Best Vacation Homes in Chester
630 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $143/Night
For 7 Nights US $998
13 Guests
9 Bedrooms
3 Bathrooms
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $177/Night
For 7 Nights US $1,239
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Balcony/Terrace
- Breakfast
- Parking
US $160/Night
For 7 Nights US $1,123
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $172/Night
For 7 Nights US $1,205
613.54 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Parking
- Internet
US $99/Night
For 7 Nights US $693
8 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $201/Night
For 7 Nights US $1,410
784 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Parking
US $156/Night
For 7 Nights US $1,094
1200 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,589
Chester Luxury Rentals
6800 ft²
18 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,595/Night
For 7 Nights US $11,164
4500 ft²
23 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,521/Night
For 7 Nights US $10,646
6802.79 ft²
18 Guests
7 Bedrooms
4 Bathrooms
Free Cancellation
House
- Private Pool
- Private Beach
- Oceanfront
US $1,413/Night
For 7 Nights US $9,891
3100 ft²
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,260/Night
For 7 Nights US $8,818
3498 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $870/Night
For 7 Nights US $6,092
1 Bedroom
1 Bathroom
Couples Retreat
House
- Parking
- Internet
- Child Friendly
US $858/Night
For 7 Nights US $6,005
3498.27 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Air Conditioner
US $622/Night
For 7 Nights US $4,356
US $602/Night
For 7 Nights US $4,214
Chester Pet Friendly Vacation Rentals
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $222/Night
For 7 Nights US $1,551
904.17 ft²
4 Guests
7 Bedrooms
1 Bathroom
Pet Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $204/Night
For 7 Nights US $1,428
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $287/Night
For 7 Nights US $2,008
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $529/Night
For 7 Nights US $3,706
8 Guests
3 Bedrooms
3 Bathrooms
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $126/Night
For 7 Nights US $882
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $212/Night
For 7 Nights US $1,482
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
For 7 Nights US $1,711
1500 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $391/Night
For 7 Nights US $2,739
Chester Large Vacation Homes
1980 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $596/Night
For 7 Nights US $4,173
3700 ft²
12 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Cabin
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,169/Night
For 7 Nights US $8,186
6000 ft²
16 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
Other
- Private Pool
- Pool
- Balcony/Terrace
US $1,000/Night
For 7 Nights US $7,000
Why Choose Rent By Owner for your Chester 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 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
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
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
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
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
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.
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.
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
Memorial Hospital
Elzie C. Segar Memorial Park
Popeye Museum
Chester Skating Rink
Kaskaskia Bell
Mary's River Covered Bridge
Saint Mary
Bremen
Prairie du Rocher
Sparta
Misselhorn Art Gallery
Baldwin
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:
- 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
- Cottage w/Yard, Walk to Historic Attractions
- ⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed.nSleeps 4
- Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town
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 2026 is over 119 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.
Chester Top Rated Vacation Rentals
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $118/Night
For 7 Nights US $825
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $111/Night
For 7 Nights US $777
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $163/Night
For 7 Nights US $1,138
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $82/Night
For 7 Nights US $572
US $75/Night
For 7 Nights US $522
US $77/Night
For 7 Nights US $536
US $82/Night
For 7 Nights US $571
US $92/Night
For 7 Nights US $647
