Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Top guest favorite
The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.
Home in Saint Charles
4.97 out of 5 average rating, 704 reviews

301 Guesthouse- Historic Main street-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!

Guest favorite
A charming exterior is shown, featuring a light blue façade with white trim. Windows are framed with dark shutters. A small white picket fence surrounds the front yard filled with greenery and plants, while a wreath decorates the door, enhancing the home's welcoming appearance.
Home in St. Charles Historic District
4.94 out of 5 average rating, 180 reviews

Charming 2/1 in St Charles Historic Main Street

Come relax and play! Half a block from historic Main Street in City of St Charles. This stay is everything you could want. Cozy, charming, private with outdoor area for seating and dinning table. Off-street parking, laundry. Go shopping in the historic downtown shops, go to concerts, casinos or just stay in and enjoy! Walk to restaurants and the Katy Trail! Come be our guest! Or stay in put and cook the kitchen has everything you need! We are a strictly non smoking stay, inside or outside.

Guest favorite
A small dining area features a square table surrounded by four black stools. A potted flower adds a touch of color to the table. Modern flooring in shades of gray highlights the space, leading toward a kitchen area in the background.
Guesthouse in St. Louis
4.91 out of 5 average rating, 107 reviews

The Blue Door in Creve Coeur

Perfect location for quick access to everything StL. Come home to a peaceful and spacious smokefree property. Sit on the patio and watch deer and squirrels running around. The main area is large and open concept. Bedrooms are big and comfortable, with their own fireplace heater. There is plenty of closet room. Laundry room included with a folding table and an iron. Spacious bathroom with a large shower with a seat! The Walkway to the frontdoor is down a small incline. please see pictures.

Guest favorite
A treehouse-style rental is nestled among vibrant autumn foliage, with wooden steps leading up to the entrance. The structure features a private front porch, framed by surrounding trees and a gravel path, conveying a natural and serene atmosphere.
Guest suite in Dardenne Prairie
4.88 out of 5 average rating, 316 reviews

Treehouse Spa Suite

Treehouse Day Spa is nestled on 3 wooded acres in St.Charles County. There is a subdivision next to me but I have my trees!!! Get away from it all while being close to it all at the same time. Augusta wineries, Main Street St. Charles and the Streets of Cottleville are all within minutes of the location! There are two rental units in the treehouse: The spa suite and the penthouse. They each have a separate entrance and are private spaces. Recharge your battery! Regroup Relax Refresh

Guest favorite
The living room showcases a blend of seating options, including a black futon and a brown leather sofa, complemented by a colorful area rug. Natural light filters through patterned curtains, illuminating the space which features a television and decorative touches.
Home in Saint Charles
4.95 out of 5 average rating, 132 reviews

Cozy Mid-Century Modern Townhome

This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

Superhost
A grey sectional sofa is positioned next to a circular glass table, creating a comfortable seating area. Natural light floods the space through large glass doors leading to the outside. A potted plant adds greenery, while wall decor spells out 'HOME.'
Home in St. Louis
4.91 out of 5 average rating, 124 reviews

St. Louis Home away from Home!

Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

Guest favorite
The exterior of a charming century home showcases a covered front porch with white railings and a welcoming entrance. Lush greenery and flower beds line the stone steps leading to the porch, enhancing the inviting character of the property.
Home in Saint Charles
4.94 out of 5 average rating, 394 reviews

*HotTub* The Jewel on 5th-2br2b-near Historic Main

A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. Can sleep 6.

Top guest favorite
Home in Villa Ridge
4.94 out of 5 average rating, 181 reviews

Serenity Valley (No Cleaning Fee- No pets please)

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

Top guest favorite
The exterior of the house features a well-maintained lawn with shrubbery and a covered porch. A cozy seating area with a modern coffee table is shown, complemented by a sectional sofa. A well-equipped kitchen with appliances and a dining table set for six are also visible. A serene bedroom showcases a spacious bed with soft linens.
Home in Saint Charles
4.99 out of 5 average rating, 194 reviews

Little House By Main St -5 4K TV's- 1-75 Inch -1GB

Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

Superhost
A bright kitchen featuring light green cabinetry and white countertops. An island with a circular design provides additional workspace. Natural light filters through the shutters above the sink, illuminating the dining area with a wooden table surrounded by four chairs.
Home in Creve Coeur
4.88 out of 5 average rating, 222 reviews

Home away from Home St. Louis Cnty Ladue Schools

15 min to Norwood Hills CC. Centrally located in Safe St. Louis County, Olivette/Creve Coeur area near many attractions, businesses, Universities, etc. Harkte Nursery is 2 houses away with farm fresh produce!! Lambert Intl Airport 13 min 7.7 miles Busch Stadium and St. Louis Ballpark Village, The Arch 20 min 13.8 miles Washington University 13 min 6.4 miles St Louis University 10 min St Louis Zoo, Forest Park, Science Center, Art Museum

Guest favorite
A single-story home is depicted with a metal roof and a front door featuring a decorative window. Brightly colored flower pots filled with blooms are arranged along the path, complemented by landscaped greenery surrounding the property.
Tiny home in Gray Summit
4.9 out of 5 average rating, 711 reviews

Route 66 Cozy Cottage

* Fast Wifi (Spectrum) * Keypad entry (no keys to keep track of) * Private driveway by the front door for easy access to carry luggage in and out * Huge yard for dogs, kids or even adults to play * Lovely outdoor patio with plenty of comfortable seating and beautiful landscaping * For the kiddos- toys, books, and games (puzzles and games for adults too) * Essentials for your furbabies as well - treats, leashes, food & water bowls, waste bags, towels

Top guest favorite
The spacious wooden gazebo features a hexagonal design with ample outdoor seating, including comfortable couches and chairs. A propane fire pit is centered on a wooden deck, complemented by overhead fans for ventilation and comfort during warm evenings.
Home in Wentzville
4.98 out of 5 average rating, 115 reviews

Spacious 6BR Hill Manor w Private Spa

Perfect for group stays, families, and wedding guests, this modern smart home offers a comfortable and convenient stay in a prime location near Highway 64. Enjoy a fully equipped "chef’s kitchen", eight 4K smart TVs, high speed WiFi, and a private office perfect for remote work. Smart Nest technology enhances comfort, all just 30 minutes from STL Airport with easy access to dining, shopping, and top attractions.

Popular amenities for Chesterfield vacation rentals

Frequently Asked Questions

  • 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.

  • How much does it cost to stay in apartment rentals in Chesterfield?

    Experience the best of Chesterfield with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chesterfield?

    Four-legged friends are welcome in Chesterfield. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Chesterfield?

    Yes! Work meets play with ease at over 20 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Chesterfield vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chesterfield, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Brook Hill Estates, and over 40 vacation rentals in Meadowbrook Country Club Estates.

  • Do apartment rentals in Chesterfield have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Chesterfield have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • Do house rentals in Chesterfield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 40 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,297 GYD per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.6 Average rating

    Chesterfield stays receive an average rating of 4.6 out of 5 from guests