Holiday houses in Chesterfield

4.91 out of 5 average rating, 408 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, 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 St. Louis

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.

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, 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.

4.97 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.

4.94 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.

4.96 out of 5 average rating, 263 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.

4.9 out of 5 average rating, 626 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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Other great holiday rentals in Chesterfield

4.96 out of 5 average rating, 494 reviews

Home in Dittmer

Honeymoon Suite at Camp Skullbone In The Woods

ChristinaRating, 5 stars3 weeks ago

We stayed here for a mini honeymoon to destress in private. It is very peaceful and private at this beautiful cabin in a wooded area. The road up the hill is narrow, so bring a good driver in good weather. There were very thorough instructions to get to this cute but tucked away location. Inside the cabin are gorgeous floor to ceiling windows that allow a peaceful view of the trees. The furnishings are cute, clean, and thoughtful. The bed is comfortable, the bathroom is spacious, and the kitchenette has everything a couple needs for a few nights away. The TV has Internet and streaming apps. Outside, the wooden porch has a grill, fire pit, and a clean hot tub. There are thoughtfully provided curtains to allow the tub privacy from the (barely used) road. Overall this was a lovely stay and we'd love to return!

4.94 out of 5 average rating, 1,094 reviews

Home in St. Louis

ArtBnB: Enjoy the Curated Comforts of Home

Mae ORating, 5 stars2 weeks ago

This place was beautiful! Perfect especially if you're a fan of fun fungi. The beds a little squeaky when you make any movement at all, but it wasn't too bad! Everything is nicely labeled, but I couldnt tell if there was a deck light somewhere or not. Currently, theres construction happening behind the house that started at like 8am, so just be prepared on that front!

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 stars1 week 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.

4.96 out of 5 average rating, 260 reviews

Tiny home in Pacific

Route 66 Railroad Shanty, a cozy artsy small space

AmandaRating, 5 stars4 days ago

Magical place and such a cute friendly town! All the creative touches throughout the tiny but perfectly appointed house were such a cool atmosphere and the train sounds by the house added another layer of whimsy. Thank you for being a wonderful welcoming spot on the road west!!

5 out of 5 average rating, 16 reviews

Home in Augusta

"The Villa" at Villa Augusta in MO wine country

MichelleRating, 5 stars3 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 stars4 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!