
Vacation rentals in Chesterfield
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Top-rated vacation rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterfield vacation rentals
Other great vacation rentals in Chesterfield

Cozy Hilltop Cottage
Basement is really cool

Home away from Home St. Louis Cnty Ladue Schools
the place was great and was in the perfect location for us. Lisa was so nice, and we felt very comfortable. I would recommend staying here to anyone.

Big Lake 'Livin A-Frame Chalet in Innsbrook Resort
My family and I used this location for spring break and we had a blast. We were able to light a fire, use the boats, and jacuzzi. The place was very clean. Any issues (which was very few) were addressed imediately. Thank you so much for allowing us the opportunity to stay at your beautiful cabin

Bright Urban Comfort | JZ Vacation Rentals
This house was perfect for a larger group! We felt like we had a lot of space even with 12 people in the house! The location was perfect, as it only took 7-9 minutes to get to most tourist attractions. We appreciated how clean the house was as well! The house is exactly as it shows in the pictures! We would definitely stay here again on our next trip!

Pelican's Perch
Fantastic host. Beautiful property.

Quaint and Cozy Hamlet
place was squeaky clean and host was responsive to any questions. would stay at this location again!

Waterside Cottage w/ Hot Tub by StayLage
Beautiful little cabin set back in a very private setting. Made for a perfect end of summer getaway

Cozy Cottage off Main Street in Grafton
The cottage was perfect for our weekend getaway! Linda was responsive, kind, and helpful. The space was clean and cozy. Highly recommend if you want a cute space close to the fun shops and restaurants in Grafton!
Quick stats about vacation rentals in Chesterfield
Total rentals
40 properties
Total number of reviews
400 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Frequently Asked Questions
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Chesterfield?
Experience the best of Chesterfield with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 20 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Busch Stadium
- Enterprise Center
- Six Flags St. Louis
- Saint Louis Zoo
- Central West End
- Gateway Arch National Park
- Missouri Botanical Garden
- St. Louis Aquarium at Union Station
- City Museum
- Saint Louis Science Center
- Hidden Valley Ski Resort
- Castlewood State Park
- Meramec State Park
- Pere Marquette State Park
- Missouri History Museum
- Grafton Winery the Vineyards
- St. Louis Country Club
- Cuivre River State Park
- Adventure Valley Zipline Tours and Paintball Park
- Cathedral Basilica of Saint Louis
- The Winery at Aerie's Resort
- Raging Rivers WaterPark
- Boone Valley Golf Club
- Norwood Hills Country Club
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