Photo by Michelle E

Search Chesterfield Cottage Rentals from CA $288

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Chesterfield Cottages

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, (200)
"We are delighted to have found this beautiful VRBO and the quaint area of St. Charles! We were coming to St Louis to see our Phillies play the Cardinals but didn’t want to stay in the city. This was a PERFECT spot. Close enough to go exploring the city, but then coming back to the quiet historic streets of St Charles. The Guest House was cozy and unique with a peaceful view of the Missouri River just a golf stroke away. Steeped in history but certainly not lacking any modern amenities needed....
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Dock & Resort Perks: Quiet Lakefront Cottage
Terrace/patio

Dock & Resort Perks: Quiet Lakefront Cottage

9.6 out of 10, Exceptional, (125)
"All the comforts of home. Resort was safe and the only noises we heard were birds chirping. Communication with the hosts was spot on."
Dock & Resort Perks: Quiet Lakefront Cottage
Historic headquarters of city founder! Gated parking!
Smart TV, books

Historic headquarters of city founder! Gated parking!

10.0 out of 10, Exceptional, (42)
"Property is as described, and better. We had a wonderful, short stay and found the Headquarters to be a perfect jumping off point for exploring and enjoying Saint Charles. Host was very accommodating and quick to respond to questions. Clean, comfortable, well stocked kitchen, and unbeatable location. Charming property- there was even a whitetail bunny hopping around the front yard when I stepped out with my coffee in the morning! Will absolutely look to book this property for future visits....
Historic headquarters of city founder! Gated parking!
Beautiful Cottage on Large one Acre Private Lot
Terrace/patio

Beautiful Cottage on Large one Acre Private Lot

10.0 out of 10, Exceptional, (16)
"Even tho our trip was cut short with Mother Nature shenanigans. We had a great time here. The host was very responsive and helpful. Will stay here again "
Beautiful Cottage on Large one Acre Private Lot
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!
Tarnhouse Lakefront Cottage by StayLage
TV, fireplace, stereo

Tarnhouse Lakefront Cottage by StayLage

Tarnhouse Lakefront Cottage by StayLage
The Marigold Cottage by StayLage
TV, fireplace

The Marigold Cottage by StayLage

10.0 out of 10, Exceptional, (1)
The Marigold Cottage by StayLage
Delightful Cottage by Clayton
Exterior

Delightful Cottage by Clayton

10.0 out of 10, Exceptional, (1)
"This house was so cute and cozy! It has a great location within 10 miles from almost everything -zoo, magic house, you name it! It was perfect for our weekend getaway."
Delightful Cottage by Clayton
St Louis Vacation Rental 4 Mi to Airport!
House (4 Bedrooms) | 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!
St Louis Home < 1 Mi to Forest Park!
Interior

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

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

3.0 star property
Home 2 Mi to Dtwn St Louis: Great for Families!
Unique Cottage - Dog Friendly - Close to Purina
Fridge, microwave, oven, stovetop

Unique Cottage - Dog Friendly - Close to Purina

9.4 out of 10, Exceptional, (3)
"This was our second place to stay in Pacific! Our previous house was a tiny home there and it was a nightmare! I would definitely stay here again!"
Unique Cottage - Dog Friendly - Close to Purina
Hound Haus - Dog Friendly, near Purina Farms and WashMO
Interior

Hound Haus - Dog Friendly, near Purina Farms and WashMO

9.8 out of 10, Exceptional, (28)
"Very cute and cozy. Everything you need for a short or long stay. We loved drinking our morning coffee out on the bedroom balcony. Such a pretty location as well."
The price is CA $288
CA $384 total
includes taxes & fees
May 5 - May 6
Hound Haus - Dog Friendly, near Purina Farms and WashMO
Pet-friendly Pacific Cottage Near Purina Farms!
House (2 Bedrooms) | Interior

Pet-friendly Pacific Cottage Near Purina Farms!

3.0 star property
Pet-friendly Pacific Cottage Near Purina Farms!
Modern St Louis Vacation Rental Near Benton Park!
House (2 Bedrooms) | Private kitchen

Modern St Louis Vacation Rental Near Benton Park!

3.0 star property
Modern St Louis Vacation Rental Near Benton Park!
The Reubling House - Modern-rustic Cabin!
House (1 Bedroom) | Private kitchen

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 St Louis Home w/ Grill & Backyard
Interior

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
'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!
Historic Marthasville Getaway w/ Shared Amenities!
House (2 Bedrooms) | Private kitchen

Historic Marthasville Getaway w/ Shared Amenities!

3.0 star property
Historic Marthasville Getaway w/ Shared Amenities!
Serene Pacific Getaway: Deck, Grill & Fire Pit!
House (3 Bedrooms) | Interior

Serene Pacific Getaway: Deck, Grill & Fire Pit!

3.0 star property
Serene Pacific Getaway: Deck, Grill & Fire Pit!
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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Other property types in Chesterfield

White House at Grand Central
Comfort Apartment

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (104)
"Did not like the smell of pot with in the building. Location was great to have easy access to many area activities."
The price is CA $127
CA $237 total
includes taxes & fees
May 5 - May 6
White House at Grand Central
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, (200)
"We are delighted to have found this beautiful VRBO and the quaint area of St. Charles! We were coming to St Louis to see our Phillies play the Cardinals but didn’t want to stay in the city. This was a PERFECT spot. Close enough to go exploring the city, but then coming back to the quiet historic streets of St Charles. The Guest House was cozy and unique with a peaceful view of the Missouri River just a golf stroke away. Steeped in history but certainly not lacking any modern amenities needed....
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Funky mini loft in fox park! Pet friendly!!
Private kitchen

Funky mini loft in fox park! Pet friendly!!

7.8 out of 10, Good, (56)
"St. Louis overall wasn’t a vibe, the house inside was pretty cool. I wish the description showed the outside of the house and the location. It was very sketchy but thankfully nothing bad happened lol. My kids enjoyed all the Nicolas Cage stuff inside. Although we won’t be returning it was definitely decent for the price we paid. "
The price is CA $104
CA $216 total
includes taxes & fees
May 11 - May 12
Funky mini loft in fox park! Pet friendly!!
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.