Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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Top guest favourite

Tiny home in Pacific

4.96 out of 5 average rating, 265 reviews

Route 66 Railroad Shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

Top guest favourite

Home in Saint Charles

4.98 out of 5 average rating, 621 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!

Top guest favourite

Cabin in Saint Charles

4.98 out of 5 average rating, 350 reviews

Camp Mill Pond: Historic Cabin Near Main Street

*St. Louis Magazine A-List Winner!* ***PRESS: DESIGN STL, STL MAG, AND FOX2NEWS*** Camp Mill Pond is a throwback to the slow and easy rhythm of hot summer days. This circa 1835 cabin offers easy access to our historic area, including Main Street, Katy Trail for biking, and Frenchtown, without sacrificing modern comforts! This 180-year-old historic cabin sits on a beautiful lot, shared with our 1865 three-story home and a two-story carriage house. Ask about renting bikes and a golf cart!

Top guest favourite

Flat in St. Louis

4.94 out of 5 average rating, 264 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

Top guest favourite

Flat in St. Louis

4.99 out of 5 average rating, 162 reviews

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Top guest favourite

Home in Villa Ridge

4.93 out of 5 average rating, 116 reviews

Serenity Valley (No Cleaning Fee)

Discover serenity in this Studio 675 sq ft Airbnb amidst nature. Cozy space with 1 queen bed, optional inflatable queen bed for up to 4 guests. Amenities include WIFI, washer/dryer, full kitchen, DirecTV with parental controls. Vintage clawfoot tub, panoramic woods view. Family-friendly with a pack and play. Owners next door for quick resolutions. Relax on the deck. Just 60 mins from downtown STL, 15 mins from Washington, and 20 mins from Missouri wine country. Your tranquil escape awaits!

Top guest favourite

Cottage in Saint Charles

4.97 out of 5 average rating, 320 reviews

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!

Guest favourite

Home in Saint Charles

4.95 out of 5 average rating, 311 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.

Superhost

Flat in St. Louis Hills

4.84 out of 5 average rating, 287 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.

Guest favourite

Home in Saint Charles

4.96 out of 5 average rating, 266 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.

Guest favourite

Tiny home in Pacific

4.9 out of 5 average rating, 633 reviews

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

Guest favourite

Guest suite in Dardenne Prairie

4.89 out of 5 average rating, 274 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh