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-Rated Vacation Rentals near the City Center in Chesterfield, MO

These vacation rentals in the downtown area of Chesterfield, MO offer unbeatable walking access to vibrant local life, dining, and culture.

2 Queen Beds | Mobil Access Tub Nsmk Kitchen - Chesterfield, MO
10 43 reviews

2 Queen Beds | Mobil Access Tub Nsmk Kitchen

apartment, Maryland Heights
This Studio 6 Extended Stay apartment is located on a lake in Maryland Heights, 6 miles from Hollywood Casino St. Louis and 5 miles from St. Louis Lambert International Airport.
This 300 square foot studio unit accommodates up to 4 guests with a sofa bed, features a full kitchen with a fridge, microwave, oven, and stovetop, and offers complimentary WiFi and air conditioning.
‘Bross Brother's Cabin’ W/ Wraparound Porch! - Chesterfield, MO
9.9 104 reviews

‘Bross Brother's Cabin’ W/ Wraparound Porch!

cabin, Cottleville
The Bross Brothers Cabin with Wraparound Porch! is located in Cottleville, a short drive from both Hollywood Casino St. Louis and Six Flags St. Louis, making it a convenient base for exploring the region. The cabin has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The cabin spans 1800 square feet and comfortably accommodates up to 8 guests in its two bedrooms. The cabin offers a fully equipped kitchen, air conditioning, a spacious wraparound porch, free Wi-Fi, a garden, and parking, ensuring a comfortable and enjoyable stay.
2 Queen Beds | Non-smoking, Kitchen - Chesterfield, MO
9.7 23 reviews

2 Queen Beds | Non-smoking, Kitchen

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.
1 Queen Bed | Non-smoking, Kitchen - Chesterfield, MO
9.5 29 reviews

1 Queen Bed | Non-smoking, Kitchen

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.

Best Chesterfield, MO vacation rentals with air conditioning

Private Entry Basement Suite  Pond & Farm View  Pet Friendly  St Peters - Chesterfield, MO
10 14 reviews

Private Entry Basement Suite Pond & Farm View Pet Friendly St Peters

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.
Hansons Stationhouse    Historic St. Charles - Chesterfield, MO
9.7 227 reviews

Hansons Stationhouse Historic St. Charles

apartment, Bridgeton
This St. Charles, Missouri vacation home, situated in the St. Charles Historic District, is within a 15-minute walk of Lindenwood University, Historic Main Street, and SSM Health St. Joseph Hospital, with easy access to the First Missouri State Capitol and the Missouri River.
This five-bedroom, two-bathroom house sleeps seven guests and boasts a fully equipped kitchen, a jacuzzi, a fitness center, and a terrace, all within a pet-friendly environment.
Charming Duplex On Main - Chesterfield, MO
10 25 reviews

Charming Duplex On Main

apartment, Maryland Heights
This St. Charles Historic District apartment rental offers convenient access to Historic Main Street and Ameristar Casino St. Charles (both under a 10-minute walk), plus the Lewis & Clark Boathouse and Nature Center and First Missouri State Capitol Historic Site (within 15 minutes).
This 650-square-foot, one-bedroom, one-bathroom unit sleeps two guests and includes a fully equipped kitchen, in-unit laundry, and on-site parking.
Cottage On Main St- Low Cleaning Fee - Chesterfield, MO
10 9 reviews

Cottage On Main St- Low Cleaning Fee

apartment, Bridgeton
This two-bedroom, one-bathroom apartment rental in St. Charles's Historic District, a short walk from the Old Stone Chapel and Lewis & Clark Museum, offers easy access to Main Street's shops and restaurants.
The 2-bedroom duplex features a fully equipped kitchen with a Keurig coffee maker, smart TV's in each bedroom, a smart lock, and accommodates up to four guests, with parking included; nearby attractions include the Streets of St. Charles and Ameristar Casino.

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.

Popular destinations

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.

Omas Haus, Walk To Main Street - Chesterfield, MO
9.5 2 reviews

Omas Haus, Walk To Main Street

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.
Retro Ranch With Private Indoor Pool & Sauna St Louis, Mo - Chesterfield, MO
10 256 reviews

Retro Ranch With Private Indoor Pool & Sauna St Louis, Mo

apartment, Ballwin
This West County ranch home for rent in Ballwin is located within walking distance of Candicci's Italian restaurant, Target, Starbucks, and Vlasis Park, and a five-minute drive from several grocery stores and Walmart. It is also in proximity to local attractions such as the St. Louis Zoo (18 miles), Busch Stadium/downtown (23 miles), Myseum (3 miles), Magic House (13 miles), and Six Flags (18 miles). The home has an excellent user rating.
The home has a floor area of 3050 square feet, 4 bedrooms, 4 bathrooms, and a guest capacity of 10. It features a private indoor pool, sauna, steam shower, and bath adjoining the master bedroom suite, as well as a private changing room, poolside dining booth, and fireplace. Other amenities include free Wi-Fi and cable television in four rooms, a tennis court, a garden, a terrace or balcony, air conditioning, a swimming pool, a Jacuzzi, a sauna, a spa, a kitchen with a fridge, microwave oven, and dishwasher, and parking.
King’s Corner Retreat By Staylage - Chesterfield, MO
No reviews

King’s Corner Retreat By Staylage

house, Weldon Spring
King's Corner Retreat is a house located in Harvester, Weldon Spring, 13 miles from Hollywood Casino St. Louis and 26 miles from Six Flags St. Louis, with St. Louis Lambert International Airport 14 miles away.
This 1860 square foot home accommodates up to 19 guests in 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, fireplace, on-site parking, and free Wi-Fi.
Luxurious 2-bedroom Abode With Elevated Comforts Near Main Street - Chesterfield, MO
8.0 9 reviews

Luxurious 2-bedroom Abode With Elevated Comforts Near Main Street

apartment, Bridgeton
This St. Charles apartment rental, conveniently located near Main Street and a short drive from the Hollywood Casino St. Louis (6.8 miles) and major St. Louis attractions like the St. Louis Zoo and Forest Park (within 20 miles), offers easy access to both city excitement and suburban tranquility.
The 760-square-foot, two-bedroom, one-bathroom unit sleeps up to 11 guests and includes amenities such as a fully equipped kitchen, in-unit laundry, air conditioning, a balcony, free Wi-Fi, and 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.

Sage Haven Ranch Retreat, Yard, Fire Pit, Bbq, Office Space, Close To Shopping - Chesterfield, MO
10 26 reviews

Sage Haven Ranch Retreat, Yard, Fire Pit, Bbq, Office Space, Close To Shopping

apartment, O'Fallon
This St. Peters vacation home, located three miles from Bowlero St. Peters and within six miles of the Alligator Creek Aquatic Center and Mid Rivers Mall, offers a family-friendly escape near popular attractions. This 2000-square-foot house features three bedrooms, three bathrooms, sleeps eight guests, and includes amenities such as a fully equipped kitchen, a patio, free Wi-Fi, an on-site game room, and a backyard with barbecue grills.
New Remodel In St. Charles - Sleeps 10! New Patio! Large Fenced-in Backyard! - Chesterfield, MO
9.6 79 reviews

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

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.
Office And 5 Br, Updated Bathrooms, Movie Theater In Creve Coeur - Chesterfield, MO
8.4 24 reviews

Office And 5 Br, Updated Bathrooms, Movie Theater In Creve Coeur

apartment, Creve Coeur
This Creve Coeur vacation home, near Bellerive Country Club (0.7 miles) and within 3 miles of Mercy Olive Mason MOB and St. Luke's Hospital, offers convenient access to local amenities and attractions.
This 4000-square-foot house features a spacious six-bedroom layout accommodating up to 10 guests, complete with a Jacuzzi, tennis court, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
The Retro Retreat 3rd Floor Apartment - Chesterfield, MO
No reviews

The Retro Retreat 3rd Floor Apartment

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.

