
Apartment holiday rentals in Chesterfield
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Top-rated apartment rentals in Chesterfield
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Historic Elegance in the Heart of St. Louis City!
Classical elegance with a modern twist. This apartment is nestled in the heart of St. Louis City. Walking distance to Anheuser-Busch, amazing restaurants and bars. Very short Uber ride to the historical Cherokee Antique Row shopping district and only 5-10 min ride to downtown! Free parking in front makes arriving easy. We live in the area and can respond/resolve to any questions or concerns you may have. Notice: Laundry is down slightly steep stairs to basement, please consider before booking!

3-bdrm apt near Pageant, Wash U, Forest Park, Loop
Three bdrm, top floor apt. with private entrance in our home. Roomy, comfy, well-furnished with everything you need. Walk to Pageant, Delmar Hall, WashU, Blueberry Hill, Salt&Smoke, MagicMiniGolf. CVS, grocery, restaurants and shops on the Delmar Loop. Or stroll our leafy streets to Forest Park, built 1904 for a World’s Fair, now a first-class museum, zoo, golf course, boat rental. Easy access via metro train or Uber/Lyft to airport, baseball, hockey, live music clubs, City Museum, the Arch.

Lofty fun for all at King of the Hill
Welcome to the "King of the Hill"—the ultimate "game room," and "fan-cave" for families, couples, and solo travelers, in the heart of St. Louis' "Little Italy": The Hill! The open, industrial-chic loft space has exposed brick, all new kitchen appliances, polished concrete counters, slate bathroom, spacious deck, comfy queen master, and twin-over-full bunk bed. The unit was recently updated with a central HVAC unit. Fun includes Pac-man, Kid Friendly Darts, Atari, Air-hockey & board games!

Centrally Located Mid-Century Modern Retreat
Make yourself at home in the thoughtfully restored historic apartment located in the heart of St. Louis City which boasts both historic and modern elements. You will be minutes away from all major highways, eateries, attractions, and entertainment the city has to offer. "Come stay at this mid-century modern retreat, you'll be central to everything St. Louis has to offer and I'm committed to making your stay the best and safest possible using an enhanced cleaning process! " - Sean, Your Host

Stunning Modern Apt| King-bed 5 min CreveCoeurLake
Experience luxury and style in our St. Louis home. This second-floor residence features 2 modern bedrooms, a cozy living room, a fully equipped kitchen, a stylish bathroom, and a dedicated workspace with high-speed WiFi- blending comfort and elegance. Located in a secure Maryland Heights community, just minutes from Creve Coeur Lake, Westport Plaza, Hollywood Casino & Amphitheatre, and historic St. Charles. With plush bedding, premium amenities, and ample parking, we promise a seamless stay!

Historic Victorian comfort Great safe nghbhd
First, check out all 4 of our private 5 Star listings that creatively combines the old with the new. If one is unavailable, check the others by going to “My Profile” and scrolling down until you see all 4. This Historic building; built in 1896 has changed missions through the years; From church, to merc. Trade, to grocery store; quite the history have graced these walls. You’ll love our safe, Southwest Gardens area; next to the famous “Hill” offers unmatched restaurant, shops, bakeries

Charming Pop Lucks Guest Suite in Old St. Charles
Welcome to Pop Luck's Guest Suite! This adorable gem represents everything you love about Old St. Charles. This cozy suite is just steps away from the heart of Main Street, restaurants, and all the action St. Charles has to offer. Pop Luck's is a charming one-bedroom, with an open and airy living room and kitchen. It has natural light and high ceilings throughout. It's farmhouse cottage decor makes for a relaxing place to rest. Also, check out our sister suite The Ella Rose, right next door.

Luxurious Downtown Loft Steps From City Museum
You and your group will adore this stunning & spacious downtown 4th floor loft located right on the popular Washington Avenue in St. Louis! You will be in a prime location and can walk to so many restaurants, cafes, shops, bars, and even attractions like The City Museum and Union Station! Cozy up on the plush couch, turn on the gas fireplace, and enjoy a gorgeous sunset view right from the living room! With a spa tub, luxury bedding/towels/bath robes, and furnishings…you won’t want to leave!

