Best Vacation Homes in Chesterfield
1500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $165/Night
For 7 Nights US $1,155
269.1 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $152/Night
For 7 Nights US $1,066
US $81/Night
For 7 Nights US $567
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $124/Night
For 7 Nights US $868
1302.43 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $122/Night
For 7 Nights US $854
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $106/Night
For 7 Nights US $745
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
RV Rental
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $159/Night
For 7 Nights US $1,111
1000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $218/Night
For 7 Nights US $1,528
Chesterfield Luxury Rentals
9000 ft²
21 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Other
- Hot Tub
- Spa
- Fireplace/Heating
US $1,500/Night
For 7 Nights US $10,497
2673 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $522/Night
For 7 Nights US $3,657
900 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $504/Night
For 7 Nights US $3,531
1 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $397/Night
For 7 Nights US $2,782
1000 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $332/Night
For 7 Nights US $2,322
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $311/Night
For 7 Nights US $2,174
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $252/Night
For 7 Nights US $1,764
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $208/Night
For 7 Nights US $1,456
Chesterfield Pet Friendly Vacation Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $71/Night
For 7 Nights US $496
800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $122/Night
For 7 Nights US $856
Why Choose Rent By Owner for your Chesterfield Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chesterfield
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination can enhance your experience, as each season offers unique opportunities to enjoy the local atmosphere and natural beauty in Chesterfield, Illinois, USA.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, the region experiences warm weather ideal for outdoor activities and exploring local attractions. It's an excellent time to enjoy your stay in Chesterfield's inviting vacation rentals with pleasant daytime temperatures.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
Early Fall (September to October)
This season offers comfortable temperatures and vibrant autumn scenery, making it perfect for enjoying your vacation rental and the area's natural beauty. The region typically sees a surge in visitors seeking mild weather and scenic views.
Average Temperature Daytime: 70°F - 80°F - Nighttime: 50°F - 60°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and fewer crowds, providing a quiet retreat in your Chesterfield vacation rental. This is an ideal time for those seeking a peaceful escape and lower rates.
Average Temperature Daytime: 30°F - 45°F - Nighttime: 20°F - 30°F
Early Spring (March to April)
As the region transitions from winter, you can enjoy the early signs of spring with mild weather and blooming landscapes. Off-peak rates make it an attractive choice for budget-conscious travelers looking for a relaxing getaway.
Average Temperature Daytime: 50°F - 60°F - Nighttime: 35°F - 45°F
Weekly Weather Forecast for Chesterfield
How to Book Your Chesterfield Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chesterfield
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck for relaxing and entertaining.
- Take advantage of well-maintained gardens or landscaped yards that enhance your outdoor experience.
- Make the most of nearby parks or green spaces perfect for picnics, walking, or outdoor activities.
- Benefit from outdoor grilling areas or barbecue facilities to enjoy meals al fresco with loved ones.
- Use outdoor furniture such as loungers and dining sets designed for comfort and convenience.
- Explore available amenities like swimming pools or hot tubs for added relaxation during your stay.
- Discover outdoor recreational features like fire pits or fireplaces to gather with friends on cool evenings.
Top Attractions Around Chesterfield
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities and local attractions, making your stay in this region an engaging and enjoyable experience.
Family Activities
- Creekwood Park: You can enjoy a family picnic and outdoor play at this scenic park, perfect for relaxing in the local area.
- Chesterfield Family Center: Engage in activities like swimming, indoor sports, and fitness programs designed to keep the whole family active here.
- Nearby Nature Trails: Explore scenic walking and biking paths that wind through the region's natural beauty, ideal for outdoor adventures with kids.
- Local Community Events: Participate in seasonal festivals and family-friendly gatherings hosted regularly, offering fun experiences for all ages in the area.
Adult Activities
- Explore the Chesterfield Valley Premium Outlets: Enjoy a day of shopping at this popular outlet mall, offering great deals on designer brands in the heart of the region.
- Visit the St. Louis Premium Outlets: Take advantage of nearby outlet shopping just a short drive from here, perfect for fashion enthusiasts seeking savings.
- Discover local parks and outdoor spaces: Relax and unwind at nearby parks that offer scenic trails, picnic areas, and outdoor activities suitable for all ages.
- Experience regional dining options: Savor diverse cuisine at local restaurants and eateries that showcase the flavors distinctive to this part of Illinois.
Chesterfield Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's diverse culinary scene to enjoy authentic regional flavors during your stay.
- Visit Community Events: Check out local events and gatherings nearby to immerse yourself in the area's vibrant community atmosphere.
- Plan Outdoor Activities: Make the most of the region's parks and recreational spots for outdoor adventures right outside your vacation rental.
- Discover Unique Shopping Venues: Explore nearby shopping centers or boutiques to find one-of-a-kind souvenirs and local products for a memorable experience.
Transportation Options
- Interstate 64: This major highway provides quick access to the area, making it easy for you to travel by car to and from Chesterfield.
- St. Louis Lambert International Airport: Located nearby, the airport offers convenient flights if you're arriving from out of state or internationally.
- Metrolink Light Rail: The regional rail system connects this destination with the broader St. Louis metropolitan area, providing a reliable public transportation option.
- Local Bus Services: Public bus routes serve here, offering affordable and accessible transportation within the region for your convenience.
Local Customs Options
- Local Dining Etiquette: Respect for the region’s dining customs enhances your experience when enjoying traditional cuisine here.
- Community Events: Participating in neighborhood festivals and gatherings offers a authentic glimpse into local traditions.
- Historical Respect: Appreciating and observing historical sites and monuments reflects the region’s appreciation of its heritage.
- Greeting Customs: Friendly, informal greetings are common and appreciated when meeting residents in this area.
Chesterfield Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Chesterfield?
There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesterfield:
- Memorable Family experiences at The Castle of Palmyra.
- Country getaway at The Campground House.
- Luxury loft in the building from 1888
- Luxurious Otter Pointe
- The Carlinville Cottage
- Cozy studio located in small town America, Bunker Hill, IL.
- 3 bedroom 2 bath sleeps 6 comfortably with the option of 8 on a dual twin daybed
- Grand Victorian Carlinville home on Rt. 66.
- The Charleston Suite - A 2700 sq ft private upstairs suite, sleeps 8-10 people.
- Light Filled Loft on Town Square
2. Which vacation homes in Chesterfield are best for families?
If you are looking for a family-friendly vacation home in Chesterfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesterfield:
3. How many Rentbyowner vacation rentals are available in Chesterfield?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 29 in the Chesterfield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chesterfield.
4. What is the cancellation policy for vacation rentals in Chesterfield, Illinois?
Cancellation policies vary depending on the property listing. It’s recommended to review the specific rental’s policy before booking or contact the host directly for detailed information.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning charges, service fees, or security deposits may apply. Please read the listing details carefully or reach out to the owner to clarify all costs involved.
6. What amenities are typically included in vacation rentals in this area?
Most properties offer amenities like Wi-Fi, parking, kitchen facilities, and laundry. To confirm available amenities, review the property description or contact the host ahead of your stay.
7. How do I ensure my reservation is secure and confirmed?
Reservations are secured through the booking platform once you complete the payment process. For added assurance, verify the host’s profile and read reviews from previous guests before confirming your reservation.
8. What is the check-in and check-out process for vacation rentals in the region?
Check-in and check-out procedures depend on each property’s policy. Details are usually provided after booking, but you can also communicate directly with the host for specific instructions.
