Photo by Michelle E

Chesterfield Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Chesterfield

White House at Grand Central

4.0 star property
8.4 out of 10, Very good, (120)
"The property is in a Safe neighborhood. "
White House at Grand Central

Landing Downtown St. Louis

4.0 star property
7.6 out of 10, Good, (15)
"Great place to stay when watching the Cardinals. "
Landing Downtown St. Louis

The St. Charles Guest House, lovely historic home, fun for families and groups

10.0 out of 10, Exceptional, (133)
"We loved staying here in this adorable clean house that was only 1 block off of downtown Main Street shopping. "
The St. Charles Guest House, lovely historic home, fun for families and groups

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (122)
"Perfect place to stay while we were in town for a show! "
The price is NZ$440
includes taxes & fees
30 Sept - 1 Oct
St. Charles 1860's Gem - Sleeps 6!

Residence on the Roundabout

9.4 out of 10, Exceptional, (138)
"Very clean. Comfortable couch/beds"
Residence on the Roundabout

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (128)
"Great stay, comfortable furnishings, quiet street. "
The price is NZ$290
includes taxes & fees
30 Sept - 1 Oct
Centrally located in the Tower Grove East neighborhood!

Madison House 1 -Walk to Main St

8.8 out of 10, Excellent, (13)
"Comfortable place to stay easy to find location close to everything in St Charles"
The price is NZ$408
includes taxes & fees
30 Sept - 1 Oct
Madison House 1 -Walk to Main St

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (31)
"One night stay. Location convenient to downtown Clayton. "
The price is NZ$459
includes taxes & fees
30 Sept - 1 Oct
Convenience 2 Bedroom House to Explore All of St Louis

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

9.6 out of 10, Exceptional, (49)
"This place was perfect for our visit to St Charles. We'll definitely book it again the next time we come to visit family"
The price is NZ$541
includes taxes & fees
30 Sept - 1 Oct
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (25)
"We really enjoyed this location and property. Can’t wait to come back."
The price is NZ$317
includes taxes & fees
1 Oct - 2 Oct
Cozy Soulard Getaway

Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

10.0 out of 10, Exceptional, (38)
"Home was very nice, had a great location and manager was fantastic to work with. "
The price is NZ$1,493
includes taxes & fees
6 Oct - 7 Oct
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!

Cozy Clark Suite in Frenchtown Saint Charles

9.4 out of 10, Exceptional, (8)
"Perfect for a couple. Well maintained. "
Cozy Clark Suite in Frenchtown Saint Charles

Prime Loft of Main Street

9.8 out of 10, Exceptional, (99)
"This is a great property located in wiyhin walking distance to shops restaurants and interesting things to see"
The price is NZ$384
includes taxes & fees
30 Sept - 1 Oct
Prime Loft of Main Street

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (208)
"The riverside guest house was a perfect find for our two day getaway. Would definitely stay again. Perfect location. "
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (79)
"We loved this beautiful property. The host was great at communicating with us and took care of everything we needed to accommodate my family. We will be booking this property for our next stay!"
The price is NZ$700
includes taxes & fees
12 Oct - 13 Oct
Stunning 1890's Home - Sleeps 8!

Spacious 3BR w/ Private Yard | Steps to Soulard Market & AB Brewery

10.0 out of 10, Exceptional, (17)
"Beautiful house in a great little neighborhood. We loved our stay!"
Spacious 3BR w/ Private Yard | Steps to Soulard Market & AB Brewery

Large Executive 1st Floor Apartment with Chefs Kitchen!

9.0 out of 10, Wonderful, (15)
"This place is beautiful! Comfortable bed, big kitchen. Nice living room area. Quiet and safe. We liked it a lot. "
Large Executive 1st Floor Apartment with Chefs Kitchen!

Victorian Gem Steps from Main St – Sleeps 9 & Pets

9.8 out of 10, Exceptional, (17)
"Great location and accommodation for a business trip with some colleagues. Easy to check in and find everything we needed! Super cute and cozy!"
The price is NZ$1,177
includes taxes & fees
30 Sept - 1 Oct
Victorian Gem Steps from Main St – Sleeps 9 & Pets

Serene Living Downtown STL Loft

7.6 out of 10, Good, (9)
"This loft was great. We were able to walk to restaurants, some attractions, Washington Ave.and the Metro Link. The loft was very clean and roomy. At night you can watch volleyball from the living room. The host was very responsive. I would stay here again."
The price is NZ$245
includes taxes & fees
30 Sept - 1 Oct
Serene Living Downtown STL Loft

Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)

2.0 star property
7.2 out of 10, Good, (10)
"Location was quiet and safe and apartment was as shown in pictures "
The price is NZ$265
includes taxes & fees
1 Oct - 2 Oct
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

Find out more about Chesterfield

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 favorite 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 depends 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 NZ$245 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 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 Sky Zone Indoor Trampoline Park - St. Louis, 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?

St. Charles 1860's Gem - Sleeps 6!: This holiday home rental outside of Chesterfield is located on a river, and has a garden, a selection of books and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chesterfield?

Choose from 4 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 Chesterfield Sports Fusion, 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.