Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Chesterfield

Fridge, microwave, oven, coffee/tea maker
Stylish South City King 1BR Apt

Stylish South City King 1BR Apt

2.0 star property
Marine Villa
10.0 out of 10, Exceptional, (8)
"Very clean! No problems!"
United States
Mary
$165 nightly
The price is $179
Nov 9 - Nov 10
Total with taxes and fees
Stylish South City King 1BR Apt
Outdoor dining
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
9.4 out of 10, Exceptional, (6)
"We rented this property because it was convenient to our son's home, which is directly across Tower Grove Park. The one bedroom layout was perfect, and the lodging was exceptionally clean. I highly recommend this VRBO."
United States
Bob K.
$144 nightly
The price is $165
Nov 11 - Nov 12
Total with taxes and fees
Cafe Terrace at TG Park | Fenced Backyard+W/D
Fridge, microwave, oven, stovetop
Stylish South City 2BR w/ Garage & Blazing Wi-fi

Stylish South City 2BR w/ Garage & Blazing Wi-fi

Dutchtown
9.6 out of 10, Exceptional, (48)
"We loved our stay here. Perfect for our family of 5, good location, easy access and very clean. Would definitely stay here again!"
United States
Joel J.
$193 nightly
The price is $207
Nov 9 - Nov 10
Total with taxes and fees
Stylish South City 2BR w/ Garage & Blazing Wi-fi
Comfort Apartment | 1 bedroom, individually decorated, individually furnished, desk
White House at Grand Central

White House at Grand Central

4.0 star property
Grand Center
8.4 out of 10, Very Good, (122)
"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. "
United States
Sharon
$133 nightly
The price is $155
Nov 12 - Nov 13
Total with taxes and fees
White House at Grand Central
Fridge, microwave, oven, stovetop
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, (154)
"Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing "
United States
Lindsay
$132 nightly
The price is $134
Nov 10 - Nov 11
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Fridge, microwave, oven, stovetop
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)
"Really nice for a small family. "
United States
Melissa M.
$188 nightly
The price is $199
Nov 16 - Nov 17
Total with taxes and fees
Adorable small house - quiet & safe - 2 BR 1 Bath
Interior
Top of Geyer apartment

Top of Geyer apartment

Soulard
9.8 out of 10, Exceptional, (40)
"This place was great! I loved the location and Bonnie recommended a bunch of awesome places to eat within walking distance. We will definitely be booking another stay in the future!"
United States
Alena G.
$192 nightly
The price is $192
Nov 10 - Nov 11
Total with taxes and fees
Top of Geyer apartment
Fridge, microwave, oven, stovetop
Elegant Minimalist Gem w/ Private backyard, W/D

Elegant Minimalist Gem w/ Private backyard, W/D

Princeton Heights
9.2 out of 10, Wonderful, (16)
"This was our second stay and everything was great! The place has everything you would have back at home.We walked to local restaurants and enjoyed looking at the decorations on the neighborhood homes. "
United States
- P.
$147 nightly
The price is $169
Nov 11 - Nov 12
Total with taxes and fees
Elegant Minimalist Gem w/ Private backyard, W/D
Dining
Charming Tower Grove Flat-Steps to T.G Park+Grand

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

Tower Grove East
9.8 out of 10, Exceptional, (11)
"My partner and I had a fantastic stay! The unit was very clean and organized. The location is phenomenal for getting around the area and the parking spot is a total plus! The host did a great job communicated with us and helping with anything that came up. Overall we could not have asked for a better stay and would recommend this unit to everyone!"
United States
Caden S.
$139 nightly
The price is $159
Nov 11 - Nov 12
Total with taxes and fees
Charming Tower Grove Flat-Steps to T.G Park+Grand
Fridge, microwave, oven, stovetop
Classy Midtown 3BR, King Master

Classy Midtown 3BR, King Master

The Gate
10.0 out of 10, Exceptional, (59)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
$193 nightly
The price is $207
Nov 11 - Nov 12
Total with taxes and fees
Classy Midtown 3BR, King Master
Bar (on property)
Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook

Wright City
9.8 out of 10, Exceptional, (39)
"Had a good golf day wonderful place to stay "
United States
david c.
$177 nightly
The price is $183
Nov 9 - Nov 10
Total with taxes and fees
Studio Condo on the Water @ Innsbrook
Smart TV, fireplace, books
Aspen Vista by Innsbrook Vacations!

Aspen Vista by Innsbrook Vacations!

