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Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Chesterfield

White House at Grand Central
1 bedroom, individually decorated, individually furnished, desk

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
Property amenity

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
Outdoor dining

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!
Fridge, microwave, oven, stovetop

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (124)
"Perfect place to stay while we were in town for a show! "
The price is HK$973
HK$1,969 total
includes taxes & fees
12 Oct - 13 Oct
St. Charles 1860's Gem - Sleeps 6!
Residence on the Roundabout
Interior

Residence on the Roundabout

9.4 out of 10, Exceptional, (138)
"Very clean. Comfortable couch/beds"
Residence on the Roundabout
Madison House 1 -Walk to Main St
2 bedrooms, desk, iron/ironing board, travel cot

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 HK$693
HK$1,832 total
includes taxes & fees
5 Oct - 6 Oct
Madison House 1 -Walk to Main St
Centrally located in the Tower Grove East neighborhood!
Interior

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (128)
"Great stay, comfortable furnishings, quiet street. "
The price is HK$576
HK$1,304 total
includes taxes & fees
5 Oct - 6 Oct
Centrally located in the Tower Grove East neighborhood!
Convenience 2 Bedroom House to Explore All of St Louis
Fridge, microwave, stovetop, coffee/tea maker

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 HK$918
HK$2,021 total
includes taxes & fees
15 Oct - 16 Oct
Convenience 2 Bedroom House to Explore All of St Louis
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Dining

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

9.6 out of 10, Exceptional, (50)
"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 HK$1,184
HK$2,740 total
includes taxes & fees
5 Oct - 6 Oct
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Terrace/patio

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

10.0 out of 10, Exceptional, (38)
"The perfect place for our family reunion. Something for everyone….pool, basketball hoop, swing set, hot tub, fire pit and a huge yard for the kiddos to run around. "
The price is HK$3,837
HK$6,785 total
includes taxes & fees
6 Oct - 7 Oct
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Cozy Soulard Getaway
Terrace/patio

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 HK$560
HK$1,409 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Soulard Getaway
Cozy Clark Suite in Frenchtown Saint Charles
Smart TV

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
Smart TV

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 HK$763
HK$1,725 total
includes taxes & fees
7 Oct - 8 Oct
Prime Loft of Main Street
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Outdoor dining

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!
Microwave, oven, stovetop, dishwasher

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (81)
"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 HK$1,517
HK$3,134 total
includes taxes & fees
15 Oct - 16 Oct
Stunning 1890's Home - Sleeps 8!
Large Executive 1st Floor Apartment with Chefs Kitchen!
Living area

Large Executive 1st Floor Apartment with Chefs Kitchen!

9.0 out of 10, Wonderful, (16)
"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!
Serene Living Downtown STL Loft
Fridge, microwave, oven, stovetop

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 HK$455
HK$1,136 total
includes taxes & fees
16 Oct - 17 Oct
Serene Living Downtown STL Loft
Victorian Gem Steps from Main St – Sleeps 9 & Pets
Fridge, microwave, oven, stovetop

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 HK$965
HK$4,288 total
includes taxes & fees
6 Oct - 7 Oct
Victorian Gem Steps from Main St – Sleeps 9 & Pets
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
Fridge, microwave, oven, stovetop

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 HK$444
HK$1,190 total
includes taxes & fees
6 Oct - 7 Oct
Work-Ready 1BR | Fast Wi-Fi & Laundry – Steps to Tower Grove Park (65)
Entire Dogtown House near Zoo, Forest Park and Wash U
Exterior

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

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent
"Everything was clean and staff was friendly "
nichole 2-night trip
Posted 3 days ago
Drury Plaza Hotel St. Louis at the Arch

Find out more about Chesterfield

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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.