
House vacation rentals in Chesterfield
Find and book unique houses on Airbnb
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 $50 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

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

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!
ValueFamilyBreakfast

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
LocationValueGrill

Pet & Child Friendly*Great Location*Ideal 4 Groups
Stay Awhile is more than a place to stay—it’s a memory maker! This spacious St. Louis vacation rental is tucked in a fantastic neighborhood & less than 30 minutes from top St. Louis attractions-like the Zoo & Arch! Designed for families, groups & pets, it offers cozy beds, a well-stocked kitchen & plenty of space for everyone. A one-of-a-kind Eye Spy game is hidden throughout the décor, making the home part of the adventure. Perfect for those who love comfort, convenience & a touch of whimsy.
LocationFamilyBackyard

Cottage on Historic Main St- Low Cleaning Fee
MESSAGE FOR SHORT STAY DISCOUNT Walk to everything on Historic Main Street St. Charles! Stay in a stylish 2BR steps from top dining, shops, nightlife & Ameristar Casino. 12 mins to STL Airport. Fast Wi-Fi, Smart TV’s, full kitchen, free parking & easy self check-in. Perfect for couples, weekend getaways & business stays. Unbeatable location, step outside directly onto Main Street in this vibrant, walkable district. Check out our 5★ reviews! Come check our top rated place in St. Charles, MO.
FamilyLocationAccuracy

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.
ValueFamilyComfort

Cozy Cottage in a Quiet City Neighborhood!
Please inquire for longer stay rates. This 650sq.ft quaint cottage has EVERYTHING! Centrally located this sought after historical neighborhood, DOGTOWN!, is just minutes from Forest Park and a short drive to all of STL's BEST ATTRACTIONS! This charmer has all the amenities you could hope for @ your HOME away from home! 2 Bedrooms with a Queen Bed in each, 3 Smart TV's, a backyard patio, KEYLESS Self Entry, fully equppied kitchen with SS appliances, MAIN FLOOR LAUNDRY and fully UPDATED BATH!
FamilyValueWalkability

Wooded Oasis with Free Bottle of wine+brkfst
Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.
ValueLocationParking

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.
ValueLocationBackyard

*NEW HotTub* The Jewel on 5th-2br2b-near 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.
LocationFamilyKitchen

Great Fam Friendly Home w/ Lrg Deck & Yard
**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station
LocationValueCondition

2bed/2bath Walk Main St Shops Eateries & Bars!
The "Lion House" is a completely restored charming 1930s home located in the heart of St. Charles’ National Historic District & has tons of amenities. Explore all that St. Charles has to offer…perfect place to stay (Lindenwood University - only 1 mile away) and play as you are only steps from the walkable historic Main Street lined w/boutiques, eateries, gourmet shops, Katy Trail (bike trail & rentals), pubs & nightclubs! This unique place has a style all its own.
LocationValueWalkability

Little House By Main St -5 4K TV's- 1-75 Inch -1GB
Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!
LocationFamilyTV
Popular amenities for Chesterfield house rentals
House rentals with a pool

Sunset Mountain Privacy
LocationValuePool

Honeymoon Suite at Camp Skullbone In The Woods
ValueLocationAccuracy

Spacious Home - Heated Pool Open - Amenity Packed
ValueLocationBathroom

Roomy Oasis with hot tub on the Hill!
LocationFamilyCheck-in

Heated Saltwater Pool+Hot Tub! Great location!
LocationValueHot tub

Innsbrook Luxe Escape - Spacious Retreat, Hot Tub
LocationValueComfort

Tower Grove Oasis #1 + King Bed + Queen Bed+ Patio
LocationValuePool

Cabin+LAKE! Fish-swim-kayak*Near Purina & SixFlags
LocationFamilyAccuracy
Weekly house rentals

New: Cozy Cottage Near The Hill
ValueLocationAccuracy

The St. Louie House in Fenton w/deck & large yard!
ValueLocationIndoor spaces

Safe home in a quiet neighborhood near I 44
LocationFamilyTV

Family Friendly Home Near Parks and Dining
ValueFamilyAccuracy

The Soulard Cottage | There Is Only One
LocationValueWalkability

Gateway City Cottage
FamilyLocationSleep quality

The Ladybug Inn
LocationValueLaundry

Tranquil three-bedroom home in central St. Louis
FamilyLocationHot tub
Private house rentals

Luxurious, spa-like retreat steps from Main St.
LocationIndoor spacesWalkability

Country Quiet Suburban Haven
FamilyLocationCheckout

Spacious 3BR Ranch Near I-64 & Hwy K
LocationFamilySleep quality

Classy + Fun 4bd/1.5bth | Patio Dining | Game Room
LocationFamilyKitchen

Hot Tub Gazebo | Game Room | 2 Kings | Sleeps 8
ValueLocationHospitality

Pets Welcome ~ Long Stay Discounts ~ Game Room
FamilyLocationQuiet

Your Quiet Home in the St. Louis Suburbs Awaits
LocationFamilyCleanliness

Meriwether Cottage
LocationFamilyComfort
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- Busch Stadium
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- Six Flags St. Louis
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- Gateway Arch
- City Museum
- Missouri Botanical Garden
- Washington University in St Louis
- Meramec State Park
- Forest Park
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- Saint Louis University
- The Pageant
- Castlewood State Park
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- Soulard Farmers Market
- Saint Louis Science Center
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- Westport Plaza
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