Why Choose Rent By Owner for your Olympia Fields Winter Rental?
What makes our Winter Rental special?
Best Times to Visit Olympia Fields
When should you plan your Winter Rental stay?
Choosing the ideal time to enjoy your winter rentals here can enhance your experience, as the region offers distinct advantages during specific months when the area’s charm and comfort are at their peak for visitors seeking a cozy and convenient getaway.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather ideal for outdoor activities and exploring the region's natural beauty.
Fall (September to November)
The fall season offers crisp air and vibrant foliage, perfect for experiencing the area's scenic landscapes.
Off-Season Highlights
Winter (December to February)
Winter is a tranquil time to visit, with cooler temperatures providing a cozy atmosphere for your stay.
Spring (March to May)
Spring signals renewal with milder weather and blooming scenery, offering a peaceful retreat during these months.
Weekly Weather Forecast for Olympia Fields
How to Book Your Olympia Fields Winter Rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Olympia Fields
Common Winter Rental Amenities
What amenities can you expect?
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 patio or deck perfect for relaxing during your winter stay.
- Take advantage of well-maintained landscaped gardens that add to the scenic beauty of your accommodation.
- Make use of a spacious yard ideal for outdoor activities or simply soaking in the fresh air.
- If available, unwind by a fire pit during chilly evenings for cozy gatherings with family or friends.
- Benefit from access to outdoor dining areas, making it easy to enjoy meals outdoors in the fresh winter air.
- Explore nearby walking trails or parks accessible directly from your rental, offering scenic winter views.
- Some properties might feature outdoor recreational amenities such as a basketball hoop or sports court for active fun.
Top Attractions Around Olympia Fields
What attractions are nearby?
Within this area, you can enjoy a variety of activities that showcase the local culture and natural beauty, providing an enriching experience just minutes from your winter rentals in Olympia Fields, Illinois.
Family Activities
- Olympia Fields Park Enjoy a family picnic or outdoor games in this spacious park, which offers a safe and scenic environment for all ages.
- Golf Learning Center Introduce the kids to golf at this family-friendly facility that provides lessons and practice areas suitable for beginners and experienced players alike.
- Bike Trails along the Region Explore the area’s scenic bike trails together, offering an active way to discover the local natural beauty during your stay.
- Community Recreation Center Participate in seasonal programs, indoor activities, or fitness classes designed specifically for families looking to stay active and entertained during winter visits.
Adult Activities
- Golf at Olympia Fields Country Club: Experience world-class golf on the renowned course nestled within this destination, perfect for a relaxing day amidst scenic landscapes.
- Theatre and Performing Arts: Enjoy captivating performances and cultural events that showcase the vibrant arts scene in the area, ideal for an evening escape.
- Local Shopping and Dining: Explore diverse shopping options and culinary delights at nearby centers, providing a great way to indulge during your winter stay here.
- Nature Walks and Parks: Take advantage of serene walking trails and parks in the region, offering peaceful spots to unwind and enjoy the outdoor winter scenery.
Other Places to Stay in Olympia Fields, IL
Olympia Fields Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Book your winter rental early to secure the best properties and ensure availability during peak travel seasons in this area.
- Explore Local Dining: Take advantage of the region’s dining options to enjoy authentic flavors without traveling far from your accommodation.
- Utilize Nearby Transportation: Make use of local transit services or rental vehicles to conveniently explore the surrounding neighborhoods and attractions.
- Check Amenities: Review the amenities included with your winter rental to maximize comfort and convenience during your stay here.
Transportation Options
- Chicago O'Hare International Airport As a major transportation hub in the region, it offers numerous domestic and international flights to connect you conveniently to this destination and beyond.
- Metra Electric District This commuter rail service provides direct access from the nearby city to the area, making it a reliable option for daily travel or excursions.
- Local Bus Services Regional bus routes serve the vicinity well, allowing you to explore the area and reach nearby attractions with ease during your stay.
- Taxi & Ride-Sharing Services Convenient and flexible, these options are readily available to help you navigate the region comfortably, especially when traveling with luggage or during winter conditions.
Local Customs Options
- Respect for the Quiet Hours: It is customary here to observe designated quiet hours, ensuring a peaceful environment for residents and visitors alike.
- Community Sportsmanship: Participating in or supporting local sports events reflects the area's emphasis on friendly competition and community spirit.
- Celebration of Local Holidays: Embracing traditional holidays with family gatherings and community events highlights the area's cultural values.
- Green Initiatives: Eco-friendly practices, such as recycling and conserving energy, are valued by locals, making sustainable living common during your stay.
Frequently Asked Questions About Olympia Fields Winter Rentals
1. What are the top Winter Rentals in Olympia Fields?
There are a lot of options in Olympia Fields. If you plan on staying in the Olympia Fields area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Olympia Fields:
- Homewood Rental - Cherrywood Ln
- Glamping Yurt & RV/Game Room/Pool, Outdoor Jacuzzi, Sauna, Mini Golf, Chickens!
- Country Club Hills Rentaln
- Country Club Hills Rentaln
- Homewood - Cherrywood Ln
- Flossmoor Rental
- Homewood FHS Rental - Cherrywood Ln
- Richton Park Rental
- Near Casino with Arcade LCP Collection
- Escape to The Hills: Spacious 3-Bed Retreat with Family & Game Rooms - Sleeps 8!
2. How many Winter Rentals are available in Olympia Fields?
Currently, the total number of properties listed by RBO in 2026 is over 37 in the Olympia Fields area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Olympia Fields.


























