Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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)
"Our host was incredibly accommodating and went above and beyond to make sure we had everything we needed throughout our stay. The property was beautiful, exceptionally clean, and offered the perfect amount of privacy.We truly can't say enough about how much we enjoyed our stay. It exceeded our expectations in every way. Whenever we return to St. Louis, this will absolutely be our first choice. We look forward to staying here again!"
United States
Robin H.
The price is CA $255
CA $503 total
includes taxes & fees
Nov 9 - Nov 10
Private 3-Acre Retreat • Koi Pond & Waterfall
A set of stone steps leading to a garage with a car parked inside.

2. 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
8.0 out of 10, Very good, (25 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
The price is CA $95
CA $195 total
includes taxes & fees
Nov 9 - Nov 10
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A hotel lobby with a staircase, a reception desk, and a seating area.

3. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

2 Queen Beds | Mobil Access Tub Nsmk Kitchen
Westport
9.6 out of 10, Exceptional, (46 reviews)
"Great place to stay!"
United States
Anonymous traveller
The price is CA $79
CA $91 total
includes taxes & fees
Nov 24 - Nov 25
2 Queen Beds | Mobil Access Tub Nsmk Kitchen
A residential building with a patio area featuring outdoor furniture and string lights.

4. 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, (21 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 $392 total
includes taxes & fees
Nov 16 - Nov 17
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
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 $184
CA $442 total
includes taxes & fees
Nov 9 - Nov 10
Casa de Saint Charles
An outdoor hot tub area with seating and a covered patio.

6. 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)
"Clean. The patio was very comfortable and nice to sit and relax. The beds were also very comfortable."
United States
Beth S.
The price is CA $119
CA $459 total
includes taxes & fees
Nov 8 - Nov 9
Private Basement - Two King Beds and Hot Tub
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.

7. 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, (13 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 CA $160
CA $368 total
includes taxes & fees
Nov 8 - Nov 9
Home Near Main with Pet-Friendly Yard and Office
A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

8. 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 CA $129
CA $302 total
includes taxes & fees
Nov 9 - Nov 10
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.

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, (171 reviews)
"Perfect home, fantastic stay. Thank you so much. We hope to visit again!"
United States
Jackie D.
The price is CA $221
CA $426 total
includes taxes & fees
Dec 7 - Dec 8
St. Charles 1860's Gem - Sleeps 6!
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

10. 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 traveller
The price is CA $78
CA $90 total
includes taxes & fees
Nov 10 - Nov 11
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

11. 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 CA $174
CA $485 total
includes taxes & fees
Nov 9 - Nov 10
Historic Main St. Customs House Upstairs Apartment
A bedroom with a bed, bedside table, and a large painting on the wall.

12. 6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (25 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
6649 1E | Garden Style Studio Near Forest Park
A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

13. 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 $334 total
includes taxes & fees
Nov 9 - Nov 10
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

14. Spacious, 3 bedroom home, finished basement on quiet court

Spacious, 3 bedroom home, finished basement on quiet court
St. Peters
9.8 out of 10, Exceptional, (58 reviews)
"Great place"
United States
ed n.
The price is CA $189
CA $582 total
includes taxes & fees
Nov 8 - Nov 9
Spacious, 3 bedroom home, finished basement on quiet court
A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

15. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (123 reviews)
"Great"
United States
Richard W.
The price is CA $194
CA $358 total
includes taxes & fees
Dec 7 - Dec 8
Prime Loft of Main Street
A spacious foyer with a grand staircase, a piano, and a large rug.

16. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.2 out of 10, Very good, (168 reviews)
"Very spacious clean old house apartments"
United States
Priscilla
The price is CA $107
CA $174 total
includes taxes & fees
Nov 8 - Nov 9
White House at Grand Central
A modern kitchen with white cabinets, a black refrigerator, and a central island.

17. 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 $161
CA $393 total
includes taxes & fees
Nov 16 - Nov 17
Cottage on Main st- Low Cleaning Fee
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.

18. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (196 reviews)
"Very cute place, walking distance to everything."
United States
Liberty A.
The price is CA $194
CA $358 total
includes taxes & fees
Dec 7 - Dec 8
The Lofts of North Main Street
A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

19. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"Hot water was an issue. Other than that great place to stay"
United States
Ashley C.
The price is CA $112
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
6653 2S | Jewel of Central St. Louis
Property grounds

20. Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
Imperial
9.8 out of 10, Exceptional, (8 reviews)
"Thank you we enjoyed the place but we would like to get some more nights if all possible"
United States
Tommy H.
The price is CA $107
CA $155 total
includes taxes & fees
Nov 8 - Nov 9
Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors
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.
View all properties

Find vacation rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Top Chesterfield Hotel Reviews

A modern kitchen with a bar area, wooden cabinets, and pendant lighting.
Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield
Chesterfield

10/10 Excellent

Great place
Canada
Cedric
Reviewed August 31, 2025
Hyatt Place St. Louis/Chesterfield

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.