
House holiday rentals in Chesterfield
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Willow Creek: Mid-Century Oasis

Private indoor pool & sauna

Clark Brick House w/ Pool | Historic St. Charles

Blair's Pool House - Creve Couer Hot Tub Game Room

Arch View Luxury Home:Pool,Sauna,Free Wine &Brkfst

Spacious Family Home w/ Pool & Amazing Spaces

Roomy Oasis with hot tub on the Hill!

Innsbrook Luxe Escape (5 bedrooms)
Weekly house rentals

Clean, 3bd/2bath home! Longer stays available!

Updated Farmhouse 2 bdrm 2 bd 2 acres

Freshly remodeled house "on The Hill"

New: Cozy Cottage Near The Hill

Luxurious Artisan Oasis.

Dogtown Century home near Forest Park & Maplewood

Updated 1913 Home in Historic Saint Charles

Top Rated | Perfect Location 3BR + Epic Game Room
Private house rentals

Charming King Bed Retreat, Great for Families!

Backyard retreat, King Bed, Historic St. Louis Gem

Luxurious, spa-like couples retreat steps from Mai

Cul De Sac - huge yard, great for families

Garden of Life in Eureka71, Duplex unit #1

American Spirit

3+ private acres, Koi fish pond, garage parking

Charming 2-Bed Brownstone in The Heart of New Town
Destinations to explore
- Chicago Holiday rentals
- Nashville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Harpeth River Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Branson Holiday rentals
- Southern Indiana Holiday rentals
- Kansas City Holiday rentals
- Lake of the Ozarks Holiday rentals
- Busch Stadium
- Six Flags St. Louis
- Central West End
- Saint Louis Zoo
- Enterprise Center
- City Museum
- Missouri Botanical Garden
- Cuivre River State Park
- St. Louis Aquarium at Union Station
- Pere Marquette State Park
- Meramec State Park
- The Winery at Aerie's Resort
- Castlewood State Park
- Grafton Winery the Vineyards
- Cathedral Basilica of Saint Louis
- Hidden Valley Ski Resort
- Norwood Hills Country Club
- Raging Rivers WaterPark
- Saint Louis Science Center
- Adventure Valley Zipline Tours and Paintball Park
- Bellerive Country Club
- Missouri History Museum
- Old Warson Country Club
- Boone Valley Golf Club