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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 Contractors
Imperial
10.0 out of 10, Exceptional, (4)
"We had a nice stay in the area, and we were looking for a reasonably priced lodging for the whole family. There are a couple inflatable mattresses included in case additional beds are required. The full kitchen was appreciated, as was the comfortable couch. Solid proximity to other businesses and towns. The property is a little tricky to spot from afar off the side of the road, but it's easy to see once you're near it (Google maps is helpful). Overall, a good stay & I would stay here again!"
United States
Zach L.
$85 nightly
The price is $87
Dec 22 - Dec 23
Total with taxes and fees
Charming 1-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

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)
"Had a great stay. Great location, clean, friendly host. "
United States
Orrin P.
$236 nightly
The price is $252
Dec 20 - Dec 21
Total with taxes and fees
Cozy little house blocks from the Park & Fair Grounds. EV Charger equipped.

Stylish South City 2BR w/ Garage & Blazing Wi-fi

Stylish South City 2BR w/ Garage & Blazing Wi-fi
Dutchtown
9.6 out of 10, Exceptional, (50)
"Very clean and comfortable. "
United States
Michael M.
$189 nightly
The price is $203
Jan 12 - Jan 13, 2026
Total with taxes and fees
Stylish South City 2BR w/ Garage & Blazing Wi-fi

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)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
$150 nightly
The price is $153
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Adorable small house - quiet & safe - 2 BR 1 Bath

Adorable small house - quiet & safe - 2 BR 1 Bath
Imperial
9.4 out of 10, Exceptional, (13)
"Great place for a short get away"
United States
andytrower U.
$173 nightly
The price is $183
Dec 27 - Dec 28
Total with taxes and fees
Adorable small house - quiet & safe - 2 BR 1 Bath

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

Cozy 3 Bedroom/ Family Comfort & Convenient Location

Cozy 3 Bedroom/ Family Comfort & Convenient Location
2.0 star property
Wentzville
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! The home was very clean, check-in was super easy, and it was the perfect place for our family. Everything was exactly as described and we felt comfortable the entire time. Would definitely stay here again!"
United States
Tricia W.
$309 nightly
The price is $309
Dec 26 - Dec 27
Total with taxes and fees
Cozy 3 Bedroom/ Family Comfort & Convenient Location

Historic 5th Street House - Fully Rehabbed # 2

Historic 5th Street House - Fully Rehabbed # 2
St. Charles Historic District
8.8 out of 10, Excellent, (11)
"Wonderful place to stay would definitely recommend "
United States
Steven S.
$209 nightly
The price is $235
Dec 21 - Dec 22
Total with taxes and fees
Historic 5th Street House - Fully Rehabbed # 2

St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends

St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends
St. Peters
9.8 out of 10, Exceptional, (7)
"Perfectly appointed property from amenities inside to lighted walk-ways outside. Excellent location (for us) to family, friends, and the highway! Very serene area and felt totally safe at all times - even walking to the car at night by myself. "
United States
Lisa & Fred W.
$241 nightly
The price is $274
Jan 12 - Jan 13, 2026
Total with taxes and fees
St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends

Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (136)
"Great little place and location was close to our event."
United States
RL T.
$138 nightly
The price is $162
Dec 21 - Dec 22
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!

Stylish 2BR/2BA House in The Grove w/ Free Parking

Stylish 2BR/2BA House in The Grove w/ Free Parking
The Grove
10.0 out of 10, Exceptional, (1)
"We really enjoyed our time in the Grove. This renovated property was clean and comfortable and the host was very happy to answer any questions. Highly recommend!"
United States
Suzanne L.
$243 nightly
The price is $265
Dec 23 - Dec 24
Total with taxes and fees
Stylish 2BR/2BA House in The Grove w/ Free Parking

Cute ranch house -quiet & safe -3 BR 1 Bath

Cute ranch house -quiet & safe -3 BR 1 Bath
Imperial
9.8 out of 10, Exceptional, (22)
"Check in was interesting but owner communicated very well. Overall, it was what we needed for our trip. "
United States
Patrick W.
$199 nightly
The price is $211
Dec 22 - Dec 23
Total with taxes and fees
Cute ranch house -quiet & safe -3 BR 1 Bath

Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (47)
"Such a charming house. Very clean with great amenities. "
United States
Darla M.
$170 nightly
The price is $191
Dec 20 - Dec 21
Total with taxes and fees
Pet and kid friendly duplex with 2 bedrooms

Delightful 2-bedroom house with AC in Berkeley Iconixx Getaway STL

Delightful 2-bedroom house with AC in Berkeley Iconixx Getaway STL
2.0 star property
Berkeley
10.0 out of 10, Exceptional, (2)
"This property was very clean, family/friends friendly, and was an overall great stay! I would stay here again if given the chance in the future! "
United States
LaKeisha W.
$257 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Delightful 2-bedroom house with AC in Berkeley Iconixx Getaway STL

Quaint and Cozy Hamlet

Quaint and Cozy Hamlet
O'Fallon
9.4 out of 10, Exceptional, (13)
"Overall great time- communication was wonderful with Kevin, neighborhood was quiet, perfect for our stay. The house wasn’t as clean as I’d expect but besides that, great stay!"
United States
Madison A.
$342 nightly
The price is $351
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint and Cozy Hamlet

1st Capitol Mansion - Suite 401

1st Capitol Mansion - Suite 401
St. Charles Historic District
8.4 out of 10, Very Good, (7)
"Nice property and a great location to all the shops and restaurants that St. Charles has to offer. The place was clean and nicely updated. Will definitely stay here again!"
United States
Emily L.
$209 nightly
The price is $235
Dec 22 - Dec 23
Total with taxes and fees
1st Capitol Mansion - Suite 401

Madison House 1 -Walk to Main St

Madison House 1 -Walk to Main St
St. Charles Historic District
8.4 out of 10, Very Good, (15)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
$209 nightly
The price is $235
Dec 22 - Dec 23
Total with taxes and fees
Madison House 1 -Walk to Main St

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (39)
"Place was clean and host was accommodating."
United States
Timothy M.
$245 nightly
The price is $263
Jan 4 - Jan 5, 2026
Total with taxes and fees
Convenience 2 Bedroom House to Explore All of St Louis

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery
Soulard
10.0 out of 10, Exceptional, (98)
"Great place in a quiet neighborhood. Would definitely stay here again. "
United States
John S.
$216 nightly
The price is $228
Dec 28 - Dec 29
Total with taxes and fees
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

The Below Deck Suite

The Below Deck Suite
Saint Charles
9.0 out of 10, Wonderful, (2)
"Overall good place for a family. The neighborhood is quiet and there is a good amount of space. Easy to find and to get places. You will hear the people upstairs and one bed was very squeaky. It was very clean and the couches are very comfy. "
United States
Amy B.
$254 nightly
The price is $254
Dec 21 - Dec 22
Total with taxes and fees
The Below Deck Suite
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

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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