Discover Your Perfect Chester Vacation Homes

Chester Luxury Rentals

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Find More Chester Villas, Resorts, & Rentals on BedroomVillas

Why Choose Rent By Owner for your Chester Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Vacation Rentals stay?

Choosing the right time to visit here ensures you can enjoy the region’s unique charm and make the most of your stay in Chester, Illinois, USA, whether you're seeking lively seasonal events or peaceful off-peak moments.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the region experiences warm weather and blossoming landscapes, making it an ideal time for outdoor activities and exploring local attractions.

Average Temperature Daytime: 75°F - Nighttime: 55°F
autumn
Early Fall (September to October)

This season offers pleasant temperatures and vibrant fall foliage, perfect for enjoying the scenic views and outdoor excursions in the area.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and quieter surroundings, providing a peaceful setting for those seeking solitude and cozy getaways.

Average Temperature Daytime: 40°F - Nighttime: 25°F
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Late Fall to Early Winter (November)

As nature prepares for winter, this shoulder season features fewer visitors and mild temperatures, allowing you to enjoy the region's tranquility.

Average Temperature Daytime: 55°F - Nighttime: 40°F

Weekly Weather Forecast for Chester

How to Book Your Chester 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 Chester

More Top-Rated Vacation Rentals in Chester Area

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 outdoor seating areas perfect for relaxing and taking in the scenic views surrounding your stay.
  • Take advantage of private or shared patios and decks to unwind outdoors with family or friends.
  • Make the most of spacious yards or gardens ideal for outdoor activities or children’s playtime.
  • Benefit from access to outdoor grills or barbecue facilities to host delightful cookouts.
  • Relax by a swimming pool or hot tub, perfect for unwinding after exploring the area's attractions.
  • Explore nearby walking or biking trails that offer a great way to experience the natural beauty of this destination.
  • Utilize available outdoor dining spaces to enjoy meals while soaking in the fresh air and views of the region.

Top Attractions Around Chester

What attractions are nearby?

Explore a variety of outdoor activities and local attractions just moments from your vacation rentals in Chester, Illinois, USA, offering you the perfect opportunity to enjoy the area's natural beauty and cultural sights during your stay.

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Family Activities

  • Chester City Park: Enjoy a family picnic, playground fun, and scenic walking trails at this popular park in the area.
  • Fox Creek Golf Course: Tee off on this family-friendly golf course that offers a relaxed atmosphere and beautiful views near Chester.
  • The Great River Road: Take a leisurely drive or bike ride along this scenic route to explore breathtaking river views and natural beauty.
  • Heritage Museum of Southern Illinois: Discover local history and interactive exhibits that appeal to children and adults alike here in Chester.
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Adult Activities

  • Chester Area Golf Courses: Enjoy a relaxing day on the greens at some of the region’s top golf courses, perfect for unwinding while taking in scenic views.
  • The Trail of Tears State Park: Explore this historic park with its tranquil trails and picturesque landscapes, ideal for outdoor enthusiasts seeking a peaceful retreat.
  • Downtown Chester Historic Walking Tour: Discover the area's rich heritage by strolling through downtown Chester, where historic architecture and local landmarks tell compelling stories.
  • Local Wineries: Sample regional wines at nearby wineries, offering a sophisticated way to enjoy the area’s agricultural charm and scenic vineyards.

Other Places to Stay in Chester, IL

Popeye Museum
Popeye Museum Vacation Rentals
Memorial Hospital
Memorial Hospital Vacation Rentals
Elzie C. Segar Memorial Park
Elzie C. Segar Memorial Park Vacation Rentals
Kaskaskia Bell
Kaskaskia Bell Vacation Rentals
Chester Skating Rink
Chester Skating Rink Vacation Rentals
Mary's River Covered Bridge
Mary's River Covered Bridge Vacation Rentals
Saint Mary
Saint Mary Vacation Rentals
Prairie du Rocher
Prairie du Rocher Vacation Rentals
Bremen
Bremen Vacation Rentals
Sparta
Sparta Vacation Rentals
Sparta Country Club
Sparta Country Club Vacation Rentals
Baldwin
Baldwin Vacation Rentals
More Places to Stay Near Chester

Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local attractions and outdoor activities: Take advantage of the region’s scenic parks and outdoor spaces to fully enjoy the natural beauty surrounding your vacation rental in Chester.
  • Visit nearby dining establishments and local markets: Savor authentic regional cuisine and pick up fresh ingredients to enhance your stay here.
  • Plan day trips to nearby towns and points of interest: Use Chester as a convenient base to discover the area's hidden gems and cultural sites.
  • Book your accommodations early: Secure your preferred vacation rentals in this destination ahead of time to ensure a seamless and enjoyable experience.

Transportation Options

  • Car Rentals: You can easily rent a vehicle in the area to explore Chester and its surrounding attractions at your own pace.
  • Public Transit: The region offers accessible bus services that connect you with key destinations nearby, making local travel convenient.
  • Taxi and Rideshare Services: Taxis and ridesharing options are available here, providing quick and reliable transportation throughout Chester.
  • Bicycle Rentals: For a scenic and eco-friendly way to tour the area, bicycle rentals are a popular choice among visitors seeking outdoor exploration.

Local Customs Options

  • Local Fishing Traditions: Engaging in fishing along the Mississippi River is a cherished custom, reflecting the region's rich connection to its waterways.
  • Southern Hospitality: Visitors often notice the warm welcomes and courteous manners that are integral to the area's friendly community spirit.
  • Historic Preservation: Respect for the area's historical sites and customs is evident through local efforts to maintain Chester’s unique heritage.
  • Easter Parades and Festivities: Celebrating seasonal holidays with community parades and events highlights the region’s vibrant local traditions.

Frequently Asked Questions About Chester?

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:

2. Which vacation homes in Chester are best for families?

If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:

3. How many Rentbyowner vacation rentals are available in Chester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 109 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. 

4. What is the cancellation policy for vacation rentals in Chester, Illinois?

Cancellation policies vary by listing, so it’s important to review the specific terms and conditions provided in the property details or contact the owner directly for clarification.

5. Are there any additional fees I should be aware of when booking a vacation rental in the area?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing. Be sure to read the full description or reach out to the host for detailed fee information.

6. How do I confirm my reservation and what steps are involved in booking a vacation rental here?

Booking is completed through the platform by selecting your dates, reviewing the listing details, and submitting your reservation request. You may need to communicate with the owner for confirmation or special arrangements.

7. Is there a minimum stay requirement for vacation rentals in this destination?

Minimum stay requirements can differ depending on the property. Check the specific listing details or contact the owner to clarify the minimum number of nights needed for your preferred dates.

8. What amenities are typically included in Chester vacation rentals and how do I find listings that meet my needs?

Amenities vary by property, but you can filter search results based on your preferences such as Wi-Fi, parking, or pet-friendliness. Review each listing carefully to ensure it offers the features that are important to you.