
Holiday houses in Chesterfield
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Top-rated holiday rentals in Chesterfield
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The Luxury Lodge in St. Charles
The Luxury Lodge is a Private Residence at Rear of Property with Private Keypad Door Entrance, Private Parking, Outdoor Deck, Dog Run Line and 1/2 acre Fenced Backyard. Kick back & relax in this serene, spotlessly clean, stylish luxury & country living in St. Charles, MO w/ Great Scenic View. Dog friendly, comfy Queen Size Bed, Love Seat, Queen Sleeper Sofa, Large Stone Fireplace, Huge Bathroom, Rain Shower, Private Powder Room, Large Screen TV, Cable & Streaming, Kitchenette, Fridge & Dresser.

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

Christmas Getaway in Historic 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.

Welcoming Downtown West Suite- King w/ Patio (223)
Enjoy your stay in one of our corporate housing retreats! Great housing option for anyone looking to stay in town for short or long-term periods of time! Fully equipped with all of your basic amenities and a few extras! We proudly boast a comfortable and enjoyable stay, all in the heart of PRIME Central West End St Louis! This location is great for anyone who wants to be located close to: - Barnes Jewish Hospital - SLU - Wash U - The Zoo - Nightlife - Downtown festivities and so much more!!

The Zen Den - Centrally Located, Calm and Tranquil
The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Cozy 1BR Apartment the "Ferner Flatette"
This unique, minimalistic apartment is located in the historic Benton Park neighborhood. A stroll away from restaurants, coffee shops, antique row and the park complete with lakes and walking paths. Recently renovated, its just minutes from downtown attractions: the Gateway Arch, Busch Stadium, Enterprise Center and Union Station Aquarium. Strict capacity of 2 persons. Window unit A/C, central heat. No pets, no smoking, no local guests. Government issued photo ID required prior to checkin.

Home Suite Home
A NEIGHBORHOOD home with a small town vibe. NO PARTIES tolerated!!!!! OPEN ALL PHOTOS TO READ PHOTO DETAILS. A PRIVATE BASEMENT SUITE with: PRIVATE Entry, Living Room, Bedroom, Full Bath, Kitchenette, Yard/Patio; walk to Historic Route 66, restaurants, coffee shops, shopping, churches, parks/playgrounds/trails; 10-20 minutes from Lambert Airport, Downtown STL, historic neighborhoods, and major attractions; and major US Highways. *SEARCH from 3915 Watson Rd, 63109 for travel distances.

*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.

Cozy Studio in Beautiful New Town St. Charles
Stay at this cozy studio centrally located in the amazing community of New Town St. Charles. New Town is a large scale new urbanist community built on the edge of suburbia. You never have to leave New Town with its walkability to restaurants, bars, a market, coffee shops, ice cream, food kiosk, canals, lakes, parks and tree lined streets. If you do leave its only a few miles from historic St. Charles Main street, The Streets of St. Charles, and 25 miles to Downtown St. Louis.

Modern, Cozy House In the Center of St. Louis Co.
This house sleeps 4 guests max! Enjoy a stylish stay at this centrally-located home. Modern amenities! 5 hospitals close by. Located in a safe, quiet area. The interior features 3 nice bedrooms & 2 full baths. There’s a front deck, high vaulted ceilings in the interior and great natural light. It’s 8 mins away from Creve Coeur trails. 20 mins from Central West End dining, 15 mins from Old Town St. Charles. Great location! 15 mins from Clayton.
Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield

Serenity Valley (No Cleaning Fee- No pets please)

Separate Entry Basement Apartment 1BR, 1BA

Honeymoon Suite at Camp Skullbone In The Woods

Luxurious, spa-like retreat steps from Main St.

Pacific Palace, super unique!

Weaver Guest House

Relaxing Oasis with Free Bottle of wine+brkfst

Maple Tree Enchanted Guest House 1 bedroom 2 beds
Frequently Asked Questions
Do house rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 house 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 house rentals in Chesterfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chesterfield?
Experience the best of Chesterfield with our house rentals, starting at about $50 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 wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, 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 30 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 280 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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- 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




