A city skyline with a prominent arch bridge and a lit bridge over a calm river reflecting city lights.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesterfield vacation rentals

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 ￥32,613
￥63,269 total
includes taxes & fees
Oct 27 - Oct 28
Private 3-Acre Retreat • Koi Pond & Waterfall
A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

2. 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 ￥20,864
￥52,167 total
includes taxes & fees
Nov 2 - Nov 3
Casa de Saint Charles
A set of stone steps leading to a garage with a car parked inside.

3. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Ballwin
7.8 out of 10, Good, (24 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
The price is ￥10,589
￥23,088 total
includes taxes & fees
Oct 27 - Oct 28
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

4. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.4 out of 10, Exceptional, (43 reviews)
"Great spot!"
United States
Anonymous traveler
The price is ￥9,294
￥10,781 total
includes taxes & fees
Oct 29 - Oct 30
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A residential building with a patio area featuring outdoor furniture and string lights.

5. 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 ￥14,934
￥45,806 total
includes taxes & fees
Oct 27 - Oct 28
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
A spacious foyer with a grand staircase, a piano, and a large rug.

6. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.4 out of 10, Very good, (167 reviews)
"Very spacious clean old house apartments"
United States
Priscilla
The price is ￥11,935
￥19,446 total
includes taxes & fees
Oct 27 - Oct 28
White House at Grand Central
A modern kitchen with white cabinets, a black refrigerator, and a central island.

7. 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 ￥17,726
￥45,638 total
includes taxes & fees
Nov 3 - Nov 4
Cottage on Main st- Low Cleaning Fee
Clubhouse

8. Serene Seebach Sights by Innsbrook Vacations!

Serene Seebach Sights by Innsbrook Vacations!
Innsbrook
9.6 out of 10, Exceptional, (15 reviews)
"Great clubhouse, plenty of wildlife roaming grounds, and friendly atmosphere."
United States
tony
The price is ￥14,404
￥39,003 total
includes taxes & fees
Oct 27 - Oct 28
Serene Seebach Sights by Innsbrook Vacations!
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

9. Historic Main St. Customs House Upstairs Apartment

Historic Main St. Customs House Upstairs Apartment
St. Charles Historic District
9.6 out of 10, Exceptional, (39 reviews)
"Lovely place to stay!"
United States
Margaret A.
The price is ￥19,483
￥56,297 total
includes taxes & fees
Oct 29 - Oct 30
Historic Main St. Customs House Upstairs Apartment
A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

10. 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 ￥18,668
￥38,939 total
includes taxes & fees
Oct 27 - Oct 28
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
A spacious living area with a wooden floor, a dining table with chairs, a flat-screen TV mounted on the wall, and a kitchen area with modern appliances.

11. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (196 reviews)
"Such an awesome place! Super. Lean and great location. Loved our stay!"
United States
Jill C.
The price is ￥17,444
￥38,149 total
includes taxes & fees
Oct 28 - Oct 29
The Lofts of North Main Street
An outdoor hot tub area with seating and a covered patio.

12. Private Basement - Two King Beds and Hot Tub

Private Basement - Two King Beds and Hot Tub
Saint Charles
9.6 out of 10, Exceptional, (5 reviews)
"This property is the perfect get-away. Quite relaxing. The beds are super comfy the outside sitting area is quiet and relaxing. The interior is fully furnished very nice quality everything. And you are within 10 minutes of shopping and tons of restaurants. I hated to leave.Hope I can return."
United States
JoAnn C.
The price is ￥13,334
￥53,543 total
includes taxes & fees
Oct 28 - Oct 29
Private Basement - Two King Beds and Hot Tub
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

13. 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, (55 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is ￥18,511
￥41,579 total
includes taxes & fees
Oct 27 - Oct 28
Convenience 2 Bedroom House to Explore All of St Louis
A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

14. Dog-Friendly Studio on Historic Main Street

Dog-Friendly Studio on Historic Main Street
St. Charles Historic District
9.2 out of 10, Wonderful, (40 reviews)
"Had a wonderful stay. It was a Monday night so parking was very easy and the room was clean and comfortable. I would recommend this place 100% "
United States
Sarah C.
The price is ￥14,401
￥35,415 total
includes taxes & fees
Oct 29 - Oct 30
Dog-Friendly Studio on Historic Main Street
A spacious living room with a green sofa, a purple armchair, a wooden staircase, and a ceiling fan.

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

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.6 out of 10, Exceptional, (170 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is ￥24,785
￥51,720 total
includes taxes & fees
Oct 27 - Oct 28
St. Charles 1860's Gem - Sleeps 6!
A living room with a green sofa, a wooden coffee table, and hanging plants.

16. Safe and private apt-Near Forest Park-Free parking

Safe and private apt-Near Forest Park-Free parking
Dogtown
7.6 out of 10, Good, (17 reviews)
"I loved that it was in an older building and there is history there. The best were comfortable, and the apartment was spotless."
United States
Machelle
The price is ￥7,844
￥26,512 total
includes taxes & fees
Oct 27 - Oct 28
Safe and private apt-Near Forest Park-Free parking
A staircase with white railings and a ceiling fan.

17. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (72 reviews)
"This was a prime spot for downtown activities! Near everything and not far from STL. Would absolutely stay here again!"
United States
Rebecca F.
The price is ￥17,444
￥38,149 total
includes taxes & fees
Oct 27 - Oct 28
Amazing Renovated Historic Loft on Main Street
Free breakfast available on-site.

18. Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Westport
9.8 out of 10, Exceptional, (6 reviews)
"Everything from the staff to the amenities to the rooms were amazing! Definitely recommend staying here! "
Canada
Lashon C.
The price is ￥35,068
￥45,696 total
includes taxes & fees
Nov 15 - Nov 16
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

19. Home Near Main with Pet-Friendly Yard and Office

Home Near Main with Pet-Friendly Yard and Office
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
The price is ￥19,954
￥45,696 total
includes taxes & fees
Nov 8 - Nov 9
Home Near Main with Pet-Friendly Yard and Office
A modern apartment with a living room, kitchen, and dining area.

20. 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 ￥15,687
￥56,528 total
includes taxes & fees
Oct 27 - Oct 28
Adorable 2 King Bed Frenchtown Home
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
"It was excellent staff front desk"
Jim 1-night trip
Posted 1 hour ago
Pear Tree Inn St. Louis Airport

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sophia M. Sachs Butterfly House, or you can go with a secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What's the top vacation rental that Chesterfield has to offer?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: Visitors like this Chesterfield vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chesterfield?

Choose from 8 Expedia vacation rentals in Chesterfield for a memorable vacation.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. Other places in town to visit include The Factory and St. Louis Premium Outlets.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can book for several days or more in Chesterfield. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.