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Our top choices for Chesterfield vacation homes

Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling ContractorsImperial
10.0 out of 10, Exceptional, (4)
$85 nightly
The price is $87
Dec 22 - Dec 23
Total with taxes and fees

Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.
Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.Washington
10.0 out of 10, Exceptional, (59)
$236 nightly
The price is $252
Dec 20 - Dec 21
Total with taxes and fees

Stylish South City 2BR w/ Garage & Blazing Wi-fi
Stylish South City 2BR w/ Garage & Blazing Wi-fiDutchtown
9.6 out of 10, Exceptional, (50)
$189 nightly
The price is $203
Jan 12 - Jan 13, 2026
Total with taxes and fees

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!The Hill
9.8 out of 10, Exceptional, (160)
$150 nightly
The price is $153
Jan 4 - Jan 5, 2026
Total with taxes and fees

Adorable small house - quiet & safe - 2 BR 1 Bath
Adorable small house - quiet & safe - 2 BR 1 BathImperial
9.4 out of 10, Exceptional, (13)
$173 nightly
The price is $183
Dec 27 - Dec 28
Total with taxes and fees

2 bed 1 bath full kitchen house just a mile away from airport.. ask me anything
2 bed 1 bath full kitchen house just a mile away from airport.. ask me anythingWoodson Terrace
$209 nightly
The price is $209
Dec 21 - Dec 22
Total with taxes and fees

Cozy 3 Bedroom/ Family Comfort & Convenient Location
Cozy 3 Bedroom/ Family Comfort & Convenient LocationWentzville
10.0 out of 10, Exceptional, (1)
$309 nightly
The price is $309
Dec 26 - Dec 27
Total with taxes and fees

Historic 5th Street House - Fully Rehabbed # 2
Historic 5th Street House - Fully Rehabbed # 2St. Charles Historic District
8.8 out of 10, Excellent, (11)
$209 nightly
The price is $235
Dec 21 - Dec 22
Total with taxes and fees
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.
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Top Chesterfield Hotel Reviews

Drury Plaza Hotel St. Louis at the Arch
10/10 Excellent
Find out more about Chesterfield
Chesterfield Vacation Homes information
Number of reviews | 1 |
|---|---|
Accommodation | 634 Vacation Homes |
Lowest Price | $417 |
Highest Price | $417 |
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