A town with a prominent church spire, residential buildings, and a hill in the background.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chesterfield cottages

Exterior

The Blake Cottage Wine Country Home

The Blake Cottage Wine Country Home
Augusta
8.4 out of 10, Very Good, (11 reviews)
"It was a wonderful location for our girls' night! Plenty of room for our group and within walking distance of the wineries. "
United States
Deana T.
$376 nightly
The price is $419
Jul 13 - Jul 14
Total with taxes and fees
The Blake Cottage Wine Country Home
Exterior

Hound Haus - Dog Friendly, near Purina Farms and WashMO

Hound Haus - Dog Friendly, near Purina Farms and WashMO
Villa Ridge
9.8 out of 10, Exceptional, (35 reviews)
"Super cozy and peaceful "
United States
Gracia
$269 nightly
The price is $285
Jul 12 - Jul 13
Total with taxes and fees
Hound Haus - Dog Friendly, near Purina Farms and WashMO
Interior

3323: Uptown Elegant Escape by JZ Vacation Rentals

3323: Uptown Elegant Escape by JZ Vacation Rentals
2.0 star property
The Gate
$923 nightly
The price is $1,079
Jul 26 - Jul 27
Total with taxes and fees
3323: Uptown Elegant Escape by JZ Vacation Rentals
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

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

10/10 Excellent
"First time staying at a Hyatt, we definitely enjoyed ourselves."
Russell 2-night trip
Posted 3 hours ago
Hyatt Regency St. Louis at The Arch

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
46
Accommodation
73 Cottages
Lowest Price
$285
Highest Price
$1,079

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between $285 and $1,079 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chesterfield?
Enjoy nature's beauty in one of the 73 cottages waiting for you in Chesterfield. To help you choose a place that's right for you, take advantage of our filters to search for must-have perks or amenities.
Why book your cottage in Chesterfield with Expedia?
Reserving a cottage in Chesterfield is as simple as clicking on your travel dates and selecting your ideal place for outdoor fun and relaxation. From luxurious retreats to low-cost stays and cottages that offer amenities like laundry facilities, Expedia has something for all styles and tastes. As for unbeatable deals? We've have them as well!
How can I find cheap cottages in Chesterfield?
With Expedia's helpful filter tool, comparing cheap cottages in Chesterfield has never been simpler. To discover accommodations that'll make your bank balance smile, fine-tune your search results by amenities, budget and star rating.
What is there to do in Chesterfield near my cottage?
Whatever your interests, Chesterfield has loads to keep you on the go. St. Louis Premium Outlets, The Factory and Chesterfield Sports Fusion are on most visitors' to-do lists. Don't leave without exploring Westfield Chesterfield Mall, Babler State Park and Sophia M. Sachs Butterfly House either. With Expedia's hotel deals in Chesterfield, you'll be able to see more popular attractions like these with the money you save.

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