps 8!

Stylish City Reno Retreat!

7.2 out of 10, Good, (7)
Stylish City Reno Retreat!

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (16)
"Walking distance to several bars and restaurants, the market, and we got front row parking. "
The price is £124
includes taxes & fees
11 Aug - 12 Aug
Cozy Soulard Getaway

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 £145
includes taxes & fees
4 Aug - 5 Aug
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

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!

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!

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

10.0 out of 10, Exceptional, (3)
"We had a nice stay in the area, and we were looking for a reasonably priced lodging for the whole family. There are a couple inflatable mattresses included in case additional beds are required. The full kitchen was appreciated, as was the comfortable couch. Solid proximity to other businesses and towns. The property is a little tricky to spot from afar off the side of the road, but it's easy to see once you're near it (Google maps is helpful). Overall, a good stay & I would stay here again!"
The price is £70
includes taxes & fees
6 Aug - 7 Aug
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Cozy 2BR | Near Downtown | St. Louis

8.6 out of 10, Excellent, (4)
"This was the absolute perfect little historic place! The beds were ultra comfortable. It was short ride to everything we wanted to do. My kids and I enjoyed our entire stay. "
Cozy 2BR | Near Downtown | St. Louis

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

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (23)
"Great spot! We would stay again."
The price is £159
includes taxes & fees
4 Aug - 5 Aug
Convenience 2 Bedroom House to Explore All of St Louis

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

2.0 star property
7.8 out of 10, Good, (22)
"The property was quiet and as expected. They were incredibly responsive and helpful with everything. "
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit

10.0 out of 10, Exceptional, (25)
"Great time and property! We enjoyed fishing on the private dock, taking the kayaks out that were provided, having a fire in the fire pit, taking a few hikes as well as having a ping pong tournament. Wonderful stay! "
Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit
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

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.