Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favorite

Tiny home in Pacific

4.96 out of 5 average rating, 161 reviews

Route 66 railroad shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

Aug 21 – 28

G$24,269 GYD per night

Guest favorite

Home in Saint Charles

4.98 out of 5 average rating, 489 reviews

301 Guesthouse SuperHost/Shop Discounts/Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Jan 5 – 12

G$23,787 GYD per night

Guest favorite

Guest suite in Saint Charles

4.95 out of 5 average rating, 296 reviews

Creekside Suite - Peaceful, Spacious, and Comfy

Enjoy your stay in a spacious walkout basement-level suite that includes bedroom, bathroom, living/dining room & patio. Bedroom has queen bed, dresser, desk & TV. Living room has futon, books, games & TV. TVs have Netflix. Suite has minifridge, microwave, toaster & coffee-maker. Eat at the dining table or sit up to the window counter to look out on the creek & woodlands behind the house. Situated in a quiet, safe neighborhood with parks & ponds. Just 8 miles from historic downtown St Charles.

Jun 27 – Jul 4

G$21,973 GYD per night

Guest favorite

Apartment in Saint Charles

4.95 out of 5 average rating, 278 reviews

Pop Lucks Guest Suite in Historic Old St. Charles

Welcome to Pop Luck's Guest Suite! This adorable gem represents everything you love about Old St. Charles. This cozy suite is just steps away from the heart of Main Street, restaurants, and all the action St. Charles has to offer. Pop Luck's is a charming one-bedroom, with an open and airy living room and kitchen. It has natural light and high ceilings throughout. It's farmhouse cottage decor makes for a relaxing place to rest. Also, check out our sister suite The Ella Rose, right next door.

Jun 5 – 12

G$25,037 GYD per night

Guest favorite

Bungalow in Saint Charles

4.99 out of 5 average rating, 161 reviews

Patio House, secluded in heartbeat of Main Street

The Patio is nestled in the heart of historic St. Charles a few steps from Main Street, Katy Trail, Missouri River, Antique and Boutique Shopping, Restaurants Bars and More, Several Wedding venues are within walking distance of the property as well. In addition to your well appointed unit, this property has as much outside as it does in. Take your coffee, wine, water and enjoy our patio, complete with fire table, dining table edged with lush plantings for privacy. PLEASE NOTE NO SMOKING

Jan 21 – 28

G$23,334 GYD per night

Guest favorite

Cottage in Saint Charles

4.97 out of 5 average rating, 265 reviews

The Rose Cottage -a short walk to Historic Main St

The Cottage has a 2 guest maximum Updated 1 bedroom home a three minute walk from historic Main Street and festivals like Oktoberfest, Christmas Traditions and Festival of the Little Hills, the Lewis and Clark Boat House, Foundry Arts Center, Katy Trail and more! Located 10 minutes from the airport , 2 minutes from Ameristar Casino and Bass Pro Shop. 25 minutes from downtown St. Louis, The Arch, Forest Park, Zoo, Art Museum, History Museum and Busch Stadium-home of Cardinals Baseball!

Aug 22 – 29

G$31,463 GYD per night

Guest favorite

Farm stay in Lake Saint Louis

4.92 out of 5 average rating, 191 reviews

Updated Farmhouse 2 bd 2 acres

Updated Farm House on 2 acres,3 beds, 1 bth, this house has 2 bedroom with 3 beds, a fully equipped kitchen, living room, a full bathroom,double sinks,and laundry facilities, this house is a duplex, with 2 separate units, the upstairs is for Airbnb guest, the lower unit has a tenant, each unit has its own space and entrance. 25 minutes from the St. Louis Airport, close to the Missouri Wineries, Bush wild life area, and only 10 minutes to the Katie Trail along the Missouri River.

Jan 27 – Feb 3

G$25,103 GYD per night

Guest favorite

Home in Ballwin

4.94 out of 5 average rating, 136 reviews

Entire lower level of our home w/Paris Theme

Our home is located in a quiet West St. Louis County neighborhood. The lower/walkout of this place is your home away from home. It has a private entrance from a walk around sidewalk to the backyard. You will have the entire lower level of our home. We live in the upstairs or first floor of this home. Our place is best suited for one couple, solo adventurers, business travelers, and one family (with kids). This space has been recently remodeled with a French Parisian theme!

Jul 20 – 27

G$21,033 GYD per night

Guest favorite

Home in Saint Charles

4.97 out of 5 average rating, 175 reviews

Bright & Cozy Shotgun DPX 1 Block from Historic DT

Admire this unique historic home's design with brand new amenities and antique details that give a fresh and charming feel. Built in the 1930's, this half of the duplex has a typical shotgun layout with ten-foot ceilings giving a spacious feel. The front door leads directly to the living room, then into the bedroom, both of which have the original hard wood floors. The back of the house has the kitchen, with exposed brick, a dining area, and a bathroom with a washer and dryer.

