Holiday houses in Chesterfield

4.91 out of 5 average rating, 408 reviews

Home in Bevo Mill

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, 617 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!

Superhost

Home in Dutchtown

4.92 out of 5 average rating, 234 reviews

Private Oasis w/hot tub

Wonderfully renovated 2 bedroom brick bungalow in highly desirable South city location. This home sits on a double lot, which has been completely private, featuring exterior shower with hot and cold, oversized hot tub, stamped concrete, gas fire pit, barbecue pit, and plenty of seating for up to 6 guests. Inside you’ll find home has been completely gut rehabbed featuring exposed brick walls, updated kitchen w/ center island. Two large bedrooms w/ king size beds, all new furnishings throughout.

Apartment in Southwest Garden

4.93 out of 5 average rating, 258 reviews

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, 344 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.

4.95 out of 5 average rating, 104 reviews

Cozy Mid-Century Modern Townhome

This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

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, 113 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.

Apartment in St. Louis Hills

4.84 out of 5 average rating, 281 reviews

Impeccable 1-Bedroom Apartment with Street Parking

Beautiful unit in St.Louis Hills. The apartment is spacious, when you walk in the living room opens up to the dining room and kitchen. The unit is beautifully furnished and has a modern style with all the amenities you could ask for. The building is centrally located, Francis Park is within walking distance. Downtown is about a 10/15 minute drive. Food places in area include Salt and Smoke, Donut Drive In, Mom's Deli, Legrands, Rockwell Beer Garden in Francis park and much more.

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Other great holiday rentals in Chesterfield

4.99 out of 5 average rating, 143 reviews

Guesthouse in Soulard

The PS Carriage House: Spa Tub + Walk Everywhere!

AnnaRating, 5 stars1 week ago

I would definitely stay here again! It was very clean and in a safer neighborhood than most in St. Louis. Katie and Tyler were extremely friendly and helpful. It’s a beautiful guest home and worth the price! I felt safe staying here and it was quiet and peaceful-easy place to relax at. I will be recommending friends and family to stay here as well. Thanks again, Anna & Jordan.

Superhost

4.83 out of 5 average rating, 6 reviews

Luxurious couples retreat just steps from Historic

NiaRating, 5 stars1 week ago

beautiful home. everything was clean and well cared for and had the most beautiful spa

4.94 out of 5 average rating, 86 reviews

Home in Valley Park

Welcome home! Private and tranquil bungalow

LindaRating, 5 stars6 days ago

Elizabeth's place is our favorite to stay at in the St. Louis area. It is very convenient with easy access to 141 and interstate 44.

5 out of 5 average rating, 93 reviews

Home in Ballwin

Pet & Child Friendly*Great Location*Ideal 4 Groups

FaithRating, 5 stars1 week 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.

5 out of 5 average rating, 16 reviews

Home in Augusta

"The Villa" at Villa Augusta in MO wine country

MichelleRating, 5 stars2 days ago

The Villa was lovely for our 2 night stay. The apartment was very clean and the cute decor was a fun touch. Beds were comfortable, bathroom well stocked with extras. And of course I can't skip mentioning the outdoor pool/spa space, which was the icing on the cake. The hosts live on the property and were around, but stayed out of the way and gave us plenty of space. Many wineries are just a few miles away. This is a great space for a few friends or couples to stay.

Guest suite in Weldon Spring

4.93 out of 5 average rating, 45 reviews

Wanderlust

TracyRating, 5 stars3 days ago

Wendy was an excellent host. The lodging was cute and cozy and had all the essentials. She was responsive and helpful whenever I messaged her, but provided us with the utmost privacy while we were there. She checked in several times to make sure we had everything we needed and were comfortable. This lodging had all the essentials and was located in a nice, safe, and quiet neighborhood. I would definitely recommend this airbnb as it was not only affordable but in an excellent location and proximity to the vineyards and any other fun attractions you might want to do. Thanks Wendy!