Best Chesterfield, MO vacation rentals with parking

Ameristar Casino Resort And Spa - Chesterfield, MO
8.6 1136 reviews

Ameristar Casino Resort And Spa

resort, Maryland Heights
Walk To St. Charles Entertainment - Chesterfield, MO
9.0 11 reviews

Walk To St. Charles Entertainment

apartment, Maryland Heights
Stylish1brstudiocleanquietandcozy - Chesterfield, MO
10 3 reviews

Stylish1brstudiocleanquietandcozy

studio, Weldon Spring
Dog-friendly 2br | Near Streets Of St Charles - Chesterfield, MO
9.4 133 reviews

Dog-friendly 2br | Near Streets Of St Charles

house, Maryland Heights

Compare Luxury Vacation Rentals in Chesterfield, MO

Elevate your travel experience with a luxury rental in Chesterfield, MO, where high-end design meets a prime location.

Studio Flat ∙ 1 Bedroom ∙ 4 Guests - Chesterfield, MO
No reviews

Studio Flat ∙ 1 Bedroom ∙ 4 Guests

studio, O'Fallon

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.

Charming Duplex On Main - Chesterfield, MO
9.7 3 reviews

Charming Duplex On Main

apartment, Maryland Heights
Walk To St Charles Main St. Shops, Eateries & Bars! - Chesterfield, MO
10 87 reviews

Walk To St Charles Main St. Shops, Eateries & Bars!

apartment, Bridgeton
The Headliner Suite On Main Street - Chesterfield, MO
9.6 48 reviews

The Headliner Suite On Main Street

apartment, Maryland Heights
Historic 1805 Main Street 2br - Chesterfield, MO
9.7 213 reviews

Historic 1805 Main Street 2br

apartment, Bridgeton

Explore Vacation Rentals with a Pool in Chesterfield, MO

Staying in a vacation rental or Airbnb with a pool in Chesterfield, MO ensures a proper swim is always a convenient part of your city stay.

Free Breakfast. Pool & Gym. Near Progress West Hospital! - Chesterfield, MO
No reviews

Free Breakfast. Pool & Gym. Near Progress West Hospital!

apartment, O'Fallon
King Suite. Free Breakfast. Pool & Gym. Your Next Trip! - Chesterfield, MO
10 1 review

King Suite. Free Breakfast. Pool & Gym. Your Next Trip!

apartment, O'Fallon
Monthly Stays Luxe Des Peres Suite With Complimentary Starbucks Onsite! - Chesterfield, MO
No reviews

Monthly Stays Luxe Des Peres Suite With Complimentary Starbucks Onsite!

apartment, Town and Country
Fenton Oasis - Private Pool And Garden - Chesterfield, MO
9.2 5 reviews

Fenton Oasis - Private Pool And Garden

apartment, Fenton

Search Vacation Rentals with Jacuzzi in Chesterfield, MO

Unwind after exploring the city with a private hot tub in your own Chesterfield, MO vacation rental.

The Getaway House | St Charles 4br Sleeps 11 Game Room | Hot Tub | Mercer Stays - Chesterfield, MO
10 8 reviews

The Getaway House | St Charles 4br Sleeps 11 Game Room | Hot Tub | Mercer Stays

apartment, Maryland Heights
Office + 5 Br, Movie Theater , Creve Coeur -10 Sleep Surface - Chesterfield, MO
8.8 19 reviews

Office + 5 Br, Movie Theater , Creve Coeur -10 Sleep Surface

house, Creve Coeur
The Stadium By Mercer Stays | Private 2.2acre Sports Estate For Teams & Families - Chesterfield, MO
No reviews

The Stadium By Mercer Stays | Private 2.2acre Sports Estate For Teams & Families

apartment, Maryland Heights
Elegant 5,000 Sf  House Nestled In Wooded Area. - Chesterfield, MO
8.7 3 reviews

Elegant 5,000 Sf House Nestled In Wooded Area.

apartment, Wildwood
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