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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chesterfield vacation homes

A spacious living area with a high ceiling, wooden beams, a fireplace, a dining area, and a cozy seating arrangement.

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Private 3-Acre Retreat • Koi Pond & Waterfall
Wildwood
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning home! Beautiful, love the koy pond!"
United States
Bailey G.
The price is CA $291
CA $572 total
includes taxes & fees
Oct 26 - Oct 27
Private 3-Acre Retreat • Koi Pond & Waterfall
A modern kitchen with a stainless steel refrigerator, an island with pink stools, a gas stove, and a large window.

2. Completely Renovated Home in St. Charles, Missouri

Completely Renovated Home in St. Charles, Missouri
Saint Charles
10.0 out of 10, Exceptional, (1 review)
"Close proximity to our job site. Quiet neighborhood."
United States
Herbert L.
The price is CA $189
CA $623 total
includes taxes & fees
Oct 26 - Oct 27
Completely Renovated Home in St. Charles, Missouri
A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

3. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (20 reviews)
"What a great place to stay! Clean, well stocked, and very spacious. Would definitely book again."
United States
Lynn D.
The price is CA $133
CA $410 total
includes taxes & fees
Oct 28 - Oct 29
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
A spacious living room with a fireplace, a ceiling fan, and a large window with shutters.

4. Saint Charles White House

Saint Charles White House
Saint Charles
8.6 out of 10, Excellent, (7 reviews)
"The host was a pleasure to work with and easy to talk to. "
United States
Matthew M.
The price is CA $179
CA $463 total
includes taxes & fees
Oct 25 - Oct 26
Saint Charles White House
A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

5. Casa de Saint Charles

Casa de Saint Charles
Saint Charles
9.2 out of 10, Wonderful, (22 reviews)
"Everything was very nice and beautiful and perfectly set up for us will book again"
United States
Xavier H.
The price is CA $179
CA $454 total
includes taxes & fees
Oct 25 - Oct 26
Casa de Saint Charles
Exterior

6. Unique Victorian Experience Near Everything

Unique Victorian Experience Near Everything
Ballwin
8.8 out of 10, Excellent, (9 reviews)
"We are happy ti share that our stay at this lovely place went very well. The location was perfect, the roominess of the property was quite pleasing."
United Kingdom
kbebault
The price is CA $315
CA $727 total
includes taxes & fees
Oct 25 - Oct 26
Unique Victorian Experience Near Everything
A modern kitchen with white cabinetry, a stainless steel range, and a built-in oven.

7. The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays

The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays
Saint Charles
9.2 out of 10, Wonderful, (5 reviews)
"We loved our stay in this cute little chalet! Location was great! We loved the privacy! Had everything we needed. Commutation was great, had everything we needed. I would recommend to anyone. We definitely would stay again!!!"
United States
KELLY S.
The price is CA $329
CA $959 total
includes taxes & fees
Oct 25 - Oct 26
The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays
A modern kitchen with white cabinets, a black refrigerator, and a central island.

8. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee
St. Charles Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Good location. Decorated very nicely. "
United States
Debbie A.
The price is CA $151
CA $400 total
includes taxes & fees
Oct 26 - Oct 27
Cottage on Main st- Low Cleaning Fee
A dining area with a wooden table, chairs, a hanging light fixture, a brick wall, and a window with a view of greenery.

9. St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (168 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is CA $221
CA $466 total
includes taxes & fees
Nov 1 - Nov 2
St. Charles 1860's Gem - Sleeps 6!
A modern living room with a fireplace, two armchairs, a small table, and decorative plants.

10. The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays

The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays
Saint Charles
9.8 out of 10, Exceptional, (8 reviews)
"Great place for a family to stay. We had our family of 5 and two others for a long weekend and really enjoyed the house. Very responsive owners and every detail in terms of things you will need like lotions and soaps and towels. Games are really fun too. Totally recommend this place."
United States
Michelle R.
The price is CA $736
CA $1,550 total
includes taxes & fees
Oct 27 - Oct 28
The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays
A room with a bed, a gray sofa, a chair, and a rug.

11. Historic 5th Street House - Fully Rehabbed # 2

Historic 5th Street House - Fully Rehabbed # 2
St. Charles Historic District
8.4 out of 10, Very good, (19 reviews)
"Wonderful place to stay would definitely recommend "
United States
Steven S.
The price is CA $139
CA $353 total
includes taxes & fees
Oct 25 - Oct 26
Historic 5th Street House - Fully Rehabbed # 2
An outdoor seating area with string lights, a Westport Social sign, and a television screen.

