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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

White House at Grand Central

4.0 star property
8.4 out of 10, Very good, (121)
"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

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 AU$367
includes taxes & fees
14 Oct - 15 Oct
Madison House 1 -Walk to Main St

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (126)
"Perfect place to stay while we were in town for a show! "
The price is AU$393
includes taxes & fees
26 Oct - 27 Oct
St. Charles 1860's Gem - Sleeps 6!

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (130)
"Great stay, comfortable furnishings, quiet street. "
The price is AU$262
includes taxes & fees
14 Oct - 15 Oct
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, (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

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 AU$207
includes taxes & fees
23 Oct - 24 Oct
Serene Living Downtown STL Loft

Cozy Clark Suite in Frenchtown Saint Charles

9.4 out of 10, Exceptional, (9)
"Perfect for a couple. Well maintained. "
Cozy Clark Suite in Frenchtown Saint Charles

Convenience 2 Bedroom House to Explore All of St Louis

9.8 out of 10, Exceptional, (34)
"One night stay. Location convenient to downtown Clayton. "
The price is AU$412
includes taxes & fees
14 Oct - 15 Oct
Convenience 2 Bedroom House to Explore All of St Louis

Studio Condo on the Water @ Innsbrook

9.8 out of 10, Exceptional, (34)
"Had a good golf day wonderful place to stay "
The price is AU$285
includes taxes & fees
20 Oct - 21 Oct
Studio Condo on the Water @ Innsbrook

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

10.0 out of 10, Exceptional, (209)
"Nice view of the Mississippi in the morning. Just off of the main street in old town St Charles, this place was perfect for our needs."
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Stylish City Reno Retreat!

6.4 out of 10, (10)
"The location was great for the zoo and the activities we had planned. The property was very spacious and well cleaned. Would definitely stay again!"
Stylish City Reno Retreat!

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

9.6 out of 10, Exceptional, (51)
"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 AU$524
includes taxes & fees
19 Oct - 20 Oct
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (82)
"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 AU$630
includes taxes & fees
15 Oct - 16 Oct
Stunning 1890's Home - Sleeps 8!

Authentic Log cabin with something for everyone!

9.6 out of 10, Exceptional, (373)
"We stayed here for a wedding at a venue near by. Perfect location. Peaceful atmosphere. Plenty of room. "
Authentic Log cabin with something for everyone!

Residence on the Roundabout

9.4 out of 10, Exceptional, (138)
"The house fit the purpose we needed it for. It had enough room for my family. "
Residence on the Roundabout

Cozy Soulard Getaway

9.2 out of 10, Wonderful, (27)
"Great location! Wonderful place,"
The price is AU$283
includes taxes & fees
14 Oct - 15 Oct
Cozy Soulard Getaway

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 AU$255
includes taxes & fees
14 Oct - 15 Oct
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)

Spacious 2 BR Balcony Hideaway

8.0 out of 10, Very good, (12)
"Great stay! Management was easy to reach and very helpful when we couldnt find the correct wifi network. Nice place, would stay again."
Spacious 2 BR Balcony Hideaway

Entire Dogtown House near Zoo, Forest Park and Wash U

10.0 out of 10, Exceptional, (214)
"Great place to stay. Quiet area and close to activities. "
Entire Dogtown House near Zoo, Forest Park and Wash U
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$207 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?

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.