Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Bevo Mill
4.9 out of 5 average rating, 462 reviews

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Guest favourite
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, 696 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!

Top guest favourite
A formal dining area is presented with a wooden table set for four, surrounded by comfortable chairs. A woven area rug covers the warm wooden floor. Bright natural light streams through large windows, illuminating the space, which is accented by a bold orange feature wall.
Home in Princeton Heights
4.99 out of 5 average rating, 186 reviews

South Hampton Hideaway-King Bed-2BR-Close to parks

Home was unavailable for the past 12 months. Enjoy your stay in this comfortable, and historic second floor duplex in one of St. Louis City’s safest neighborhoods! This home is centrally located, a short walk or drive from parks, restaurants, and local attractions. Minutes away from everything! This spacious 1400 sq/ft home is full of warm and welcoming boho chic décor. King memory foam bed and queen Casper hybrid mattress. Fully equipped kitchen and coffee bar. Wifi and parking are included!

Top guest favourite
The living room features a cozy arrangement with a dark gray sectional couch adorned with cushions and a throw blanket. A wooden console table holds a table lamp, while natural light filters in through large windows, illuminating the textured area rug and simple decor.
Flat in North Hampton
5 out of 5 average rating, 248 reviews

Centrally Located Mid-Century Modern Retreat

Make yourself at home in the thoughtfully restored historic apartment located in the heart of St. Louis City which boasts both historic and modern elements. You will be minutes away from all major highways, eateries, attractions, and entertainment the city has to offer. "Come stay at this mid-century modern retreat, you'll be central to everything St. Louis has to offer and I'm committed to making your stay the best and safest possible using an enhanced cleaning process! " - Sean, Your Host

Top guest favourite
A modern kitchen area features white cabinetry and a kitchen island with three cushioned stools. Pendant lights hang above the island, illuminating the space. A doorway leads to another room, with a glimpse of additional kitchen appliances visible in the background.
Flat in St. Charles Historic District
4.94 out of 5 average rating, 398 reviews

Charming Pop Lucks Guest Suite in 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.

Guest favourite
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, 314 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

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, 120 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!

Top guest favourite
A living room features exposed brick walls, a comfortable gray couch, and a black wicker chair. A flat-screen television is mounted on one wall, while natural light fills the space through two windows. A vibrant area rug adds color to the hardwood floor.
Home in Saint Charles
4.96 out of 5 average rating, 300 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 late 1800'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.

Top guest favourite
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, 192 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!

Guest favourite
A comfortable living room features a blue sofa, accompanied by a green chair and a wooden dining table. Natural light enters through a window with patterned drapes, illuminating the neutral walls and a decorative area rug. A wall clock and framed art complete the space.
Flat in Lindenwood Park
4.87 out of 5 average rating, 222 reviews

Warriors Rest and Repose in St. Louis Hills

This first floor apartment is part of a 4-unit building on Jamieson. It is in St. Louis Hills neighborhood, a community with grocery and retail stores on the main drags – Chippewa and Hampton, with easy reach to city parks and the River Des Peres Greenway Trail. It is well-placed for all city visitors, here for excursions or family get-togethers, medical visits or business travelers, where visitors can rest and repose for another day of fun!

Top guest favourite
A bright living space is presented with a comfortable gray sofa and a round wooden coffee table. A washer and dryer are situated under the staircase, and two potted plants enhance the decor. Natural light enters through multiple windows, illuminating the area.
Cottage in Maplewood
4.98 out of 5 average rating, 504 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.

Guest favourite
A cozy sleeping area is presented with a spacious bed covered in dark bedding. A full-length mirror leans against the wall, reflecting the soft overhead light. Thick curtains adorn the window, and a decorative rug covers the floor.
Flat in St. Louis
4.89 out of 5 average rating, 117 reviews

The Amelia

Cozy studio apartment in Saint Louis close to the Saint Louis International Airport. You’ll be approximately 20 minutes from almost anywhere in Saint Louis: Downtown, Delmar Loop, Zoo, Science Center, Aquarium, shopping centers, and SO much more! With a gated entrance to the property, private keypad entrance, and security cameras this is a perfect place for those looking for a secure place to stay while visiting Saint Louis!

Popular amenities for Chesterfield holiday rentals

Frequently Asked Questions

  • 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.

  • 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.

  • 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.

  • 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.

  • Do apartment rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 apartment 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 Apartment Rentals in Chesterfield?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • 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.

  • 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.

Quick stats about holiday rentals in Chesterfield

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterfield holiday rentals include wifi 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