
Holiday rentals in Chesterfield
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
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
Superhost

Flat in Kirkwood
4.91 out of 5 average rating, 32 reviewsRate Drop! Cozy Kirkwood (2) Bedroom
Top guest favourite

Home in Saint Charles
4.93 out of 5 average rating, 57 reviewsBlair's House in St. Charles - 4 bedroom 2.5 Bath
Superhost

Home in Saint Charles
4.89 out of 5 average rating, 9 reviewsLuxurious couples retreat just steps from Historic
Guest favourite

Home in St. Louis
4.9 out of 5 average rating, 60 reviewsSpacious Villa in Historic Dogtown!
Top guest favourite

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

Home in Augusta
5 out of 5 average rating, 17 reviews"The Villa" at Villa Augusta in MO wine country
Guest favourite

Guest suite in Weldon Spring
4.94 out of 5 average rating, 49 reviewsWanderlust

Home in Saint Charles
4.93 out of 5 average rating, 27 reviewsRenovated 3 Bedroom Home By StayLage!
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
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Adventure Valley Zipline Tours and Paintball Park
- Raging Rivers WaterPark
- Norwood Hills Country Club
- Missouri History Museum
- Hidden Valley Ski Resort
- Boone Valley Golf Club
- Bellerive Country Club