House holiday rentals in Chesterfield

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Top-rated house rentals in Chesterfield

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Guest favourite
Home in Bevo Mill
4.91 out of 5 average rating, 453 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
A spacious living area features a comfortable brown couch centered around a coffee table. A rustic fireplace is set against a brick wall, providing warmth. Light-colored walls and plenty of windows enhance the natural light flowing into the room.
Home in St. Peters
4.88 out of 5 average rating, 392 reviews

Private Walkout w King Bed & Bath + large livingrm

Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

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, 681 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 comfortable living area features a gray sofa, patterned chairs, and a round coffee table on a natural fiber rug. Light streams through sheer curtains, highlighting the artwork of bicycles on the wall, creating a relaxed setting for guests.
Home in Kirkwood
4.97 out of 5 average rating, 237 reviews

A Kirkwood Cottage, Quaint Suburb of St Louis

Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children. Home has steps to entry & is 4th house from railroad tracks that are up on the hill at end of street.Close easy access to all major highways

Guest favourite
The exterior view of a charming brick house highlights a traditional design with two dormer windows and a bright blue front door. An American flag hangs proudly from the porch, surrounded by well-maintained landscaping that enhances the welcoming appearance.
Home in Saint Charles
4.9 out of 5 average rating, 272 reviews

Tompkins Street Retreat

Relax in this two-bedroom, two-bath house with a backyard patio and firepit with a privacy fence. Walk to unique shopping and entertainment on Historic St. Charles Main Street. Local wineries and St. Louis attractions are a short drive away. Enjoy a comfortable living room with a large TV and a fully equipped kitchen for special meals. Unwind after an active day with a meal, drinks under the pergola, and a great night's sleep in our king-size bed. We also offer FREE off-street/garage parking.

Top Guest favourite
A charming brick exterior is shown, featuring a covered front porch with steps leading to the entrance. Lush greenery surrounds the house, complemented by a well-maintained lawn and a tree partially obscuring the view. The sky appears bright and clear with scattered clouds.
Home in Dogtown
4.92 out of 5 average rating, 146 reviews

Dog Friendly! Dogtown Getaway Mins from Zoo

Relax with the whole family in this peaceful 1 bedroom home in the highly desirable Dogtown neighborhood in St.Louis. The home is located just minutes away from the amazing St.Louis Zoo, historic Forest Park and some of the best restaurants in town. Getting around to the other sights in town will be easy with hwy 40 and 44 just minutes away as well! With a giant king bed, high speed internet, free parking, and a big private fenced in backyard this house can easily be your home away from home!

Guest favourite
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Caseyville
4.9 out of 5 average rating, 105 reviews

Relaxing Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Top Guest favourite
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
4.95 out of 5 average rating, 374 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 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, 294 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.

Guest favourite
Home in St. Louis
4.95 out of 5 average rating, 162 reviews

Family Friendly Cozy Home w/ Lrg Fenced Yard

**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station

Top Guest favourite
A cozy studio layout features a spacious queen bed adorned with floral bedding. A round dining table with four chairs is positioned nearby, surrounded by warm hardwood flooring. Natural light enters through a window, enhancing the inviting atmosphere.
Home in Villa Ridge
4.94 out of 5 average rating, 178 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 favourite
The living room features a plush, teal sofa paired with two brown armchairs. A coffee table sits centrally on an ornate purple and pink rug. A flat-screen TV displays the Netflix logo, while a decorative fireplace adds a warm touch to the space.
Home in St. Louis
4.98 out of 5 average rating, 203 reviews

Entire home-King bed-2 Bedroom-Close to Everything

Kick back and relax in this calm, stylish space. Located in one of the safest neighborhoods in St. Louis, this home is just a short walk or drive from parks, restaurants, and local attractions. Take in all of St. Louis as you'll be only minutes away from everything! This beautiful, single family home is full of warm and welcoming boho chic decor. Both king and queen beds are memory foam hybrids. Fully equipped kitchen and coffee bar. Wifi, laundry, and parking are included.

Popular amenities for Chesterfield house rentals

Quick stats about house rentals in Chesterfield

  • Total holiday rentals

    Explore 10 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 70 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Chesterfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!