Photo by Michelle E

Search Chesterfield Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Chesterfield

Quaint St Louis Home ~ 6 Mi to Downtown!
Interior

Quaint St Louis Home ~ 6 Mi to Downtown!

3.0 star property
Quaint St Louis Home ~ 6 Mi to Downtown!
The Reubling House - Modern-rustic Cabin!
Interior

The Reubling House - Modern-rustic Cabin!

3.0 star property
10.0 out of 10, Exceptional, (1)
The Reubling House - Modern-rustic Cabin!
Pet-friendly Pacific Cottage Near Purina Farms!
Community center with a front door, porch, and grassy area for outdoor gatherings.

Pet-friendly Pacific Cottage Near Purina Farms!

3.0 star property
Pet-friendly Pacific Cottage Near Purina Farms!
St Louis Vacation Rental 4 Mi to Airport!
Situated on a well-maintained lawn, this two-story house features a gabled roof and a front porch with a staircase.

St Louis Vacation Rental 4 Mi to Airport!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The house was spacious and nice "
St Louis Vacation Rental 4 Mi to Airport!
St Louis Home < 1 Mi to Forest Park!
Enjoy a serene atmosphere in this backyard with a well-maintained lawn, patio, and lush greenery.

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!
Quiet Lakefront Cottage With Dock & Resort Access!
Relax on the deck with a view of the river and surrounding greenery, surrounded by comfortable seating and lush potted plants.

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!
Spacious O'fallon Vacation Home: 30 Mi to St Louis
Stunning two-story home with a central entrance, porch, and beautifully manicured lawn.

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

3.0 star property
Spacious O'fallon Vacation Home: 30 Mi to St Louis
Home 2 Mi to Dtwn St Louis: Great for Families!
Three townhouses with unique architectural styles stand on a quiet street, each with a front door, windows, and steps leading to the entrance.

Home 2 Mi to Dtwn St Louis: Great for Families!

3.0 star property
Home 2 Mi to Dtwn St Louis: Great for Families!
Historic Marthasville Getaway w/ Shared Amenities!
Interior

Historic Marthasville Getaway w/ Shared Amenities!

3.0 star property
Historic Marthasville Getaway w/ Shared Amenities!
Cozy Augusta Home w/ Porch: Walk to Katy Trail!
Enjoy a quiet moment on the covered porch with a bench and table overlooking the street and neighboring homes.

Cozy Augusta Home w/ Porch: Walk to Katy Trail!

3.0 star property
Cozy Augusta Home w/ Porch: Walk to Katy Trail!
Missouri Retreat w/ Deck, Grill & Shuffleboard!
Interior

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!
Historic Marthasville Home w/ Shared Amenities!
Interior

Historic Marthasville Home w/ Shared Amenities!

3.0 star property
Historic Marthasville Home w/ Shared Amenities!
Serene Pacific Getaway: Deck, Grill & Fire Pit!
Interior

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!
Interior

'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!
9 Mi to Forest Park: Pet-friendly Home in St Louis
Stunning home with a brick facade, large windows, and a flat roof, featuring a garage door and inviting front porch.

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
Peaceful Country Home in Serene Setting With Yard
Interior

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!
Enjoy a serene outdoor space with a grassy lawn, trees, and a small garden.

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
Relax on the porch with two comfortable chairs and a small table, surrounded by a charming suburban neighborhood.

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
Vino Villa Wine Country Gem: Patio & Grill
Relax on the porch with a view of the surrounding countryside, featuring a comfortable rocking chair and a small table.

Vino Villa Wine Country Gem: Patio & Grill

3.0 star property
Vino Villa Wine Country Gem: Patio & Grill
Home w/ Trail Access on 19 Acres in Wright City!
Interior

Home w/ Trail Access on 19 Acres in Wright City!

3.0 star property
Home w/ Trail Access on 19 Acres in Wright City!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

St. Louis Union Station Hotel, Curio Collection by Hilton

St. Louis Union Station Hotel, Curio Collection by Hilton

10/10 Excellent
"Amazing"
Autumn 2-night trip
Posted 19 hours ago
St. Louis Union Station Hotel, Curio Collection by Hilton

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 42 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!