
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

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!

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

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.

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!

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.

*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.

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.

Honeymoon Suite at Camp Skullbone In The Woods
Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

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

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.

Adorable Garden Cottage - Safe Lit Private Parking
Mindfully 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
Popular amenities for Chesterfield house rentals
House rentals with a pool

Willow Creek: Mid-Century Oasis

Private indoor pool & sauna

Clark Brick House w/ Pool | Historic St. Charles

Blair's Pool House - Creve Couer Hot Tub Game Room

Spacious, Family Friendly, Great Location w/ Pool

Innsbrook Woods | Pool, Hot Tub & Tennis Court

Roomy Oasis with hot tub on the Hill!

Sunset Mountain Forest Privacy
Weekly house rentals

Separate Entry Basement Apartment 1BR, 1BA

Family friendly 3bd home! Longer stays available

Private Oasis w/hot tub

The Ladybug Inn

Top Rated | Perfect Location 3BR + Epic Game Room

Botanical Gardens Bliss

3+ private acres, Koi fish pond, garage parking

Grammy's Place~A Loving Home
Private house rentals

Perfect Getaway 3BR/3BA Home

Skip Hotels! Luxe Stay, Hot Tub, Spacious Game RM

Luxurious, spa-like retreat steps from Main St.

Victorian Gem Steps from Main St - Sleeps 9 & Pets

Elsah’s Finn Inn-new restaurant across the street!

Serene & Cozy Cabin + LAKE! Near Purina & SixFlags

Modern Country Oasis

Family/hot tub/foosball/fire pit/big yard
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!
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- Central West End
- Busch Stadium
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- City Museum
- Missouri Botanical Garden
- St. Louis Aquarium at Union Station
- Cuivre River State Park
- Pere Marquette State Park
- Castlewood State Park
- Hidden Valley Ski Resort
- Meramec State Park
- Grafton Winery the Vineyards
- The Winery at Aerie's Resort
- Cathedral Basilica of Saint Louis
- Bellerive Country Club
- Raging Rivers WaterPark
- Norwood Hills Country Club
- Saint Louis Science Center
- Adventure Valley Zipline Tours and Paintball Park
- Noboleis Vineyards
- Missouri History Museum
- Old Warson Country Club




