Vacation rentals in Chesterfield

4.91 out of 5 average rating, 409 reviews

Home in St. Louis

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

4.92 out of 5 average rating, 144 reviews

Home in Pacific

Pacific Palace, super unique!

The Pacific Palace is unlike any other Airbnb! Located in the heart of downtown Pacific, Missouri - only 2 minutes from Highway 44 and 10 minutes from Purina. This house is an incredible one of a kind treasure with lots of unique features including: outdoor gazebo, fish pond, all original cedar interior design, two second story balconies, two large bat tubs (one located in the main bedroom) and so much more!!! Private parking and a gate for added privacy. Just minutes from Six Flags. Book today

4.98 out of 5 average rating, 618 reviews

301 Guesthouse- Historic Main street-Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

4.93 out of 5 average rating, 258 reviews

Apartment in St. Louis

Historic Victorian, Great neighborhood,2nd Floor

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

Guest suite in Lindenwood Park

4.93 out of 5 average rating, 345 reviews

Home Suite Home

A NEIGHBORHOOD home with a small town vibe; great for work travelers; safe for children; a suite in the BASEMENT of my home; PRIVATE Entry, Bedroom, Full Bath, Family Room and Kitchenette; Yard and Patio are private during your stay; walk to Historic Route 66, restaurants, coffee shops, shopping, churches, parks/playgrounds/trails; 10-20 minutes from Lambert Airport, Downtown STL, historic neighborhoods, and major attractions; minutes to major US Highways. VIEW ALL PHOTOS/READ PHOTO DETAILS.

4.97 out of 5 average rating, 317 reviews

Cottage in Saint Charles

The Rose Cottage -a short walk to Historic Main St

The Cottage has a 2 guest maximum Updated 1 bedroom home a three minute walk from historic Main Street and festivals like Oktoberfest, Christmas Traditions and Festival of the Little Hills, the Lewis and Clark Boat House, Foundry Arts Center, Katy Trail and more! Located 10 minutes from the airport , 2 minutes from Ameristar Casino and Bass Pro Shop. 25 minutes from downtown St. Louis, The Arch, Forest Park, Zoo, Art Museum, History Museum and Busch Stadium-home of Cardinals Baseball!

4.95 out of 5 average rating, 309 reviews

*HotTub* The Jewel on 5th-2br2b-near Historic Main

A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. Can sleep 6.

4.84 out of 5 average rating, 114 reviews

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade

Our freshly updated and furnished house is ready for the family with kids, the adult getaway, and wedding parties from Stone House event venue across the street! Boasting tons of privacy, a huge yard with a playset and games, a fully stocked kitchen with everything you could want for a Thanksgiving dinner, and a large basement with arcade boxes, ping pong, weights, and seating areas. A very safe and secluded location that is close to amazing parks, restaurants, wineries, and shopping.

4.94 out of 5 average rating, 108 reviews

Home in O'Fallon

Beautiful 2 bedroom ranch home

The whole group will enjoy easy access to everything from this centrally located ranch home. This home has everything you will need for a cozy, relaxing stay. Our home is located in the middle of everything such as shopping, entertainment, restaurants, and hospital's. You can also enjoy staying in and cooking your own meals with a full kitchen. If this property isn't available for the dates you are needing I have another property listed under The Ladybug Inn in Wentzville Missouri.

4.96 out of 5 average rating, 264 reviews

Bright & Cozy Shotgun DPX 1 Block from Historic DT

Admire this unique historic home's design with brand new amenities and antique details that give a fresh and charming feel. Built in the 1930's, this half of the duplex has a typical shotgun layout with ten-foot ceilings giving a spacious feel. The front door leads directly to the living room, then into the bedroom, both of which have the original hard wood floors. The back of the house has the kitchen, with exposed brick, a dining area, and a bathroom with a washer and dryer.

