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Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

White House at Grand Central

White House at Grand Central
4.0 star property
Grand Center
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
$120 nightly
The price is $140
Jan 19 - Jan 20, 2026
Total with taxes and fees
White House at Grand Central

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
10.0 out of 10, Exceptional, (4)
"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!"
United States
Zach L.
$89 nightly
The price is $91
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Top of Geyer apartment

Top of Geyer apartment
Soulard
9.8 out of 10, Exceptional, (43)
"Convenient location "
United States
julie s.
$189 nightly
The price is $189
Dec 24 - Dec 25
Total with taxes and fees
Top of Geyer apartment

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, (138)
"Great little place and location was close to our event."
United States
RL T.
$136 nightly
The price is $159
Dec 28 - Dec 29
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!

Lake Aspen Overlook by Innsbrook Vacations!

Lake Aspen Overlook by Innsbrook Vacations!
Innsbrook
9.8 out of 10, Exceptional, (23)
"Everything was extremely clean. We couldn’t have asked for a more quiet and relaxing stay. "
United States
Brian L.
$215 nightly
The price is $221
Dec 24 - Dec 25
Total with taxes and fees
Lake Aspen Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!
Innsbrook
9.6 out of 10, Exceptional, (18)
"Great location and property within close distance of all Innsbrook has to offer. Would stay again. "
United States
Kristina U.
$215 nightly
The price is $221
Dec 24 - Dec 25
Total with taxes and fees
The Harris Overlook by Innsbrook Vacations!

Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
9.8 out of 10, Exceptional, (41)
"Had a good golf day wonderful place to stay "
United States
david c.
$169 nightly
The price is $174
Dec 27 - Dec 28
Total with taxes and fees
Studio Condo on the Water @ Innsbrook

Lake Aspen Hideaway by Innsbrook Vacations!

Lake Aspen Hideaway by Innsbrook Vacations!
Wright City
9.8 out of 10, Exceptional, (21)
"Check-in was easy and property was clean. Great place to stay!"
United States
Casey A.
$214 nightly
The price is $220
Jan 11 - Jan 12, 2026
Total with taxes and fees
Lake Aspen Hideaway by Innsbrook Vacations!

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
2.0 star property
Marine Villa
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
$165 nightly
The price is $179
Jan 12 - Jan 13, 2026
Total with taxes and fees
Stylish South City King 1BR Apt

Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D
Princeton Heights
9.2 out of 10, Wonderful, (19)
"Would stay again, was in a great spot"
United States
Mindy Y.
Elegant Minimalist Gem w/ Private backyard, W/D

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
9.0 out of 10, Wonderful, (9)
"Absolutely beautiful area. Cabin is so cozy"
United States
Aaron
$199 nightly
The price is $221
Dec 30 - Dec 31
Total with taxes and fees
Adorable Augusta Cabin

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (160)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
$141 nightly
The price is $143
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cafe Terrace at TG Park | Fenced Backyard+W/D

Cafe Terrace at TG Park | Fenced Backyard+W/D
2.0 star property
Tower Grove South
9.6 out of 10, Exceptional, (7)
"Much better than staying in a hotel and a block away from my daughter‘s apartment! Local restaurants are great!"
United States
Marguerite B.
Cafe Terrace at TG Park | Fenced Backyard+W/D

Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking
Soulard
9.6 out of 10, Exceptional, (59)
"Enjoyed the vibe of the neighborhood "
United States
Brett
$178 nightly
The price is $192
Jan 12 - Jan 13, 2026
Total with taxes and fees
Cozy Soulard 2BR w/ Free Parking

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)
"Great place for a short get away"
United States
andytrower U.
$174 nightly
The price is $184
Jan 18 - Jan 19, 2026
Total with taxes and fees
Adorable small house - quiet & safe - 2 BR 1 Bath

Pet-Friendly 1BR Apartment

Pet-Friendly 1BR Apartment
Mount Pleasant
8.6 out of 10, Excellent, (10)
"I really enjoyed my stay and the host was very nice and prompt with my questions and concerns however, I would've love to have not had mold in the bathroom on the window ledge and a little more safety regarding the doors. In all the place was very comfortable and yes I would stay here again."
United States
Miltha J.
$142 nightly
The price is $153
Jan 12 - Jan 13, 2026
Total with taxes and fees
Pet-Friendly 1BR Apartment

This apartment is a 2 bedroom(s), 1 bathrooms, located in St. Louis, MO.

This apartment is a 2 bedroom(s), 1 bathrooms, located in St. Louis, MO.
2.0 star property
Downtown West
9.6 out of 10, Exceptional, (7)
"Property met all our needs and management a was prompt and friendly responding to any questions. "
United States
Kevin
$318 nightly
The price is $321
Dec 28 - Dec 29
Total with taxes and fees
This apartment is a 2 bedroom(s), 1 bathrooms, located in St. Louis, MO.

Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck
Soulard
9.8 out of 10, Exceptional, (53)
"Easy check-in, great communication with owner, nice area that is close to restaurants, bars, very clean."
United States
Vickie L.
$189 nightly
The price is $203
Jan 12 - Jan 13, 2026
Total with taxes and fees
Classic Soulard 2BD King Master & Private Deck

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

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
2.0 star property
Ballwin
7.8 out of 10, Good, (23)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
$138 nightly
The price is $138
Dec 25 - Dec 26
Total with taxes and fees
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation 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 vacation.

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 vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Chesterfield Sports Fusion, or you can go with a 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's the top vacation rental that Chesterfield has to offer?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: Visitors like this Chesterfield vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chesterfield?

Choose from 5 Expedia vacation rentals in Chesterfield for a memorable vacation.

What can I see and do in Chesterfield?

Family-friendly attractions include Chesterfield Sports Fusion and Sky Zone Indoor Trampoline Park - St. Louis, 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 vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can book for several days or more in Chesterfield. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.