A town with a prominent church spire, residential buildings, and a hill in the background.

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

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 AU$580
includes taxes & fees
21 Oct - 22 Oct
Private 3-Acre Retreat • Koi Pond & Waterfall

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
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 AU$215
includes taxes & fees
21 Oct - 22 Oct
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

3. 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 AU$484
includes taxes & fees
20 Oct - 21 Oct
Casa de Saint Charles

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

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.6 out of 10, Exceptional, (42 reviews)
"Great spot!"
United States
Anonymous traveller
The price is AU$106
includes taxes & fees
26 Oct - 27 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

5. 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 AU$410
includes taxes & fees
8 Nov - 9 Nov
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

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)
"Nice find in the city"
United States
Mark
The price is AU$178
includes taxes & fees
25 Oct - 26 Oct
White House at Grand Central

7. 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 AU$495
includes taxes & fees
26 Oct - 27 Oct
Historic Main St. Customs House Upstairs Apartment

8. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (122 reviews)
"Great"
United States
Richard W.
The price is AU$403
includes taxes & fees
8 Nov - 9 Nov
Prime Loft of Main Street

9. 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)
"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"
United States
Chris B.
The price is AU$400
includes taxes & fees
20 Oct - 21 Oct
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

10. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (195 reviews)
"Such an awesome place! Super. Lean and great location. Loved our stay!"
United States
Jill C.
The price is AU$351
includes taxes & fees
20 Oct - 21 Oct
The Lofts of North Main Street

11. Walk to Main | Pet-Friendly Yard & Workspace

Walk to Main | Pet-Friendly Yard & Workspace
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 AU$374
includes taxes & fees
21 Oct - 22 Oct
Walk to Main | Pet-Friendly Yard & Workspace

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

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (166 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is AU$393
includes taxes & fees
20 Oct - 21 Oct
St. Charles 1860's Gem - Sleeps 6!

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 AU$374
includes taxes & fees
25 Oct - 26 Oct
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

14. Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!
Eureka
9.2 out of 10, Wonderful, (75 reviews)
"We could not believe how much space we had! It was a perfect spot for our family. We highly recommend the local dining (cafe and a pub)."
United States
Saralyn S.
The price is AU$423
includes taxes & fees
20 Oct - 21 Oct
Beautiful Villa Close to All St. Louis Attractions! Under 4 miles to Six Flags!

15. Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.0 out of 10, Wonderful, (53 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
Charming open 4bd and screen-in porch! Sleeps 10!

16. Amazing Renovated Historic Loft on Main Street

Amazing Renovated Historic Loft on Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (71 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 AU$351
includes taxes & fees
20 Oct - 21 Oct
Amazing Renovated Historic Loft on Main Street

17. Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (139 reviews)
"Super cute property, fantastic location. Very well maintained and clean, would definitely stay here again. "
United States
Jason T.
The price is AU$612
includes taxes & fees
28 Oct - 29 Oct
Stunning 1890's Home - Sleeps 8!

18. New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
St. Charles Historic District
9.6 out of 10, Exceptional, (80 reviews)
"Excellent location and neighborhood!!! House was as described and communication was great."
United States
David C.
The price is AU$967
includes taxes & fees
20 Oct - 21 Oct
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

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 AU$528
includes taxes & fees
3 Nov - 4 Nov
Adorable 2 King Bed Frenchtown Home

20. 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 AU$413
includes taxes & fees
26 Oct - 27 Oct
Cottage on Main st- Low Cleaning Fee
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

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$106 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday 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 holiday.

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 holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sophia M. Sachs Butterfly House, or you can select a more 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 are some of the best holiday rentals that Chesterfield has to offer?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Chesterfield is located in the city centre, and has a patio, a garden and a BBQ 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 holiday with amenities such as a selection of games.

How many holiday rentals are there in Chesterfield?

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

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 holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.