
House vacation rentals in Chesterfield
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Top-rated house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

Private Walkout w King Bed & Bath + large livingrm
Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

New: Cozy Cottage Near The Hill
Enjoy full access to this adorable cottage, also known as “The Blue Abode.” It is a small house with a large fenced-in backyard, and 2 off-street parking spaces nestled along the 15-acre Sublette Park in Southwest Gardens, within walking distance to restaurants and shops on The Hill. Freshly updated with modern renovations and stylish furnishings, this cozy pet-friendly home ($100 pet fee) is perfect for a solo traveler and spacious enough for up to 4 guests. Body wash and shampoo dispenser.

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!

A Kirkwood Cottage, Quaint Suburb of St Louis
Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children. Home has steps to entry & is 4th house from railroad tracks that are up on the hill at end of street.Close easy access to all major highways

Dog Friendly! Dogtown Getaway Mins from Zoo
Relax with the whole family in this peaceful 1 bedroom home in the highly desirable Dogtown neighborhood in St.Louis. The home is located just minutes away from the amazing St.Louis Zoo, historic Forest Park and some of the best restaurants in town. Getting around to the other sights in town will be easy with hwy 40 and 44 just minutes away as well! With a giant king bed, high speed internet, free parking, and a big private fenced in backyard this house can easily be your home away from home!

Cheerful 1-bedroom, red brick, historic home
Keep it simple at this peaceful, historic, and centrally-located place. This red brick home is a piece of long-standing history (built in 1928), on a quiet one way street. It is just 5 minutes away from the airport & University of Missouri Saint Louis, and just 15 minutes from down town and central west end. It is literally central to just about any place you wish to visit in the Saint Louis area! There’s convenient and free on-street parking too! Come enjoy your time at The Ruby Brick Stay!

Charming 2/1 in St Charles Historic Main Street
Come relax and play! Half a block from historic Main Street in City of St Charles. This stay is everything you could want. Cozy, charming, private with outdoor area for seating and dinning table. Off-street parking, laundry. Go shopping in the historic downtown shops, go to concerts, casinos or just stay in and enjoy! Walk to restaurants and the Katy Trail! Come be our guest! Or stay in put and cook the kitchen has everything you need! We are a strictly non smoking stay, inside or outside.

*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.

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 late 1800'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.

Serene Garden Cottage - Private Safe Parking
Mindfully renovated cozy bungalow offering a lush vibrant landscaped garden, meandering brick patio & deck overlooking waterfall pond w/ Koi fish. We lovingly restored our efficient space with a mix of old & new furnishings and updated appliances. A Romantic luxurious vibe ❤️ The perfect nest for two! Our quiet safe neighborhood is home to fabulous restaurants, bars, coffee shops and galleries. Close to everything including Hwys 40, 44, 55 . PLUS safe private parking

Family Friendly Home Near Parks and Dining
Enjoy a relaxing experience at our conveniently located home in St. Peters. This 3 bedroom 2.5 home is fully stocked and ready for your family to visit. The neighborhood is quiet and within walking distance of a lovely park with walking trails, a playground, and ball fields. We are also minutes away from groceries, dining, and the St. Peters Recplex. We cannot wait to welcome you to our space for your next get away!
Popular amenities for Chesterfield house rentals
House rentals with a pool

Willow Creek: Mid-Century Oasis

Private indoor pool & sauna

Blair's Pool House - Creve Couer Hot Tub Game Room

Arch View Luxury: Hottub-Pool-Sauna-Wine &Brkfst

"The Villa" at Villa Augusta in MO wine country

Spacious Home - Central Location - Amenity packed

Beekeeper's Cottage - Hot Tub, Heated Pool, Dog-fr

Roomy Oasis with hot tub on the Hill!
Weekly house rentals

Serenity Valley (No Cleaning Fee- No pets please)

Separate Entry Basement Apartment 1BR, 1BA

Cozy Home in Wentzville Sleeps 6 + Game Room

Gateway City Cottage

Main Street Hideaway

Granny's DOG House - KING BED - One of a Kind!

Pet & Child Friendly*Great Location*Ideal 4 Groups

Katy Trail Farmhouse - 3 bd/2.5 bath - Amazing!
Private house rentals

Cute 1BR, Safe, Secure, Private Everything!

Cozy & Comfortable home in a quiet neighborhood.

The Geyer Loft | Chic 1BR in Historic Soulard

Luxurious, spa-like retreat steps from Main St.

The Frenchtown Inn | 2BR Charmer

Eureka Garden of Life 71 Duplex unit #1

Guest: Clean Home, Safe Neighborhood, Dog Friendly

Serene & Cozy Cabin + LAKE! Near Purina & SixFlags
Quick stats about house rentals in Chesterfield

Total vacation rentals
Explore 10 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at G$8,365 GYD per night before taxes and fees

Verified guest reviews
Over 80 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chesterfield vacation rentals include wi-fi access

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

4.8 Average rating
Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!
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- Central West End
- Busch Stadium
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- City Museum
- St. Louis Aquarium at Union Station
- Missouri Botanical Garden
- Gateway Arch National Park
- Hidden Valley Ski Resort
- Forest Park
- Meramec State Park
- Castlewood State Park
- Soulard Farmers Market
- Cathedral Basilica of Saint Louis
- Saint Louis Science Center
- Missouri History Museum
- The Dome at America's Center
- Washington University in St Louis
- Saint Louis University
- Gateway Arch
- Laumeier Sculpture Park
- Meramec Caverns
- Anheuser-Busch Brewery