Dec 20 – 27

G$27,621 GYD per night

Guest favorite

Home in St. Louis

4.98 out of 5 average rating, 511 reviews

Garden Cottage-Safe Private Parking!

Thoughtfully renovated cozy bungalow offering a lush vibrant landscaped garden, meandering brick patio & deck overlooking waterfall pond w/ Koi fish. We lovingly restored our efficient space with a mix of old & new furnishings and updated appliances. A Romantic luxurious vibe ❤️ The perfect nest for two! Our quiet safe neighborhood is home to fabulous restaurants, bars, coffee shops and galleries. Close to everything including Hwys 40, 44, 55 . PLUS safe private parking!

Sep 26 – Oct 3

G$26,583 GYD per night

Guest favorite

Farm stay in Grafton

4.97 out of 5 average rating, 203 reviews

Pere Ridge Tree Escape

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck and hot tub that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a short drive to Grafton. It is a light filled studio cabin with modern touches .

Sep 19 – 26

G$32,709 GYD per night

Guest favorite

Home in Dittmer

4.95 out of 5 average rating, 356 reviews

Honeymoon Suite Camp Skullbone In The Woods

Romantic quiet cozy chalet for two! Vintage décor with all the modern amenities of home. Relax inside to unwind, kick back and watch a movie, surf the web via free wi-fi, curl up with a good book, open up a board game for a friendly challenge or share a drink with that special someone. Want some fresh country air? Lace-up those hiking boots and take like Camp Skullbones. . Enjoy the stars on the intimate deck with the glow from the gas fire pit.

Sep 21 – 28

G$31,784 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesterfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chesterfield's top sights

St. Louis Premium Outlets33 locals recommend

Topgolf27 locals recommend

Chesterfield Mall10 locals recommend

The Butterfly House54 locals recommend

The Cheesecake Factory3 locals recommend

St. Luke's Hospital4 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Tiny home in Saint Ann

4.92 out of 5 average rating, 137 reviews

Forest Edge Tiny House | 8 Min to Airport

May 15 – 22

G$34,120 GYD per night

Guest favorite

Home in St. Louis

4.84 out of 5 average rating, 101 reviews

Cheerful 1-bedroom, red brick, historic home

Mar 9 – 16

G$13,438 GYD per night

Guest favorite

Home in Maryland Heights

4.82 out of 5 average rating, 162 reviews

The Red Door ★ Comfy 3 Bdr Home - Quiet Cul-de-sac

Aug 14 – 21

G$31,304 GYD per night

Guest favorite

Guesthouse in St. Louis

4.95 out of 5 average rating, 769 reviews

The Garage Mahal

Feb 7 – 14

G$15,757 GYD per night

Guest favorite

Guest suite in Wildwood

4.84 out of 5 average rating, 140 reviews

Spacious suite,private patio,safe,horse property

Feb 10 – 17

G$28,571 GYD per night

Superhost

Tiny home in Pacific

4.89 out of 5 average rating, 483 reviews

Route 66 Cozy Cottage

Dec 6 – 13

G$22,718 GYD per night

Guest favorite

Home in Saint Charles

5.0 out of 5 average rating, 221 reviews

Rustic Handcrafted Japanese-Style Home by OldTown

Jan 22 – 29

G$41,774 GYD per night

Guest favorite

Home in Saint Charles

4.91 out of 5 average rating, 151 reviews

Tompkins Street Retreat

Oct 9 – 16

G$29,968 GYD per night

Show all

Quick stats about vacation rentals in Chesterfield

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
180 reviews

Frequently Asked Questions

Do house rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Chesterfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Chesterfield?
Experience the best of Chesterfield with our hotel rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Chesterfield have wifi?
Absolutely! We offer over 10 hotel rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Hotel Rentals in Chesterfield?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do hotel rentals in Chesterfield have free parking?
Absolutely! We offer over 10 hotel rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 10 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Chesterfield?
Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Meadowbrook Country Club Estates, and over 50 vacation rentals in Brook Hill Estates.

Vacation rentals in Chesterfield

Top-rated vacation rentals in Chesterfield

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

Other great vacation rentals in Chesterfield

Tiny home in Saint Ann

Home in St. Louis

Home in Maryland Heights

Guesthouse in St. Louis

Guest suite in Wildwood

Tiny home in Pacific

Home in Saint Charles

Home in Saint Charles

Quick stats about vacation rentals in Chesterfield

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Chesterfield have a kitchen?

Are there pet-friendly vacation rentals in Chesterfield?

Do house rentals in Chesterfield have air conditioning?

How much does it cost to stay in hotel rentals in Chesterfield?

Do hotel rentals in Chesterfield have wifi?

Are there family-friendly vacation rentals in Chesterfield?

What are the most popular amenities for Hotel Rentals in Chesterfield?

Do hotel rentals in Chesterfield have free parking?

Are there vacation rentals with a dedicated workspace in Chesterfield?

Where should I stay in Chesterfield?

Destinations to explore