Discover Your Perfect Winslow Vacation Homes

Winslow Luxury Rentals

See More Winslow Luxury Vacation Rentals
Find More Winslow Villas, Resorts, & Rentals on BedroomVillas

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

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Winslow

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can significantly enhance your experience, as the best seasons for exploring this destination often depend on your preferred weather and outdoor activities in the region.

Peak Season Highlights

summer
Summer (June to August)

Experience the warm weather and longer daylight hours that make this time ideal for outdoor activities and exploring the region's natural beauty.

Average Temperature Daytime: around 80°F - Nighttime: around 60°F
autumn
Fall (September to November)

Enjoy the vibrant fall foliage and cooler temperatures, perfect for scenic drives and cozy evenings in your vacation rentals.

Average Temperature Daytime: about 70°F - Nighttime: around 45°F

Off-Season Highlights

image
Winter (December to February)

During this quieter season, you can find more peaceful surroundings and potentially better rates on your accommodations here.

Average Temperature Daytime: roughly 30°F - Nighttime: close to 15°F
image
Early Spring (March to April)

As the area transitions from winter to spring, expect fewer crowds while enjoying the early signs of new growth and milder weather.

Average Temperature Daytime: around 50°F - Nighttime: about 30°F

Weekly Weather Forecast for Winslow

How to Book Your Winslow 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 Winslow

More Top-Rated Vacation Rentals in Winslow 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 a spacious outdoor patio or deck for relaxing and dining under the open sky.
  • Take advantage of lush, private gardens or landscaped yards perfect for outdoor activities.
  • Make use of community or private swimming pools, ideal for cooling off during warm days.
  • Benefit from well-maintained fire pits or outdoor fireplaces for cozy evenings with family and friends.
  • Experience outdoor recreation with access to fishing spots or nearby lakes.
  • Utilize dedicated outdoor seating areas for enjoying scenic views of the surrounding region.
  • Explore nearby walking or biking trails that provide immersive outdoor experiences here in the area.

Top Attractions Around Winslow

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities and local attractions that highlight the area's natural beauty and community spirit, making your stay truly memorable.

image
image

Family Activities

  • Winslow Family Fun Center: Enjoy a day of arcade games, mini-golf, and kiddie rides perfect for family bonding in the region's popular entertainment spot.
  • Highland Community College Planetarium: Explore the wonders of the universe through engaging shows suitable for children and adults alike, right here in this destination.
  • Lake Park: Spend quality time outdoors by fishing, picnicking, or taking leisurely walks along scenic trails in this picturesque park setting within the area.
  • Historic Downtown Winslow: Discover local shops, enjoy family-friendly dining, and immerse yourself in the area's charming small-town atmosphere with plenty of opportunities for exploration.
image

Adult Activities

  • Winslow Historical Museum: Explore local history through engaging exhibits that offer a glimpse into the area's rich past and cultural heritage.
  • Winslow Nature Trails: Enjoy walking or biking along scenic trails that showcase the natural beauty of this region’s landscape.
  • Fishing at Winslow Lake: Spend a relaxing day casting lines in the tranquil waters and experiencing the outdoor serenity that this area has to offer.
  • Bird Watching Opportunities: Discover diverse bird species by visiting local parks and reserves, perfect for nature enthusiasts seeking quiet moments here.

Winslow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Make the most of your stay by discovering the area’s local attractions and cultural sites to enrich your experience here.
  • Plan Ahead for Amenities: Book a vacation rental with the amenities you need in advance to ensure a comfortable and convenient visit.
  • Engage with the Community: Take time to engage with locals and participate in community events to truly immerse yourself in this destination.
  • Travel Off-Peak: Consider visiting during off-peak seasons to enjoy fewer crowds and better rates on your vacation rentals in this region.

Transportation Options

  • Winslow Amtrak Station: Offers convenient train service connecting you to major cities and the region, making travel flexible and straightforward.
  • Local Bus Services: Provides budget-friendly transportation options within the area, ideal for exploring Winslow's nearby attractions and amenities.
  • Taxi and Rideshare Options: Available for quick and private transfers around town or to neighboring regions, ensuring comfort and convenience during your stay.
  • Car Rentals: Enables you to explore the wider region at your own pace, with rental agencies conveniently located nearby for easy access.

Local Customs Options

  • Local Craftsmanship: Here, you can observe the region's rich tradition of craftsmanship reflected in local handmade goods and artisan work.
  • Community Events: Participating in seasonal festivals and gatherings offers a unique glimpse into the area's cherished customs and social life.
  • Religious Traditions: The community celebrates various religious events with reverence, showcasing longstanding spiritual practices.
  • Food Customs: Enjoying traditional regional cuisine provides an authentic taste of the area's culinary heritage during your stay.

Frequently Asked Questions About Winslow?

1. What are the top vacation rentals in Winslow?

There are a lot of options in Winslow. If you plan on staying in the Winslow area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winslow:

2. How many vacation rentals have private pools in Winslow?

There are 2 vacation rentals with private pools near Winslow. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Winslow are best for families?

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

4. How many Rentbyowner vacation rentals are available in Winslow?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 61 in the Winslow 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 Winslow. 

5. What is the cancellation policy for vacation rentals in Winslow, Illinois?

The cancellation policy varies depending on the host and specific property. It's best to review the details listed in the rental agreement or contact the owner directly to understand the terms and any potential fees before booking.

6. Are there any specific check-in and check-out times I should be aware of in Winslow vacation rentals?

Check-in and check-out times are typically specified in the property listing. To ensure a smooth stay, confirm these times with the owner prior to your arrival, as they can vary between properties.

7. How do I contact the property owner if I have questions during my stay in this region?

Contact information is usually provided in the property listing or reservation confirmation. Reach out to the owner through the platform’s messaging system for any inquiries or assistance needed during your stay.

8. Are amenities like Wi-Fi and parking included at vacation rentals here?

Most listings specify included amenities such as Wi-Fi and parking. To avoid surprises, review the property details carefully or ask the owner directly about available features before confirming your reservation.

9. What should I know about local regulations or restrictions when staying in vacation rentals in this area?

Local rules and restrictions may apply to short-term stays, including noise ordinances or occupancy limits. It's recommended to read the property description thoroughly and consult with the owner to ensure compliance with all local regulations.