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Chesterfield Vacation Rentals

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Sep 25 - Sep 26
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Sep 26 - Sep 27
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Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Chesterfield

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

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (118)
"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, (121)
"Perfect place to stay while we were in town for a show! "
The price is ￥18,451
￥37,788 total
includes taxes & fees
Sep 28 - Sep 29
St. Charles 1860's Gem - Sleeps 6!
Centrally located in the Tower Grove East neighborhood!
Interior

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (127)
"Great stay, comfortable furnishings, quiet street. "
The price is ￥11,013
￥24,943 total
includes taxes & fees
Sep 29 - Sep 30
Centrally located in the Tower Grove East neighborhood!
Residence on the Roundabout
Interior

Residence on the Roundabout

9.6 out of 10, Exceptional, (137)
"Very clean. Comfortable couch/beds"
Residence on the Roundabout
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)
"Home was very nice, had a great location and manager was fantastic to work with. "
The price is ￥73,517
￥128,259 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Sunrise, Rural, close to town, near wineries, next to Sunset Bluffs!
Madison House 1 -Walk to Main St
2 bedrooms, desk, iron/ironing board, travel crib

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 ￥13,137
￥34,904 total
includes taxes & fees
Sep 28 - Sep 29
Madison House 1 -Walk to Main St
Honky Tonk Hideaway
Outdoor dining

Honky Tonk Hideaway

9.2 out of 10, Wonderful, (7)
"Great place to stay"
Honky Tonk Hideaway
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 ￥17,138
￥36,775 total
includes taxes & fees
Sep 29 - Sep 30
Prime Loft of Main Street
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
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, (207)
"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!
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 ￥10,628
￥26,717 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Soulard Getaway
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, (30)
"One night stay. Location convenient to downtown Clayton. "
The price is ￥17,418
￥38,777 total
includes taxes & fees
Sep 28 - Sep 29
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, (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 ￥18,466
￥47,840 total
includes taxes & fees
Sep 28 - Sep 29
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Stunning 1890's Home - Sleeps 8!
Microwave, oven, stovetop, dishwasher

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (78)
"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 ￥29,020
￥60,086 total
includes taxes & fees
Oct 12 - Oct 13
Stunning 1890's Home - Sleeps 8!
Spacious 3BR w/ Private Yard | Steps to Soulard Market & AB Brewery
Fridge, microwave, oven, stovetop

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
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
3 bedrooms, WiFi, bed sheets

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

9.6 out of 10, Exceptional, (66)
"Comfy beds, plenty of towels, good location."
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.
Smart TV

Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

10.0 out of 10, Exceptional, (39)
"The house was very cute and cozy. The host was very responsive and even let us check n a little early. We would definitely stay here again."
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.
South City Historic Home w/ private carport
Property grounds

South City Historic Home w/ private carport

8.8 out of 10, Excellent, (43)
"Loved it nice house"
South City Historic Home w/ private carport
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

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

10/10 Excellent
"For a pretty good price it was a very nice stay, no bad smells motels have come to be known for."
Shane 1-night trip
Posted 10 hours ago
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sky Zone Indoor Trampoline Park - St. Louis, or you can go with a 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's the top vacation rental that Chesterfield has to offer?

St. Charles 1860's Gem - Sleeps 6!: Visitors like this Chesterfield vacation home rental. It 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 vacation rentals are there in Chesterfield?

Choose from 4 Expedia vacation rentals in Chesterfield for a memorable vacation.

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 vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can book for several days or more in Chesterfield. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.