Chesterfield Vacation Rentals from AED 405: Search Short-Term Rentals

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Our top choices for Chesterfield vacation rentals

A spacious living area with a high ceiling, wooden beams, a fireplace, a dining area, and a cozy seating arrangement.

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Wildwood

Jennifer M.

AED 1,308 total

includes taxes & fees

16 Nov - 17 Nov

A set of stone steps leading to a garage with a car parked inside.

2. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Ballwin

Keith K.

AED 511 total

includes taxes & fees

21 Nov - 22 Nov

A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

3. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Westport

Anonymous traveler

AED 235 total

includes taxes & fees

30 Nov - 1 Dec

A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

4. Casa de Saint Charles

Saint Charles

Xavier H.

AED 1,082 total

includes taxes & fees

12 Nov - 13 Nov

A residential building with a patio area featuring outdoor furniture and string lights.

5. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

St. Peters

Lynn D.

AED 1,025 total

includes taxes & fees

18 Nov - 19 Nov

A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

6. Prime Loft of Main Street

St. Charles Historic District

Richard W.

AED 974 total

includes taxes & fees

15 Nov - 16 Nov

A spacious living area with a wooden floor, a dining table with chairs, a flat-screen TV mounted on the wall, and a kitchen area with modern appliances.

7. The Lofts of North Main Street

St. Charles Historic District

Liberty A.

AED 857 total

includes taxes & fees

12 Nov - 13 Nov

A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

8. Home Near Main with Pet-Friendly Yard and Office

St. Charles Historic District

Jessica S.

AED 957 total

includes taxes & fees

15 Nov - 16 Nov

A staircase with white railings and a ceiling fan.

9. Amazing Renovated Historic Loft on Main Street

St. Charles Historic District

Rebecca F.

AED 974 total

includes taxes & fees

15 Nov - 16 Nov

A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

10. Dog-Friendly Studio on Historic Main Street

St. Charles Historic District

Sarah C.

AED 789 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a green sofa, a wooden coffee table, and hanging plants.

11. Safe and private apt-Near Forest Park-Free parking

Dogtown

Cornelius

An outdoor hot tub area with seating and a covered patio.

12. Hot Tub + 2 King Beds | Private Walk-Out Suite

Saint Charles

Beth S.

A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

13. Historic Main St. Customs House Upstairs Apartment

St. Charles Historic District

Margaret A.

AED 1,270 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with a built-in refrigerator, a dining area with a wooden table and benches, a gray sofa, and large windows providing natural light.

14. Chic Minimalist Gem w/ Fenced Backyard + W/D

Princeton Heights

Dave

A hotel lobby with a staircase, a reception desk, and a seating area.

15. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

Westport

Anonymous traveler

AED 238 total

includes taxes & fees

29 Nov - 30 Nov

A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

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

St. Charles Historic District

Melissa S.

AED 872 total

includes taxes & fees

15 Nov - 16 Nov

A spacious foyer with a grand staircase, a piano, and a large rug.

17. White House at Grand Central

Grand Center

Priscilla

AED 455 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

18. 6653 2S | Jewel of Central St. Louis

Dogtown

Ashley C.

AED 496 total

includes taxes & fees

16 Nov - 17 Nov

A living room with a flat-screen TV, a sofa with patterned cushions, a coffee table, and a rug.

19. Cottage on Historic Main Street- Low Cleaning fee

St. Charles Historic District

Elizabeth D.

AED 1,100 total

includes taxes & fees

17 Nov - 18 Nov

A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

20. Spacious, 3 bedroom home, finished basement on quiet court

St. Peters

ed n.

AED 1,500 total

includes taxes & fees

17 Nov - 18 Nov

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Top Chesterfield Hotel Reviews

Pear Tree Inn St. Louis Airport

10/10 Excellent

"They have free popcorn, salsa and chips, free soda pop and drinks in the evening hour."

Clayton Plaza Hotel & Extended Stay

8/10 Good

"The room was very clean; the cleaning staff was somewhat hesitant to provide me with extra towels and wash cloths upon request. The breakfast bar was very nice; however, on the weekend the omlet bar was not opened until 7:00am (omlets were cooked to specification). You could not carry food out to your room or fix a plate to take with you on the road. This was very inconveient for me as I needed to leave hotel by 6:30am to drive to St. Louis Convention Center 20 miles away, park in 9th St garage and walk to 11th St to the Convention Center for morning services at 7am. It would have been nice to have been able to take a cup of fruit with me. The hotel had lots of garage parking; however, there were no lights in the garage except a flood light by the door entrance that led into the hotel. Parking at night was uncanningly frightening because once you parked your car, if you were not close to the flood light that lit up the door entrance or didn't have a flash light, it was pitch black. Thankfully, I had a very powewrful flashlight I keep in my car which came in handy. The hotel does not provide any other dining other than breakfast."

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals in Chesterfield near Sophia M. Sachs Butterfly House, 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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: Visitors like this Chesterfield vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chesterfield?

Choose from 8 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 Myseum, 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.

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Check prices for these dates

Our top choices for Chesterfield vacation rentals

1. Private 3-Acre Retreat • Koi Pond & Waterfall

2. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

3. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

4. Casa de Saint Charles

5. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

6. Prime Loft of Main Street

7. The Lofts of North Main Street

8. Home Near Main with Pet-Friendly Yard and Office

9. Amazing Renovated Historic Loft on Main Street

10. Dog-Friendly Studio on Historic Main Street

11. Safe and private apt-Near Forest Park-Free parking

12. Hot Tub + 2 King Beds | Private Walk-Out Suite

13. Historic Main St. Customs House Upstairs Apartment

14. Chic Minimalist Gem w/ Fenced Backyard + W/D

15. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

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

17. White House at Grand Central

18. 6653 2S | Jewel of Central St. Louis

19. Cottage on Historic Main Street- Low Cleaning fee

20. Spacious, 3 bedroom home, finished basement on quiet court

Find vacation rentals that suit your style

Top Chesterfield Hotel Reviews

Pear Tree Inn St. Louis Airport

Drury Plaza Hotel St. Louis Union Station

Clayton Plaza Hotel & Extended Stay

Pear Tree Inn St. Louis Near Union Station

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Courtyard by Marriott St. Louis Downtown/Convention Center

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

Frequently asked questions

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