
House holiday 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.

Sweet Escape Near Historic Main Street & MO River
Discover your Sweet Escape in this charming 4-bedroom bungalow, just a 3-minute drive (or 20-minute walk) to Historic Main Street's cobblestone streets, boutique shops, restaurants, and lively events! Perfect for exploring St. Charles & St. Louis, the home boasts a game-filled basement with a pool table, ping-pong, foosball, & darts. Unwind with yard games, a fire pit, or cozy up indoors with board games and DVDs. Rest easy on plush beds with room-darkening curtains for a perfect night's sleep.

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!

Tompkins Street Retreat
Relax in this two-bedroom, two-bath house with a backyard patio and firepit with a privacy fence. Walk to unique shopping and entertainment on Historic St. Charles Main Street. Local wineries and St. Louis attractions are a short drive away. Enjoy a comfortable living room with a large TV and a fully equipped kitchen for special meals. Unwind after an active day with a meal, drinks under the pergola, and a great night's sleep in our king-size bed. We also offer FREE off-street/garage parking.

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.

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.

St. Louis Home away from Home!
Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

*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.

2 Bdrm Home Less than 6 miles from Lambert Airport
Your family will have easy commute to surrounding restaurants and other eye catching places such as: -Less than 6 miles to St Louis Zoo -Less than 17 miles to Gateway Arch -Less than 15 miles to Bush Stadium -Less than 14 miles to STL Soccer Stadium -Less than 15 miles to Enterprise Center -Less than 13 miles to Hollywood Casino -Less than 9 miles to Walmart -Less than 1 mile to Save a Lot (Grocery) -Less than 6 miles to Lambert Airport -Less than 6 miles to Wholes Food Market
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Willow Creek: Mid-Century Oasis

Route 66 SuperHost Retreat • Hot Tub • 6 Acres

Private indoor pool & sauna

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

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

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

Family Friendly Townhouse

ZOO, Wash U, close to Clayton,Parking & Safe!

Updated Farmhouse 2 bdrm 2bds 1 bath

ArtBnB: Enjoy the Curated Comforts of Home

Main Street Hideaway

Pet & Child Friendly*Great Location*Ideal 4 Groups

Safe home in a quiet neighborhood near I 44

Charming Cottage Near Forest Park in Quiet Area
Private house rentals

Separate Entry Basement Apartment 1BR, 1BA

Cozy & Comfortable home in a quiet neighborhood.

The Little House.

Luxurious, spa-like retreat steps from Main St.

Victorian Gem Steps from Main St - Sleeps 9 & Pets

Sparkling Vintage Charmer, King Bed, Quiet Comfort

3+ private acres, Koi fish pond, garage parking

Two King and Two Twin Beds in French Town
Quick stats about house rentals in Chesterfield

Total holiday rentals
Explore 10 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 80 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Chesterfield holiday rentals include wifi 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
- Missouri Botanical Garden
- Gateway Arch National Park
- St. Louis Aquarium at Union Station
- Hidden Valley Ski Resort
- Forest Park
- Castlewood State Park
- Meramec 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
- Gateway Arch
- Meramec Caverns
- Fabulous Fox
- The Pageant
- Saint Louis University