4.86 out of 5 average rating, 440 reviews

Home in Soulard

The Soulard Cottage | There Is Only One

Built in 1894, this historic, free-standing Cottage is a staple in Soulard. The Soulard Cottage is steps away from McGurks, Dukes, Mollys and all of Soulard's hottest spots! Not to mention, less than a 8 minute Uber to The Arch, Busch Stadium (Cardinals), Enterprise Center (Blues), the City Museum, The Aquarium and so much more! Here for business? Perfect! Here for a game? Perfect! This cottage will give you a truly unique experience while you explore St. Louis.

4.9 out of 5 average rating, 628 reviews

Tiny home in Pacific

Route 66 Cozy Cottage

* Fast Wifi (Spectrum) * Keypad entry (no keys to keep track of) * Private driveway by the front door for easy access to carry luggage in and out * Huge yard for dogs, kids or even adults to play * Lovely outdoor patio with plenty of comfortable seating and beautiful landscaping * For the kiddos- toys, books, and games (puzzles and games for adults too) * Essentials for your furbabies as well - treats, leashes, food & water bowls, waste bags, towels

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Popular amenities for Chesterfield vacation rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chesterfield

Guest favorite

Apartment in Saint Charles

4.89 out of 5 average rating, 103 reviews

The Historic Bricks on Main

KathyRating, 5 stars2 weeks ago

A very ample, nicely furnished and well appointed apartment. Clean, comfortable and close to happenings in historic St. Charles!

5 out of 5 average rating, 93 reviews

Home in Ballwin

Pet & Child Friendly*Great Location*Ideal 4 Groups

FaithRating, 5 stars2 weeks ago

Exceeded expectations in every way! This beautifully decorated four bedroom, one story home, had everything we needed for an effortless nine day stay. All appliances and TV’s were state of the art, the house was super clean, the beds comfortable, and the kitchen was fully equipped. We’re in our mid seventies and appreciated how accessible everything is in this home. Highly recommend.

Guest favorite

Home in Caseyville

4.97 out of 5 average rating, 59 reviews

Downtown STL view with Free Bottle of wine+brkfst

JuanitaRating, 5 stars1 day ago

Great place! The bed was so comfortable and there was great water pressure in the shower. Now that I got the important stuff out the way, this place is so cute! I came in with my pup and stayed in St. Louis for about a day and a half, and this was perfect for us. It is exactly like the photos and the host were responsive and so kind. I was able to drive into and from STL easy peasy. I would definitely recommend this place!

5 out of 5 average rating, 21 reviews

Home in Wildwood

3 private acres, Koi fish pond, garage parking

AllisonRating, 5 stars4 days ago

Very beautiful house!! We all really enjoyed it, it is just far enough out of the city to feel like you are on a peaceful retreat!

4.98 out of 5 average rating, 65 reviews

Cabin in Pacific

Catch The Dream:; An Immersive Equestrian Escape

MichelleRating, 5 stars2 weeks ago

Lynette’s place really deserved a few nights stay at least but we only stayed for a night. It was easy to find and very clean inside. The bathroom was very clean and renovated as well. We would definitely come back!

Home in Creve Coeur

4.73 out of 5 average rating, 11 reviews

Spacious Creve Coeur Retreat

JeremyRating, 5 stars5 days ago

DJ was freat to work with and always quick to respond to questions I had. The home was a great fit for what we needed for time to relax and hang out in a comfortable space. Thanks so much! We will stay again if back to STL.

Guest favorite

4.97 out of 5 average rating, 33 reviews

Home in St. Charles, MO

ALL-EN Luxury Stays & Rentals LLCRating, 5 stars2 weeks ago

Scott is a great host—friendly, responsive, and easy to communicate with. His place is modern, super clean, and incredibly cozy. You can tell he puts a lot of thought into making guests feel comfortable. Our favorite spot—especially for the kids—was the basement. It was the perfect place for them to play and relax. We had a wonderful stay and would definitely come back again!