
Holiday houses in Chesterfield
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Top-rated holiday rentals in Chesterfield
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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!

Catch The Dream:; An Immersive Equestrian Escape
Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

Romantic Augusta Cottage-Relax & get away!
This cottage is designed to strengthen and refresh couples looking for a getaway from busy life. Relax in the comfortable Living room or prepare a meal in the recently updated fully furnished kitchen. Enjoy your nights in the spacious bedroom furnished with a California King sized bed and TV in the room. Enjoy the private hot tub just steps from the door or use the BBQ pit to create a meal to enjoy together. Area restaurants, wineries & golf are just minutes away! You are sure to enjoy!

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.

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

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.

ArtBnB: Enjoy the Curated Comforts of Home
With easy highway access, and conveniently situated equidistance from Soulard, Lafayette Square, Tower Grove South, and Cherokee St, this custom designed space is not only an experience on its own, but a perfect base for exploring The Gateway City. Surround yourself with art, literature, and the homie comforts that set ArtBnB aside from staunch hotel chains. A lightly stocked kitchen, library, garden, patio, deck, grill, fire pit, wine rack, kennel, and toiletries are all included.

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!

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

Family Friendly Home Near Parks and Dining
Enjoy a relaxing experience at our conveniently located home in St. Peters. This 3 bedroom 2.5 home is fully stocked and ready for your family to visit. The neighborhood is quiet and within walking distance of a lovely park with walking trails, a playground, and ball fields. We are also minutes away from groceries, dining, and the St. Peters Recplex. We cannot wait to welcome you to our space for your next get away!
Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield

Perfect Getaway 3BR/3BA Home

Classy + Fun 4bd/1.5bth | Patio Dining | Game Room

Luxurious, spa-like retreat steps from Main St.

Fenced Yard - <1 mile from Purina - No Cleaning Fe

3+ acres, fast wi-fi, garage parking, Koi pond

Serene & Cozy Cabin + LAKE! Near Purina & SixFlags

4 Bedroom Cabin Retreat | Games & Pool Table

Cottage on Main Street- Low Cleaning Fee
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 holiday rentals in Chesterfield

Total holiday rentals
Explore 40 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $52 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
40 of Chesterfield holiday 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
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- Busch Stadium
- Central West End
- Six Flags St. Louis
- Enterprise Center
- Saint Louis Zoo
- St. Louis Aquarium at Union Station
- City Museum
- Missouri Botanical Garden
- Hidden Valley Ski Resort
- Gateway Arch National Park
- The Dome at America's Center
- Meramec State Park
- Castlewood State Park
- Cathedral Basilica of Saint Louis
- Gateway Arch
- Washington University in St Louis
- Saint Louis Science Center
- Forest Park
- Saint Louis University
- Stifel Theatre
- Missouri History Museum
- Soulard Farmers Market
- Laumeier Sculpture Park
- Fabulous Fox