12. Near Westport Hub w/ Game Room & Huge Fenced Yard

Near Westport Hub w/ Game Room & Huge Fenced Yard
Old Maryland Heights
The price is CA $259
CA $640 total
includes taxes & fees
Oct 27 - Oct 28
Near Westport Hub w/ Game Room & Huge Fenced Yard
A modern kitchen with white cabinetry, stainless steel appliances, a large island with stools, pendant lighting, and a view of the outdoors.

13. The Stadium by Mercer Stays | Private 2.2Acre Sports Estate for Teams & Families

The Stadium by Mercer Stays | Private 2.2Acre Sports Estate for Teams & Families
Saint Charles
9.0 out of 10, Wonderful, (2 reviews)
"Property was good, enjoyed it"
United States
Adriane B.
The price is CA $830
CA $1,899 total
includes taxes & fees
Oct 27 - Oct 28
The Stadium by Mercer Stays | Private 2.2Acre Sports Estate for Teams & Families
A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

14. Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
St. Charles Historic District
9.6 out of 10, Exceptional, (87 reviews)
"Quaint and quiet, with easy access to downtown St Charles."
United States
Jeffrey E.
The price is CA $167
CA $349 total
includes taxes & fees
Oct 25 - Oct 26
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
A living room with a sofa, coffee table, TV, and a mirror.

15. Olivette Bungalow, 3bd 1 bth, Small Dog Friendly - Stay Smiley Rentals

Olivette Bungalow, 3bd 1 bth, Small Dog Friendly - Stay Smiley Rentals
Olivette
The price is CA $163
CA $364 total
includes taxes & fees
Oct 27 - Oct 28
Olivette Bungalow, 3bd 1 bth, Small Dog Friendly - Stay Smiley Rentals
A modern bathroom with a shower enclosure, a toilet, and a window with a view.

16. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (54 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is CA $165
CA $375 total
includes taxes & fees
Oct 25 - Oct 26
Convenience 2 Bedroom House to Explore All of St Louis
A kitchen with wooden cabinets, a microwave, an oven, a dishwasher, and a ceiling fan.

17. Historic STL Home near Clayton/Massive Backyard

Historic STL Home near Clayton/Massive Backyard
University City
The price is CA $134
CA $431 total
includes taxes & fees
Oct 25 - Oct 26
Historic STL Home near Clayton/Massive Backyard
A living room with a flat-screen TV, a sofa with patterned cushions, a coffee table, and a rug.

18. Cottage on Historic Main Street- Low Cleaning fee

Cottage on Historic Main Street- Low Cleaning fee
St. Charles Historic District
10.0 out of 10, Exceptional, (24 reviews)
"Great location to Main Street. "
United States
Daneen H.
The price is CA $186
CA $440 total
includes taxes & fees
Oct 27 - Oct 28
Cottage on Historic Main Street- Low Cleaning fee
A modern apartment with a living room, kitchen, and dining area.

19. Adorable 2 King Bed Frenchtown Home

Adorable 2 King Bed Frenchtown Home
Saint Charles
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Pet friendly. Perfect space for my wife and I to work remotely. So many great local places in close proximity. Host was quick to answer any and all questions. Would absolutely book again."
United States
Don S.
The price is CA $143
CA $512 total
includes taxes & fees
Nov 9 - Nov 10
Adorable 2 King Bed Frenchtown Home
A bar area with a wooden bar and two stools, a ceiling fan, and a window with blinds.

20. The Olive House - Near Main Street- Fully rehabbed

The Olive House - Near Main Street- Fully rehabbed
Saint Charles
8.6 out of 10, Excellent, (13 reviews)
"This was the perfect place to stay and the property was great"
United States
Stephen L.
The price is CA $175
CA $488 total
includes taxes & fees
Oct 26 - Oct 27
The Olive House - Near Main Street- Fully rehabbed
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

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

10/10 Excellent
"Our first time staying here, very near the airport but it won’t be the last. Solid facility and great staff with 24/7 shuttle service."
Murray 1-night trip
Posted 2 hours ago
Pear Tree Inn St. Louis Airport

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews
442
Accommodation
658 Vacation Homes
Lowest Price
CA $349
Highest Price
CA $1,899

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