Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Stunning 1890's Home - Sleeps 8!

Saint Charles MO

$333 nightly

$340 total

Dec 23 - Dec 24

Total with taxes and fees

With a stay at this vacation home in St. Charles (St. Charles Historic District), you'll be within a 5-minute drive of Ameristar Casino St. Charles and Historic Main Street.

Kitchen

Washer

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

St. Louis MO

$141 nightly

$143 total

Dec 29 - Dec 30

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in St. Louis, within a 5-minute drive of Forest Park and Barnes Jewish Hospital.

Breakfast included

Kitchen

Centrally located in the Tower Grove East neighborhood!

St. Louis MO

$143 nightly

$168 total

Dec 18 - Dec 19

Total with taxes and fees

With a stay at this vacation home in St. Louis (Tower Grove East), you'll be within a 5-minute drive of St. Louis Union Station and St. Louis University.

Washer

Dryer

Home Near Main Street-Covered Patio-Hot Tub!

Saint Charles MO

$443 nightly

$452 total

Dec 18 - Dec 19

Total with taxes and fees

With a stay at this vacation home in St. Charles, you'll be within a 10-minute drive of Ameristar Casino St. Charles and Frenchtown Heritage Museum.

Hot Tub

Kitchen

Entire 4BR Home near Lafayette Square

St. Louis MO

$287 nightly

$298 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this vacation home in St. Louis (The Gate), you'll be within a 5-minute drive of St. Louis Union Station and St. Louis University.

Kitchen

Washer

Honky Tonk Hideaway

Saint Charles MO

$288 nightly

$294 total

Dec 18 - Dec 19

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in St. Charles, within a 5-minute drive of Ameristar Casino St. Charles and Historic Main Street.

Kitchen

Pet friendly

Artsy Creative Haven Home St. Louis Art District

St. Louis MO

Located in St. Louis (Grand Center), this vacation home is within a 15-minute walk of Fox Theater and St. Louis University.

Kitchen

Washer

Tamm Ave 3-BR Retreat

St. Louis MO

With a stay at this vacation home in St. Louis (Dogtown), you'll be within a 5-minute drive of Forest Park and Barnes Jewish Hospital.

Kitchen

Washer

Entire Dogtown House near Zoo, Forest Park and Wash U

St. Louis MO

With a stay at this vacation home, you'll be centrally located in St. Louis, within a 5-minute drive of Forest Park and Washington University in St. Louis.

Kitchen

Washer

Escape the city to quiet and picturesque Golden Eagle, IL..

Golden Eagle IL

This family-friendly vacation home is 3.3 mi (5.3 km) from Mississippi River and 16.8 mi (27 km) from Ameristar Casino St. Charles.

Hot Tub

Kitchen

Urban Oasis in the Heart of St. Louis

St. Louis MO

With a stay at this vacation home in St. Louis (Carondelet), you'll be a 1-minute drive from Mississippi River and 8 minutes from Busch Stadium.

Washer

Dryer

Historic luxury retreat

St Louis MO

With a stay at this vacation home in St. Louis (Lafayette Square), you'll be within a 5-minute drive of St. Louis Union Station and Gateway Arch.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.