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

Home in Defiance
4.96 out of 5 average rating, 49 reviewsThe Niederschulte House
Superhost

Home in Saint Charles
4.88 out of 5 average rating, 8 reviewsLuxurious couples retreat just steps from Historic
Top guest favourite

Home in Ballwin
5 out of 5 average rating, 95 reviewsPet & Child Friendly*Great Location*Ideal 4 Groups
Top guest favourite

Farm stay in Labadie
5 out of 5 average rating, 83 reviewsRomantic escape with horses you’ll never forget.
Guest favourite

Home in Des Peres
4.92 out of 5 average rating, 76 reviewsHuge yard - 10 min walk to shops & restaurants
Top guest favourite

Home in Eureka
5 out of 5 average rating, 20 reviewsGarden of Life in Eureka71, Duplex unit #1

Home in Saint Charles
4.93 out of 5 average rating, 27 reviewsRenovated 3 Bedroom Home By StayLage!
Top guest favourite

Guest house in St. Peters
4.97 out of 5 average rating, 67 reviewsMaple Tree Enchanted Guest House 1 bedroom 2 beds
Quick stats about holiday 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
Destinations to explore
- Yurt Rentals United States
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- Busch Stadium
- Six Flags St. Louis
- Saint Louis Zoo
- Central West End
- Enterprise Center
- Gateway Arch National Park
- City Museum
- Missouri Botanical Garden
- Cuivre River State Park
- St. Louis Aquarium at Union Station
- Pere Marquette State Park
- Cathedral Basilica of Saint Louis
- Meramec State Park
- The Winery at Aerie's Resort
- Castlewood State Park
- Saint Louis Science Center
- Grafton Winery the Vineyards
- Missouri History Museum
- Norwood Hills Country Club
- Raging Rivers WaterPark
- Adventure Valley Zipline Tours and Paintball Park
- Hidden Valley Ski Resort
- Boone Valley Golf Club
- Bellerive Country Club