Vacation rentals in Chesterfield, MO

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Chesterfield, MO vacation rentals
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Best Vacation rentals and Airbnb offers in Chesterfield, MO

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.

Charming Open 4bd And Screen-in Porch! Sleeps 10! - Chesterfield, MO
9.5 122 reviews
Chesterfield, MO
06/23 – 06/26
$549/nighttotal: $1647 (3 )

Charming Open 4bd And Screen-in Porch! Sleeps 10!

4 4
apartment , Bridgeton
This Bridgeton apartment is located in a quiet neighborhood within walking distance of Lindenwood University and a short drive from major St. Charles attractions. It has excellent user, location, and cleanliness ratings.
The apartment has 4 bedrooms, 2 bathrooms, and a floor area of 1910 square feet. It features an open kitchen and living room, a second family room downstairs, a covered screened-in patio, a garage, and driveway space for up to 3 additional vehicles. Guests can enjoy amenities such as air conditioning, a spa, internet, a kitchen with a fridge, freezer, microwave oven, and dishwasher, and a garden.
Cottage Of Castlewood - Chesterfield, MO
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.
Cozy West County Cottage - Chesterfield, MO
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.
The Global Getaway - Chesterfield, MO
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.

Best Chesterfield, MO vacation rentals with parking

2 Queen Beds | Non-smoking, Kitchen - Chesterfield, MO
9.7 23 reviews
Chesterfield, MO
07/08 – 07/13
$111/nighttotal: $555 (5 )

2 Queen Beds | Non-smoking, Kitchen

1 2
apartment , Maryland Heights
This Maryland Heights condo is located 6 miles from Hollywood Casino St. Louis and 5 miles from St. Louis Lambert International Airport.
This 300 sq ft apartment offers 1 bedroom, 1 bathroom, and accommodates up to 4 guests with two queen beds and an in-room kitchen featuring a refrigerator, microwave, oven, and stovetop, plus air conditioning and free on-site parking.
Main Street Balcony Apartment - Chesterfield, MO
9.4 168 reviews
Chesterfield, MO
08/22 – 08/25
$306/nighttotal: $918 (3 )

Main Street Balcony Apartment

2 6
apartment , Bridgeton
This 2-bedroom, 3-bathroom apartment is located on Main Street in the heart of downtown St. Charles, within walking distance of shops, restaurants, and entertainment. The apartment has a full parade balcony offering views of Main Street and is recently renovated with modern amenities and furnishings.
The apartment has excellent user, location, and cleanliness ratings. It can accommodate up to 8 guests and is dog-friendly. The apartment has a kitchen with a fridge, freezer, microwave oven, and dishwasher. It also has air conditioning, a terrace/balcony, a garden, and parking.
New Remodel In St. Charles - Sleeps 10! New Patio! Large Fenced-in Backyard! - Chesterfield, MO
9.6 73 reviews
Chesterfield, MO
08/22 – 08/25
$565/nighttotal: $1695 (3 )

New Remodel In St. Charles - Sleeps 10! New Patio! Large Fenced-in Backyard!

3 6
apartment , Bridgeton
This Bridgeton vacation home is located in the historic St. Charles Historic District, within easy walking distance of Lindenwood University and SSM Health St. Joseph Hospital. It has an excellent user rating.
This 3-bedroom, 2-bathroom house offers 1,600 square feet of living space and can accommodate up to 12 guests. It features an arcade/game room, a private garden, barbecue grills, a smoke-free environment, a fully equipped kitchen, free WiFi, and a sofa bed for additional sleeping arrangements.
Stylish 2br Retreat - Concrete & Canopy - Chesterfield, MO
Chesterfield, MO
07/08 – 07/13
$234/nighttotal: $1170 (5 )

Stylish 2br Retreat - Concrete & Canopy

1 2
apartment , Bridgeton
This 2-bedroom apartment in St. Charles is located 5.9 miles from Hollywood Casino St. Louis and 6.8 miles from St. Louis Lambert International Airport.
This 570 square foot rental accommodates up to 7 guests with 2 bedrooms, 1 bathroom, air conditioning, a fully equipped kitchen, and free WiFi, offering convenient access to St. Louis attractions.

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?

