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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Our top choices for Chesterfield holiday rentals

Landing Downtown St. Louis

4.0 star property
8.0 out of 10, Very good, (11)
"Good place!"
Landing Downtown St. Louis

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (116)
"It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay. "
The price is AU$253
includes taxes & fees
29 Sept - 30 Sept
White House at Grand Central

Landing at Ballpark Heights - 1 Bedroom in Down...

8.8 out of 10, Excellent, (29)
"Very nice property. Location is excellent...as long as you find free parking on the street...which we did and did not have move the car for our entire stay because location is perfect! Very clean and spacious! "
Landing at Ballpark Heights - 1 Bedroom in Down...

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

9.6 out of 10, Exceptional, (45)
"Lovely stay, very sweet house in a cute neighborhood. Great for traveling with kids! Thank you!"
The price is AU$545
includes taxes & fees
11 Sept - 12 Sept
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (18)
"Walking distance to several bars and restaurants, the market, and we got front row parking. "
The price is AU$250
includes taxes & fees
1 Sept - 2 Sept
Cozy Soulard Getaway

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (74)
"The house is beautiful, in a great location, and has all the amenities of home. Definitely glad we stayed here instead of a nearby hotel."
The price is AU$577
includes taxes & fees
21 Sept - 22 Sept
Stunning 1890's Home - Sleeps 8!

Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort

10.0 out of 10, Exceptional, (63)
"Cute little house. Beautiful deck surrounded by woods and a gorgeous view of the lake. Cozy weekend get-a-way! All that we wanted. "
Cozy 2 bedroom waterfront chalet with private beach, hot tub at Innsbrook Resort

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (125)
"Thoroughly enjoyed staying here. My sister and I were in town for an event and staying here made it even more fun!"
The price is AU$267
includes taxes & fees
11 Sept - 12 Sept
Centrally located in the Tower Grove East neighborhood!

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

10.0 out of 10, Exceptional, (132)
"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

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (26)
"One night stay. Location convenient to downtown Clayton. "
The price is AU$332
includes taxes & fees
2 Sept - 3 Sept
Convenience 2 Bedroom House to Explore All of St Louis

Stylish City Reno Retreat!

7.4 out of 10, Good, (8)
"This property was not as we expected. The floor was disgustingly dirty, the dishwasher had food particles in it and smelled horrible (plus no dishwashing detergent to run a cycle), 1 roll of toilet paper, no replacement garbage bags, and opened food packages in the kitchen cabinets. I communicated these things to the owner and although he took forever to get back to me he did have someone drop off toilet paper, garbage bags, and dishwasher pods. The floor was so dirty that we needed to wear...
Stylish City Reno Retreat!

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (119)
"Everything was great!"
The price is AU$385
includes taxes & fees
29 Sept - 30 Sept
St. Charles 1860's Gem - Sleeps 6!

House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch Brewery

10.0 out of 10, Exceptional, (90)
"We enjoyed our one night stay here. There's plenty of space and lots of historic character. Everything was as described and our check in and out process was simple."
The price is AU$345
includes taxes & fees
15 Sept - 16 Sept
House in Soulard near Busch Stadium, Ballpark Village and Anheuser Busch 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!

Studio Condo on the Water @ Innsbrook

10.0 out of 10, Exceptional, (26)
"Had a good golf day wonderful place to stay "
The price is AU$284
includes taxes & fees
1 Sept - 2 Sept
Studio Condo on the Water @ Innsbrook

Modern House with Terrace Near Forest Park

9.0 out of 10, Wonderful, (11)
"This was perfect for 6. Close to a park with short running loop. Quaint shops with restaurants nearby. Would definitely stay here again!"
Modern House with Terrace Near Forest Park

Madison House 1 -Walk to Main St

9.0 out of 10, Wonderful, (11)
"Comfy fun stay!"
The price is AU$442
includes taxes & fees
11 Sept - 12 Sept
Madison House 1 -Walk to Main St

Pet-Friendly 1BR Apartment

7.6 out of 10, Good, (4)
"Awesome host. Feels like a normal home. I felt really comfortable here. "
The price is AU$238
includes taxes & fees
3 Sept - 4 Sept
Pet-Friendly 1BR Apartment

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

8.8 out of 10, Excellent, (14)
"My daughter and I were stopping on our way to Kansas and wanted to go to the Arch. Nice location to restaurants and two bedrooms. Clean and tidy place."
The price is AU$293
includes taxes & fees
11 Sept - 12 Sept
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Overlook Main St. in this 2 Bedroom Owners Suite!

4.0 star property
9.4 out of 10, Exceptional, (32)
"Perfect place for a visit to St Charles! Hope to return and stay here again!"
Overlook Main St. in this 2 Bedroom Owners Suite!
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

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$238 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 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?

Beautiful, Rehabbed Unit in Shaw Community 4228a: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Choose from 13 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.