Best Vacation rentals and Airbnb offers in Chesterfield, MO
9.9 51 reviews
Chesterfield, MO
08/22 – 08/25
$609/nighttotal: $1827 (3 )
Entire Home/ Stl Co-sleeps 6
1 6
apartment , Ballwin
Located in quiet Ballwin, this private ranch home is only 20 minutes from downtown St. Louis and St. Charles. It has been rated excellent for its location, cleanliness, and overall user experience. The home features two queen bedrooms, a fully equipped kitchen, and comfortable seating areas. It also has a 75" smart TV, a Sonos speaker, and a workout area. Guests can relax and enjoy the fresh air in the front courtyard/porch or the back patio with fenced yard.
9.5 26 reviews
Chesterfield, MO
06/23 – 06/26
$727/nighttotal: $2181 (3 )
Music House · Music House On Main Street At The Wine Garden
4 4
apartment , Maryland Heights
This charming home is located in St. Charles, Missouri, just a short walk from Ameristar Casino and a quick drive to the airport, offering easy access to the area's attractions. Guests have consistently rated this property "excellent" for its amenities and location. This 4-bedroom, 2-bathroom dwelling comfortably sleeps up to 10 guests. Enjoy a fully equipped kitchen, multiple bathrooms, a terrace, and a music room filled with instruments, perfect for a fun-filled getaway.
9.7 28 reviews
Chesterfield, MO
07/08 – 07/13
$101/nighttotal: $505 (5 )
1 Queen Bed | Non-smoking, Kitchen
1 2
apartment , Maryland Heights
This Maryland Heights studio apartment is located 5 miles from St. Louis Lambert International Airport, 6.2 miles from Hollywood Casino St. Louis, and 11.2 miles from Forest Park. This 300 sq ft rental features a fully equipped kitchen, air conditioning, complimentary WiFi, and on-site parking, with a guest capacity of two.
Chesterfield, MO
06/23 – 06/26
$247/nighttotal: $741 (3 )
The Brick & Beam 3rd Floor Apartment
2 4
apartment , Bridgeton
The Brick & Beam 3rd Floor Apartment in St. Charles is located approximately 6 miles from St. Louis Lambert International Airport and within 23 miles of St. Louis attractions like the Gateway Arch and Hollywood Casino. This 540 square foot condo offers 2 bedrooms, 1 bathroom, a full kitchen with a dishwasher and microwave, air conditioning, and accommodates up to 7 guests, with pets allowed.
10 229 reviews
Chesterfield, MO
08/22 – 08/25
$296/nighttotal: $888 (3 )
1790's Renovated Barn, Main Street St. Charles, Hot Tub In Private Backyard!
2 6
apartment , Maryland Heights
The Red Barn Guest House is located in the St. Charles Historic District, a short walk from the charming shops and restaurants of Historic St. Charles. This charming accommodation has received excellent user ratings and is perfect for families or groups. The farmhouse has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It offers a blend of modern amenities and rustic charm, including a private hot tub, a kitchenette with stainless steel appliances, and a variety of entertainment options.
10 13 reviews
Chesterfield, MO
08/22 – 08/25
$450/nighttotal: $1350 (3 )
Hot Tub Retreat. 2 King Beds. Game Room Fun
3 6
apartment , Cottleville
This Cottleville vacation home is conveniently located near Mid Rivers Mall, Barnes-Jewish St. Peters Hospital, and Kokomo Joe's Family Fun Center, all within six miles. This three-bedroom, two-bathroom house sleeps six guests and includes in-unit laundry, a fitness center, and essential amenities like a hair dryer and iron.
Chesterfield, MO
07/02 – 07/04
$275/nighttotal: $550 (2 )
The Retro Retreat 3rd Floor Apartment
2 3
apartment , Bridgeton
This Bridgeton apartment is located 6.8 miles from St. Louis Lambert International Airport and 5.9 miles from Hollywood Casino St. Louis. This 540 sq ft rental features two bedrooms, one bathroom, a full kitchen with a dishwasher and microwave, and accommodates up to seven guests with on-site parking and complimentary WiFi.
9.0 34 reviews
Chesterfield, MO
07/08 – 07/13
$213/nighttotal: $1065 (5 )
Stay On Main Historic Studio
1 2
studio , Bridgeton
This apartment is located in the St. Charles Historic District, just a short walk from Historic Main Street, the Missouri River, and the First Missouri State Capitol Historic Site. It has received excellent ratings from previous guests. The apartment has one bedroom and one bathroom, and can accommodate up to two guests. It includes amenities like a coffee/tea maker, a TV, a refrigerator, a hair dryer, an iron/ironing board, and internet access.
