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, 163 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!

Mar 25 – Apr 1

G$22,392 GYD per night

Guest favorite

Home in Saint Charles

4.98 out of 5 average rating, 492 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!

Oct 4 – 11

G$28,350 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 17 – 24

G$21,684 GYD per night

Guest favorite

Bungalow in Saint Charles

4.99 out of 5 average rating, 163 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

Dec 12 – 19

G$23,280 GYD per night

Guest favorite

Cottage in Saint Charles

4.97 out of 5 average rating, 266 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!

May 27 – Jun 3

G$31,390 GYD per night

Guest favorite

Farm stay in Lake Saint Louis

4.92 out of 5 average rating, 194 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.

Nov 18 – 25

G$25,596 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 29 – Aug 5

G$20,984 GYD per night

Guest favorite

Home in Saint Charles

4.97 out of 5 average rating, 178 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 22 – 29

G$27,557 GYD per night

Guest favorite

Home in St. Louis

4.98 out of 5 average rating, 514 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!

Aug 23 – 30

G$27,712 GYD per night

Guest favorite

Farm stay in Grafton

4.97 out of 5 average rating, 204 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 .

Dec 3 – 10

G$31,953 GYD per night

Guest favorite

Home in Dittmer

4.95 out of 5 average rating, 357 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.

Oct 4 – 11

G$32,493 GYD per night

Guest favorite

Cottage in Maplewood

4.98 out of 5 average rating, 367 reviews

Weaver Guest House

This charming, light-filled cottage feels like its own private hideaway, yet it's close to everything St. Louis has to offer. Tucked between trees in a quiet Maplewood neighborhood, it's a 15-minute walk to the MetroLink and a 10-minute drive to Washington University, Webster University, Fontbonne University, Forest Park, and Clayton. Business travelers and families alike will appreciate the washer/dryer, fast WIFI and cable TV.

Oct 7 – 14

G$23,185 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

Whole Foods Market9 locals recommend

The Butterfly House54 locals recommend

The Cheesecake Factory3 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Home in St. Louis

4.84 out of 5 average rating, 102 reviews

Cheerful 1-bedroom, red brick, historic home

Apr 6 – 13

G$13,407 GYD per night

Guest favorite

Apartment in Saint Charles

4.95 out of 5 average rating, 279 reviews

Pop Lucks Guest Suite in Historic Old St. Charles

Jul 2 – 9

G$29,106 GYD per night

Guest favorite

Home in Belleville

4.99 out of 5 average rating, 146 reviews

The Pool House 1-Bedroom Home with Hot Tub & Pool

Jun 18 – 25

G$26,511 GYD per night

Guest favorite

Bungalow in St. Louis

4.99 out of 5 average rating, 293 reviews

Darling Bungalow! King Bed!

Jun 18 – 25

G$22,846 GYD per night

Guest favorite

Home in St. Peters

4.94 out of 5 average rating, 120 reviews

Comfy 3BR home in heart of Saint Peters

Sep 26 – Oct 3

G$29,966 GYD per night

Guest favorite

Tiny home in Saint Ann

4.92 out of 5 average rating, 139 reviews

Forest Edge Tiny House | 8 Min to Airport

May 13 – 20

G$33,905 GYD per night

Guest favorite

Loft in Washington

4.99 out of 5 average rating, 297 reviews

2nd Street Loft - Riverview

Jul 24 – 31

G$20,888 GYD per night

Guest favorite

Guesthouse in St. Louis

4.95 out of 5 average rating, 772 reviews

The Garage Mahal

Dec 16 – 23

G$15,782 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 hotel rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 hotel 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 hotel rentals in Chesterfield have air conditioning?
Absolutely! We offer over 10 hotel 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 house rentals in Chesterfield have wifi?
Absolutely! We offer over 10 house 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 House Rentals in Chesterfield?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, 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

Home in St. Louis

Apartment in Saint Charles

Home in Belleville

Bungalow in St. Louis

Home in St. Peters

Tiny home in Saint Ann

Loft in Washington

Guesthouse in St. Louis

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 hotel rentals in Chesterfield have a kitchen?

Are there pet-friendly vacation rentals in Chesterfield?

Do hotel rentals in Chesterfield have air conditioning?

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

Do house rentals in Chesterfield have wifi?

Are there family-friendly vacation rentals in Chesterfield?

What are the most popular amenities for House 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