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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Featured Cottages in Chesterfield

Quaint St Louis Home ~ 6 Mi to Downtown!
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Quaint St Louis Home ~ 6 Mi to Downtown!

3.0 star property
Quaint St Louis Home ~ 6 Mi to Downtown!
Home 2 Mi to Dtwn St Louis: Great for Families!
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Home 2 Mi to Dtwn St Louis: Great for Families!

3.0 star property
Home 2 Mi to Dtwn St Louis: Great for Families!
Pet-friendly Pacific Cottage Near Purina Farms!
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Pet-friendly Pacific Cottage Near Purina Farms!

3.0 star property
Pet-friendly Pacific Cottage Near Purina Farms!
Spacious O'fallon Vacation Home: 30 Mi to St Louis
Private kitchen

Spacious O'fallon Vacation Home: 30 Mi to St Louis

3.0 star property
Spacious O'fallon Vacation Home: 30 Mi to St Louis
St Louis Home < 1 Mi to Forest Park!
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St Louis Home < 1 Mi to Forest Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
St Louis Home < 1 Mi to Forest Park!
Historic Marthasville Getaway w/ Shared Amenities!
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Historic Marthasville Getaway w/ Shared Amenities!

3.0 star property
Historic Marthasville Getaway w/ Shared Amenities!
The Reubling House - Modern-rustic Cabin!
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The Reubling House - Modern-rustic Cabin!

3.0 star property
10.0 out of 10, Exceptional, (1)
The Reubling House - Modern-rustic Cabin!
Missouri Retreat w/ Deck, Grill & Shuffleboard!
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Missouri Retreat w/ Deck, Grill & Shuffleboard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Picked this house as it is close to the wedding venue Haue Valley. Literally a 5 min drive from there. Large beautiful home that kept all the craftsmen woodwork and charm but with modern appliances lighting etc. Roomy and comfortable furniture stocked with everything you need. Steve was very attentive to his communications. Would stay there again!! Pacific has a cute downtown with shops and restaurants within walking distance!"
Missouri Retreat w/ Deck, Grill & Shuffleboard!
St Louis Vacation Rental 4 Mi to Airport!
Private kitchen

St Louis Vacation Rental 4 Mi to Airport!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice place to stay while visiting St. Louis. My son and three grandsons joined me in for a "guy's week" and we did all the sights and saw two Cardinal's games. We cooked, grilled out and played pool and board games. we had a wonderful time and enjoyed the house very much. I would highly recommend this property whenever visiting the Gateway City !"
St Louis Vacation Rental 4 Mi to Airport!
Quiet Lakefront Cottage With Dock & Resort Access!
Terrace/patio

Quiet Lakefront Cottage With Dock & Resort Access!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This property was gorgeous and a perfect place for anyone who likes nature and it’s beauty. The owners are very kind and always available. Highly recommended. We will be back! Thank you for sharing your piece of paradise with my family. "
Quiet Lakefront Cottage With Dock & Resort Access!
9 Mi to Forest Park: Pet-friendly Home in St Louis
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9 Mi to Forest Park: Pet-friendly Home in St Louis

3.0 star property
9 Mi to Forest Park: Pet-friendly Home in St Louis
Serene Pacific Getaway: Deck, Grill & Fire Pit!
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Serene Pacific Getaway: Deck, Grill & Fire Pit!

3.0 star property
Serene Pacific Getaway: Deck, Grill & Fire Pit!
'hidden Paradise' on 5 Acres w/ Hot Tub & Deck!
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'hidden Paradise' on 5 Acres w/ Hot Tub & Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful well kept secret in a very peaceful setting: we had a large family Thanksgiving week in this beautiful place. There was more than enough rooms for four families to come together and still have enough room for dining visitors. It is beyond well equipped and you should contact the owner before you bring unnecessary items. Great hot tub. Spacious and well equipped baths and showers with all personal supplies and plush towels. Beds were all amazing. There is a great playroom...
'hidden Paradise' on 5 Acres w/ Hot Tub & Deck!
Cozy Augusta Home w/ Porch: Walk to Katy Trail!
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Cozy Augusta Home w/ Porch: Walk to Katy Trail!

3.0 star property
Cozy Augusta Home w/ Porch: Walk to Katy Trail!
Peaceful Country Home in Serene Setting With Yard
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Peaceful Country Home in Serene Setting With Yard

3.0 star property
Peaceful Country Home in Serene Setting With Yard
9 Mi to Dtwn: Vibrant St Louis Home!
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9 Mi to Dtwn: Vibrant St Louis Home!

3.0 star property
9 Mi to Dtwn: Vibrant St Louis Home!
Pet-friendly St Louis Home w/ Grill & Backyard
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Pet-friendly St Louis Home w/ Grill & Backyard

3.0 star property
10.0 out of 10, Exceptional, (1)
"Good service thank you."
Pet-friendly St Louis Home w/ Grill & Backyard
'the Cabernet Cabin' Defiance Home on Katy Trail!
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'the Cabernet Cabin' Defiance Home on Katy Trail!

3.0 star property
'the Cabernet Cabin' Defiance Home on Katy Trail!
Hillside Cabin on 43 Acres w/ Private Lake & View!
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Hillside Cabin on 43 Acres w/ Private Lake & View!

3.0 star property
Hillside Cabin on 43 Acres w/ Private Lake & View!
Dreamy St Charles Retreat w/ Furnished Patio!
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Dreamy St Charles Retreat w/ Furnished Patio!

3.0 star property
Dreamy St Charles Retreat w/ Furnished Patio!
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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Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between and 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 48 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!