This Must Be The Place | Soulard
This MUST be the place- the perfect combination of historic and modern luxury! The original hardwood floors, exposed brick and tiled ceiling pair wonderfully with the quartz-waterfall island, LED lighting, soft-close cabinetry and all the other contemporary updates. From your front door you can walk to Dukes Sports Bar, 1860s Saloon for live music, Molly's Night Club, Bogarts BBQ, and everything else Soulard offers. Take a <5min Uber downtown to Cardinals, Blues and STL City soccer games!

2026 Sale! Charming Kirkwood (2) Bedroom
Welcome to this cozy home-away-from-home, designed with the Airbnb guest in mind! Minutes from downtown Kirkwood and 20 minutes from downtown STL it is perfect for those traveling for work or fun! Guests are provided internet, hotel linens, & laundry access. Settle in & enjoy cooking in the kitchen, relaxing in the living room, and resting in your hotel-inspired bedrooms. This listing was converted from a shared apartment to a full unit in August 2024. Prior reviews are for one bedroom.

Bella Nido
Fully renovated and stylish studio apartment centrally located in the heart of the historic Hill neighborhood in the City of St. Louis. Walk out the front door and explore the coffee shops, Italian markets, and restaurants that this wonderful neighborhood has to offer. The Hill neighborhood is located within a short drive to most St. Louis area attractions including, The Arch, Cardinal Baseball, Blues Hockey, City Soccer, St. Louis Zoo, Forest Park, Botanical Gardens, Museums, and more!

1st Flr -Tower Grove Artsy Apt
Artsy PRIVATE 1st-floor apartment in S. Grand/Tower Grove. GREAT LOCATION! This flat is part of a two-family building. Both flats are Airbnb rentals. Fully-loaded kitchen, 2 bedrooms, private garage parking, use of beautiful back yard. Living Room has a comfy queen-size pull-out bed. Less than 1 block off S. Grand with lots of cafes & shops. 3 blocks from Tower Grove Park. LGBTQ friendly! If booked in advance, both flats in this house can be booked at the same time.
Popular amenities for Chesterfield apartment rentals
Weekly apartment rentals

2026 Sale! Cozy Kirkwood (2) Bedroom

Pink Cloud Retreat | Chic 1BR Near Tower Grove

Inviting Mediterranean Retreat

NEW Historic Bevo Mill I 2bd + Cozy Retreat

Lovely 1 bedroom 1 bath apartment close to town.

Historic Soulard King 2BR Apt w/ Private Deck

Walk to Busch and Free Parking Downtown

Cozy, spacious lower level apart near airport/hwys
Private apartment rentals

Gorgeous condo in HEART of STL! Gourmet kitchen✨

Flower Shop Retreat

Your home away from home.

Modern Chic apartment in Tower Grove/CWE

Brick & Bed - Amazing Riverfront & Arch Views

Luxury 2bd/Free parking/Nr Airport/Bkyrd firepit

Lavender Luxe Retreat w/ Firepit near The Grove

Forsyth Prime luxury apartment 2F
Apartment rentals with a hot tub

Stylish Downtown Penthouse Views ABODEbucks

Beatles Room in Historic Hostel with Hot Tub

English Tea Room in Historic Hostel with Hot Tub

African Beats Room in Historic Hostel with Hot Tub

Resort Style Burb Suite 20mins/DT/Extended Stays

Stunning Centrally Apartment w/ Kingbed |Firepit

Modern 1BR w/Balcony Near Forest Park, WashU &SLU

2bd/2ba, private balcony downtown STL
Quick stats about flat rentals in Chesterfield

Total holiday rentals
Explore 10 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
10 of Chesterfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.5 Average rating
Chesterfield stays receive an average rating of 4.5 out of 5 from guests
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- Busch Stadium
- Central West End
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- St. Louis Aquarium at Union Station
- City Museum
- Missouri Botanical Garden
- Hidden Valley Ski Resort
- Gateway Arch National Park
- The Dome at America's Center
- Meramec State Park
- Castlewood State Park
- Gateway Arch
- Cathedral Basilica of Saint Louis
- Washington University in St Louis
- Forest Park
- Saint Louis Science Center
- Saint Louis University
- Stifel Theatre
- Missouri History Museum
- Fabulous Fox
- Laumeier Sculpture Park
- Soulard Farmers Market