8.6 14 reviews
Chesterfield, MO
06/26 – 06/28
$382/nighttotal: $764 (2 )
Historic 5th Street House - Fully Rehabbed # 2
2 5
apartment , Bridgeton
This fully renovated vacation home in the St. Charles Historic District is conveniently located near the Katy Trail, Historic Main Street, and St. Charles Street, all offering nightlife, shopping, and restaurants, as well as a short drive from the Hollywood Casino Amphitheatre and the Centene Community Ice Center. This two-bedroom, one-bathroom house comfortably accommodates up to six guests and includes amenities such as air conditioning, parking, internet, and a secure, lit parking lot.
Chesterfield, MO
07/08 – 07/13
$228/nighttotal: $1140 (5 )
The Global Getaway
2 2
apartment , Bridgeton
This Bridgeton condo is located in a quiet district, a short distance from key city attractions and local amenities. This 580 sq ft unit offers 1 bedroom, 1 bathroom, and accommodates up to 4 guests, featuring a full kitchen with a dishwasher and microwave, complimentary Wi-Fi, and air conditioning.
9.8 12 reviews
Chesterfield, MO
07/08 – 07/13
$206/nighttotal: $1030 (5 )
Cozy West County Cottage
1 2
apartment , Maryland Heights
This three-bedroom Maryland Heights cottage, located 10 minutes from St. Louis Lambert International Airport and under 30 minutes from various St. Louis attractions, offers a peaceful retreat near major transportation and sightseeing. The family-friendly home features a king and two queen beds, one bathroom, a full kitchen, keyless entry, and accommodates up to five guests; no cleaning fee is charged.
Chesterfield, MO
06/23 – 06/26
$198/nighttotal: $594 (3 )
Omas Haus, Walk To Main Street
3 4
house , Bridgeton
Omas Haus is a house located in St. Charles, 6 miles from Hollywood Casino St. Louis and 17 miles from Forest Park. This accommodation offers 2 bedrooms, 1 bathroom, and can host up to 15 guests with amenities including internet, a kitchen, air conditioning, a balcony, and free private parking.
Top Vacation Rentals for Families in Chesterfield, MO
The right family vacation rental in Chesterfield, MO makes all the difference, keeping you close to top city attractions.
Chesterfield, MO
07/02 – 07/04
$263/nighttotal: $526 (2 )
Hearth & Harvest - Cozy Farmhouse-inspired 2bdr
2 3
apartment , Bridgeton
This 2-bedroom apartment in St. Charles is located 6.8 miles from St. Louis Lambert International Airport and 5.9 miles from Hollywood Casino St. Louis. This 740 square foot residence accommodates up to 4 guests with a fully equipped kitchen, air conditioning, and a cozy, farmhouse-inspired interior.
10 1 review
Chesterfield, MO
07/08 – 07/13
$595/nighttotal: $2975 (5 )
Blue Boho Music And Meme House Four Bedroom Home With Arcade Near Westport Plaza
1 2
house , Maryland Heights
This four-bedroom house near Westport Plaza in Maryland Heights, Missouri offers convenient access to shopping and dining. The 1,260-square-foot home sleeps up to 19 guests and features a fully equipped kitchen, free Wi-Fi, private parking, a flat-screen TV, and an on-site arcade.
Chesterfield, MO
06/23 – 06/26
$220/nighttotal: $660 (3 )
Condo ∙ 1 Bedroom ∙ 4 Guests
1 4
apartment , O'Fallon
This O'Fallon suite offers convenient access to outdoor recreation at Busch Conservation Area, family attractions like the Sophia Sachs Butterfly House, and is 1 mile from Progress West Hospital and 2 miles from the Hollywood Casino Amphitheater. This family-friendly 1-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully-equipped kitchen with a fridge, microwave, and dishwasher, plus complimentary Wi-Fi, parking, and a seasonal outdoor pool.
9.7 71 reviews
Chesterfield, MO
08/22 – 08/25
$374/nighttotal: $1122 (3 )
3br Family+game Retreat 8 Min Stl Airport/westport
1 6
apartment , Maryland Heights
This Maryland Heights house rental is conveniently located ten minutes from Lambert International Airport and near various restaurants. The newly renovated three-bedroom, two-and-a-half-bathroom home sleeps seven guests and features a game room with foosball, Jenga, an electronic dartboard, and a smart TV, plus a fully equipped kitchen and in-unit laundry.