Innsbrook
9.6 out of 10, Exceptional, (11)
"Our family had a great stay. We were able to enjoy the pool and playground. The house had plenty for all ages to enjoy. "
United States
Janice
$517 nightly
The price is $532
Nov 25 - Nov 26
Total with taxes and fees
Aspen Vista by Innsbrook Vacations!
Interior
Cozy Soulard 2BR w/ Free Parking

Cozy Soulard 2BR w/ Free Parking

Soulard
9.6 out of 10, Exceptional, (55)
"Wonderful location with wonderful hosts-super easy to communicate with. Highly recommended!!"
United States
Matthew W.
$178 nightly
The price is $192
Nov 11 - Nov 12
Total with taxes and fees
Cozy Soulard 2BR w/ Free Parking
Fridge, microwave, oven, stovetop
Classic Soulard 2BD King Master & Private Deck

Classic Soulard 2BD King Master & Private Deck

Soulard
9.8 out of 10, Exceptional, (51)
"Unequivocally recommend!"
United States
Lisa M.
$189 nightly
The price is $203
Nov 11 - Nov 12
Total with taxes and fees
Classic Soulard 2BD King Master & Private Deck
2 bedrooms, iron/ironing board, travel crib, free WiFi
Spacious & Centrally Located Apt (Sleeps 8)

Spacious & Centrally Located Apt (Sleeps 8)

The Gate
9.8 out of 10, Exceptional, (18)
"It was very clean. Owner was very pleasant and polite. Kids enjoyed their stay. Wonderful experience! Definitely will stay again."
United States
Angela B.
$190 nightly
The price is $204
Nov 9 - Nov 10
Total with taxes and fees
Spacious & Centrally Located Apt (Sleeps 8)
Fridge, microwave, oven, stovetop
Innsbrook lakefront A-Frame, kayaking, paddle boarding and more

Innsbrook lakefront A-Frame, kayaking, paddle boarding and more

Innsbrook
10.0 out of 10, Exceptional, (27)
"Great place in the woods on a lake"
United States
Jared H.
$413 nightly
The price is $429
Nov 9 - Nov 10
Total with taxes and fees
Innsbrook lakefront A-Frame, kayaking, paddle boarding and more
1 bedroom, iron/ironing board, travel crib, free WiFi
Comfy King 1BR Heart of Soulard

Comfy King 1BR Heart of Soulard

Soulard
10.0 out of 10, Exceptional, (13)
"Great property with a host that always quickly responded to our questions/requests. If you want to experience the best of the Soulard neighborhood, this property is perfectly located with bars, the market and plenty of coffee shops in easy walking distance."
United States
Mark G.
$175 nightly
The price is $189
Nov 11 - Nov 12
Total with taxes and fees
Comfy King 1BR Heart of Soulard
Interior
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, (132)
"Great stay, comfortable furnishings, quiet street. "
United States
Tracy C.
$143 nightly
The price is $168
Nov 10 - Nov 11
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!
Smart TV, fireplace
Turrach Ridge Escape by Innsbrook Vacations!

Turrach Ridge Escape by Innsbrook Vacations!

Innsbrook
10.0 out of 10, Exceptional, (40)
"Fantastic property. Beautiful and clean. Love this little community!"
United States
Eric B.
$451 nightly
The price is $462
Nov 25 - Nov 26
Total with taxes and fees
Turrach Ridge Escape by Innsbrook Vacations!
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, (36)
"Great spot! We would stay again."
United States
Heather P.
$247 nightly
The price is $265
Nov 9 - Nov 10
Total with taxes and fees
Convenience 2 Bedroom House to Explore All of St Louis
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

Forest Park Hotel by MDR

Forest Park Hotel by MDR

10/10 Excellent
"I arrived at almost 4 am after a long day at the hospital—my mom had surgery, & I just needed a few hours of real rest before heading back. Hotels.com and the front desk staff made it super easy to check in way before the normal 3 p.m. time, no hassle at all. The room was spotless, bed was so comfortable, and it honestly felt like heaven after trying to sleep upright in those awful hospital chairs. Exactly what I needed when I needed it."
Sierra 1-night trip
Posted 9 hours ago
Forest Park Hotel by MDR

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 $134 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sky Zone Indoor Trampoline Park - St. Louis, 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?

Madison House 2 -Walk to Main St: Visitors like this Chesterfield vacation home rental. It is equipped with an arcade game room, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chesterfield?

Choose from 3 Expedia vacation rentals in Chesterfield for a memorable vacation.

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 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.