    Mid-century Funhouse, Saint Charles Escape Near Historic District and King Bed With Free Parking Perfect For Couples are the most popular Airbnb and vacation rentals in Chesterfield, MO among travelers.

  • 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?

    Among the Airbnbs in Chesterfield, MO, Mid-century Funhouse, King Bed With Free Parking Perfect For Couples and So Neat Apartment are the most popular ones.

  • 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.

Private 8 Acre Ranch Backs To 1850 Wooded Acre Missouri Conservation Reservation - Chesterfield, MO
10 2 reviews
Chesterfield, MO
07/02 – 07/04
$439/nighttotal: $878 (2 )

Private 8 Acre Ranch Backs To 1850 Wooded Acre Missouri Conservation Reservation

3 3
apartment , Wildwood
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.
Dreamy St Charles Retreat W/ Furnished Patio! - Chesterfield, MO
9.9 111 reviews
Chesterfield, MO
08/22 – 08/25
$385/nighttotal: $1155 (3 )

Dreamy St Charles Retreat W/ Furnished Patio!

3 6
house , Bridgeton
This St. Charles vacation home, near Bridgeton, is conveniently located 6.9 miles from Hollywood Casino St. Louis, 24 miles from the Gateway Arch, and 11 miles from St. Louis Lambert International Airport.
This 1800-square-foot house features three bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, a furnished patio, a garden, parking, and free Wi-Fi, comfortably accommodating families or groups.
Remodeled Kirkwood Guest House - Chesterfield, MO
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.
Omas Haus, Walk To Main Street - Chesterfield, MO
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.

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.

The Global Getaway | World-inspired 2-bedroom Stay - Chesterfield, MO
Chesterfield, MO
07/08 – 07/13
$241/nighttotal: $1205 (5 )

The Global Getaway | World-inspired 2-bedroom Stay

2 2
apartment , Bridgeton
This St. Charles Historic District condo offers walkable access to Historic Main Street and the First Missouri State Capitol Historic Site, located 1.5 miles from Westport Plaza and 3 miles from Mid Rivers Mall.
This 580 sq ft, 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features a fully stocked kitchen, dog-friendly policies, and global travel-inspired decor.
Private Entry Basement Suite  Pond View  Quiet Home  Pet Friendly Stays - Chesterfield, MO
9.8 9 reviews
Chesterfield, MO
07/08 – 07/13
$192/nighttotal: $960 (5 )

Private Entry Basement Suite Pond View Quiet Home Pet Friendly Stays

1 2
apartment , Cottleville
This St. Peters guesthouse, near Mid Rivers Mall Drive and a short drive from Highways 70 and 364, offers easy access to St. Charles (20 minutes) and Downtown St. Louis (40 minutes).
The 900-square-foot property features a private bedroom, living room with a 65-inch Smart TV, full kitchen, and can accommodate up to four guests, with additional sleeping arrangements available; enjoy nearby walking trails, the Hollywood Casino Amphitheatre, and other attractions.
Vivid Luxe Retreat | Luxury 2br Townhouse - Chesterfield, MO
Chesterfield, MO
08/22 – 08/25
$355/nighttotal: $1065 (3 )

Vivid Luxe Retreat | Luxury 2br Townhouse

1 6
house , Maryland Heights
This Maryland Heights rental home is located 3 miles from Highway 270 and a 5-minute drive to Creve Coeur Park, offering proximity to outdoor activities, shopping, and dining.
This pet-friendly, family-friendly house accommodates up to 6 guests with a fully stocked kitchen, air conditioning, a garden, a game room, a custom selfie wall, and outdoor seating with a BBQ grill.
Duplex Hideaway In St. Charles, Mo - Chesterfield, MO
10 5 reviews
Chesterfield, MO
07/08 – 07/13
$222/nighttotal: $1110 (5 )

Duplex Hideaway In St. Charles, Mo

1 2
apartment , Maryland Heights
This pet-friendly (dogs only, $100 cleaning fee) duplex in Maryland Heights' St. Charles Historic District on South Main Street offers easy access to local attractions like the Hollywood Casino Amphitheatre and the Historic Aircraft Restoration Museum.
This 650-square-foot one-bedroom, one-bathroom rental features a private patio, fenced backyard, modern amenities including Wi-Fi and a washer/dryer, and comfortably sleeps two guests.
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