Best Chesterfield, MO vacation rentals with parking
9.2 15 reviews
Chesterfield, MO
06/26 – 06/28
$308/nighttotal: $616 (2 )
Rhythm Loft Above The Honky Tonk
1 5
apartment , Bridgeton
This two-bedroom, one-bathroom apartment rental in St. Charles' Historic District is steps from Main Street, near the First Missouri State Capitol Historic Site and the Missouri River. The pet-friendly unit, located above a bar with live music and offering a shared patio, sleeps six and includes a fridge, microwave, dishwasher, air conditioning, and a terrace.
Chesterfield, MO
07/08 – 07/13
$217/nighttotal: $1085 (5 )
The Bourbon & Brass - Speakeasy-inspired 2bdr
2 2
apartment , Bridgeton
This speakeasy-inspired 2-bedroom apartment in St. Charles is located approximately 6 miles from Hollywood Casino St. Louis and 7 miles from St. Louis Lambert International Airport. This 750 square foot unit accommodates up to 7 guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, free Wifi, and parking.
Chesterfield, MO
08/22 – 08/25
$224/nighttotal: $672 (3 )
Free Breakfast. Pool & Gym. Near Progress West Hospital!
1 6
apartment , O'Fallon
This O'Fallon apartment is situated within 3 miles of Busch Conservation Area, Progress West Hospital, and Hollywood Casino Amphitheater, offering convenient access to St. Louis attractions. This 1-bedroom, 1-bathroom rental accommodates up to 6 guests and features a fully-equipped kitchen, complimentary Wi-Fi and parking, a seasonal outdoor pool, and 24-hour business and fitness centers.
Chesterfield, MO
07/08 – 07/13
$242/nighttotal: $1210 (5 )
Stylish 2br Retreat | Concrete & Canopy
2 2
apartment , Bridgeton
This Bridgeton condo is located in the St. Charles Historic District, offering 0.2 miles walkability to Main Street shops and dining, and is close to the riverfront. This 570 sq ft, 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully stocked kitchen, air conditioning, Wi-Fi, and is dog-friendly for a fee, with attractions like Pelican Island Natural Area and Frontier Park nearby.
Frequently Asked Questions about vacation rentals in Chesterfield, MO
What are the top family-friendly attractions in Chesterfield, MO?
The Chesterfield Family Aquatic Center is a great place to cool off on a hot day with water slides, a lazy river, and a splash pad. If you're looking for something a little more adventurous, the Magic House is an interactive children's museum with exhibits that encourage learning through play. And if you're looking for a more traditional family outing, the Faust Park is a beautiful park with a playground, walking trails, and a lake.
What are the best Airbnb and vacation rentals in Chesterfield, MO?
When is the best time to book a vacation rental in Chesterfield, MO?
The best time to book a vacation rental in Chesterfield is during the shoulder seasons, like spring and fall. You'll get the best prices and avoid the crowds, but you'll still have plenty of sunshine and warm weather to enjoy. If you're looking for a more festive experience, you can also book during the summer for the Chesterfield Amphitheater concerts or during the winter for the Christmas in the Valley events.
What are the most popular Airbnbs in Chesterfield, MO?
What are the best budget-friendly activities in Chesterfield, MO?
The Faust Park is a great place to spend a day outdoors without spending a dime. The park has walking trails, a playground, a lake, and a historic village. You can also check out the free concerts and events at the Chesterfield Amphitheater. And if you're looking for a unique experience, the Chesterfield Museum and Historical Society offers free tours of the historic Chesterfield City Hall.
What are the best vacation rentals with a pool in Chesterfield, MO?
What are the best restaurants with local dishes in Chesterfield, MO?
For a taste of local flavor, you can't go wrong with The Clover and the Bee. They're known for their farm-to-table dishes and their commitment to using fresh, seasonal ingredients. If you're looking for something a little more casual, The Blue Owl is a great option for burgers, sandwiches, and salads. And for a truly unique dining experience, try the The Pasta House Co. in Chesterfield, which is known for its delicious pasta dishes and its lively atmosphere.
What are the best rentals for families and kids in Chesterfield, MO?
What are the best walking or cycling routes in Chesterfield, MO?
The Chesterfield Valley is a great place to walk or bike, with miles of paved trails that wind through parks and residential areas. The Faust Park is another great option for a leisurely stroll or bike ride, with scenic trails that wind through the woods and along the lake. If you're looking for a more challenging ride, the Katy Trail is a 240-mile rail trail that runs through Chesterfield and into St. Louis.
What are the best rentals or Airbnbs with a jacuzzi in Chesterfield, MO?
Are there pet-friendly attractions in Chesterfield, MO?
Yes, there are many pet-friendly attractions in Chesterfield. Faust Park is a great place to walk your dog, and many of the restaurants in the Chesterfield Valley have outdoor seating that is pet-friendly. You can also find dog parks in several neighborhoods around the city.
