Chester Rentals by Owner
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- Pet Friendly
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Apartment
- Air Conditioner
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- Security/Safety
House
- Air Conditioner
- Parking
- TV
Apartment
- Air Conditioner
- Parking
- Pet Friendly
Apartment
- Air Conditioner
- Parking
- Pet Friendly
Apartment
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Chester vacation rental?
What makes our Rentals by Owner 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 Chester
When should you plan your Rentals by Owner stay?
Timing your vacation in this area can enhance your experience, so consider visiting during the region's most favorable seasons to enjoy ideal weather and local events when booking through Rent By Owner in Chester, Illinois.
Peak Season Highlights
Spring (March to May)
During springtime, you can enjoy the pleasant weather and blooming landscapes in this area, making it a popular time for visitors seeking outdoor activities and scenic views.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Autumn brings cooler temperatures and vibrant foliage, attracting travelers who want to experience the region's picturesque scenery and comfortable climate.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In winter, the area's quieter atmosphere allows for a peaceful retreat, though you should prepare for colder temperatures and possible seasonal closures.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Summer (June to August)
While summer sees increased activity, the hot and humid weather may limit some outdoor pursuits, making it an ideal time for those seeking less crowded accommodations by owner.
Average Temperature Daytime: 85°F to 95°F - Nighttime: 65°F to 75°F
Weekly Weather Forecast for Chester
How to Book Your Chester vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. 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 Chester
Common Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner 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 outdoor seating areas, perfect for relaxing or dining al fresco amid the scenic surroundings.
- Take advantage of a private backyard or garden space to unwind during your stay.
- Make use of a spacious deck or patio ideal for entertaining guests or enjoying the sunset views.
- Benefit from easy access to nearby parks or green spaces for outdoor activities and exploration.
- Utilize outdoor grills or picnic areas available for preparing meals while soaking up the local atmosphere.
- Discover a charming porch or veranda that offers a peaceful spot to read or enjoy morning coffee.
- Some rentals may include recreational features such as a fire pit or outdoor fireplace for cozy evenings outside.
Top Attractions Around Chester
What attractions are nearby?
While staying here, you'll find a variety of nearby activities to enjoy in Chester, Illinois, providing a perfect balance of relaxation and exploration for your visit to this charming destination.
Family Activities
- Chester City Park: Enjoy a family picnic or take a leisurely stroll through the scenic grounds in this welcoming city park.
- Mississippi River Levee: Explore the levee for beautiful river views and family-friendly walking trails along the region's iconic waterway.
- Chester Heritage Center: Discover local history and culture together while engaging with exhibits that provide an educational experience for all ages.
- Local Nature Trails: Venture into nearby nature trails perfect for hiking, bird watching, and outdoor adventures suited for families visiting here.
Adult Activities
- Visit the Chester Visitor Center: Explore the local history and gather insider tips to enhance your stay in this charming region.
- Explore the Mississippi River Bluffs: Enjoy scenic views and outdoor activities along the riverbanks that define the area's natural beauty.
- Discover local wineries and breweries: Sample regional flavors at nearby establishments that showcase the area's vibrant craft beverage scene.
- Enjoy a round of golf at Chester Golf Course: Play on well-maintained fairways while taking in picturesque surroundings unique to this part of Illinois.
Other Places to Stay in Chester, IL
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take the time to sample regional specialties at nearby eateries to truly immerse yourself in the area's culinary scene during your stay.
- Visit natural attractions: Discover the region's scenic parks and outdoor spaces to enjoy relaxing moments and scenic views away from the urban bustle.
- Plan your activities ahead: Booking tours or experiences in advance ensures you make the most of your visit and avoid missing out on popular local offerings.
- Communicate with your host: Sharing your interests and questions with your rental host can provide personalized tips that enhance your experience here.
Transportation Options
- Chester Municipal Airport: This airport offers convenient regional flights, making it easier for you to arrive in the area with minimal hassle.
- Local taxi services: Reliable taxi providers in the region ensure smooth door-to-door transportation for your travel needs within and around Chester.
- Car rental outlets: Several car rental agencies are available nearby, giving you the flexibility to explore the surrounding attractions at your own pace.
- Public transit options: Bus services connect Chester with neighboring cities and key points of interest, providing an affordable transportation choice during your stay.
Local Customs Options
- Southern Hospitality: You’ll notice a warm and welcoming attitude among locals when you visit, reflecting the region’s friendly community spirit.
- During local celebrations, it’s common to see colorful decorations and displays that showcase the area's rich cultural heritage and pride.
- Community Events: Participating in or observing neighborhood gatherings and festivals offers insight into this destination’s close-knit traditions.
- Local Cuisine Etiquette: When dining here, it’s customary to enjoy generous portions and appreciate the communal aspect of shared meals, which is a cherished custom in the area.
Frequently Asked Questions About Chester Rentals by Owner
1. What are the top vacation rentals in Chester?
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester:
- Beautiful Modern Loft In Wine Country!
- Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
- Secluded Private Cabin with Pool, hot tub, fireplace & so much more
- The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
- Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
- "Little Brick House on Main (1865)”
- Lodge at the Longbranch next to the Longbranch Saloon
- Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
- Log Lodge - Secluded - Private Pool - Game Room - WiFi - 1 Hr South of St.Louis
- 'The Brewer Guesthouse' Tiny Home w/Patio & Yard!
2. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 70 in the Chester 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 Chester.
3. What is the cancellation policy for a rental by owner in the area?
The cancellation policy varies depending on the specific listing. You should review the details provided in the rental listing or contact the owner directly to understand the terms and any potential fees.
4. How do I ensure the rental property in this region meets my needs before booking?
You can review the property description, amenities, and photos listed online. Additionally, reaching out to the owner for clarification or specific questions helps ensure the rental aligns with your expectations.
5. Are there any house rules I need to be aware of when staying at a rental by owner here?
Yes, each rental may have its own house rules, such as restrictions on smoking, pets, or noise levels. These are typically outlined in the listing, or you can ask the owner directly to clarify.
6. What should I know about check-in and check-out procedures for rentals in this destination?
Check-in and check-out instructions are usually included in the listing or communicated by the owner. It’s advisable to confirm these details ahead of your arrival to ensure a smooth stay.
7. How can I confirm the availability of a rental property in this area before booking?
Availability can be checked directly through the listing on Rent By Owner. If you have specific dates in mind, contacting the owner for confirmation is also recommended.
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