Destinations nearby
Best Vacation Rentals with Balconies in Chesterfield, MO
Start your morning right with a vacation rental in Chesterfield, MO featuring a private balcony and stunning views.
10 82 reviews
Chesterfield, MO
07/08 – 07/13
$239/nighttotal: $1195 (5 )
Remodeled Kirkwood Guest House
1 2
apartment , Kirkwood
This one-bedroom apartment is conveniently located in Kirkwood, just a short distance from the Magic House, Laumeier Sculpture Park, and the Museum of Transportation, making it an ideal base for exploring the area. The apartment has received excellent user ratings, indicating a positive experience for previous guests. The apartment is perfect for families or small groups, comfortably accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, a balcony, a Smart TV, and access to barbecue grills, providing everything you need for a comfortable and enjoyable stay.
This 3-bedroom, 2-bathroom vacation rental in Wildwood, Missouri, offers a private retreat on 8 acres bordering Rockwoods Reservation state conservation land, with Six Flags St. Louis and Hidden Valley Ski Resort 8 miles away. This 2000 square foot house accommodates up to 8 guests with three queen beds and a queen futon, featuring a fully equipped kitchen, outdoor fire pit, Weber grill, and welcomes horses with trailer space.
9.2 44 reviews
Chesterfield, MO
06/23 – 06/26
$380/nighttotal: $1140 (3 )
Cottage Of Castlewood
5 4
apartment , Ballwin
This Ballwin cottage, located adjacent to Castlewood State Park, provides easy access to hiking trails and is also conveniently close to Ballwin's restaurants and shops. This five-bedroom, three-bathroom house sleeps eight guests and features a game room with a pool table, three family areas, a rooftop deck with park views, and direct access to Castlewood State Park.
Chesterfield, MO
08/22 – 08/25
$257/nighttotal: $771 (3 )
The Barker Bungalow
1 6
house , Bridgeton
The Barker Bungalow, a house in Bridgeton, is located in St. Charles, 5.2 miles from Hollywood Casino St. Louis and 5.6 miles from St. Louis Lambert International Airport. This one-bedroom, one-bathroom bungalow accommodates up to 11 guests and offers free private parking, complimentary WiFi, a fully equipped kitchen, air conditioning, and a balcony.
Our Favorite Pet-Friendly Vacation Rentals in Chesterfield, MO
Stay in a pet-friendly vacation rental in Chesterfield, MO situated near dog parks and city walks, ensuring a comfortable stay for both you and your pet.
Chesterfield, MO
06/23 – 06/26
$233/nighttotal: $699 (3 )
Hearth & Harvest | Cozy Farmhouse-inspired 2bdr
2 4
apartment , Bridgeton
This 2-bedroom, 1-bathroom apartment is located in the St. Charles Historic District, offering walkable access to Main Street's shops, dining, and the riverfront, with Hollywood Casino Amphitheatre and Missouri Artists on Main just 0.5 miles away. This 740 sq ft rental accommodates up to 4 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and allows pets for a fee.
9.6 111 reviews
Chesterfield, MO
08/22 – 08/25
$604/nighttotal: $1812 (3 )
Lots Of Space! Central To St. Charles & Stl
5 6
apartment , Maryland Heights
This five-bedroom, two-bathroom house, conveniently located off Highway 270 in Maryland Heights, offers easy access to area attractions. The 14-guest home features two living areas, a fully equipped kitchen with a dishwasher, a fenced backyard with a patio, six TVs, and amenities like a foosball table and game table, perfect for families or groups.
Chesterfield, MO
07/08 – 07/13
$244/nighttotal: $1220 (5 )
Salt & Serenity Coastal-inspired 2-bedroom
2 2
apartment , Bridgeton
This 2-bedroom, 1-bathroom condo in Bridgeton is situated in the St. Charles Historic District, offering a 2-minute walk to Main Street's shops and dining, as well as the riverfront. This 610 sq ft rental accommodates up to 4 guests and features a full kitchen with a fridge, microwave, and dishwasher, plus air conditioning, parking, and it is dog-friendly.
9.0 3 reviews
Chesterfield, MO
08/22 – 08/25
$275/nighttotal: $825 (3 )
Fifth Street Retreat By Staylage
2 6
house , Bridgeton
Fifth Street Retreat, a recently renovated vacation home in St. Charles, offers convenient access to both local amenities and attractions like the Hollywood Casino St. Louis (5.7 miles away) and the Gateway Arch (25 miles away). This 800-square-foot house features two bedrooms, one bathroom, and sleeps up to 11 guests, boasting amenities such as free Wi-Fi, a fully equipped kitchen with a dishwasher, and outdoor seating; nearby cycling opportunities are also available.
