Discover Your Perfect Winslow Vacation Homes

Why Choose Rent By Owner for your Winslow 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 Winslow

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, especially when considering seasonal weather patterns and local events in this destination's charming region.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the region's scenic landscapes and outdoor activities.

Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
autumn
Fall (September to November)

The fall offers stunning foliage colors and a crisp climate, attracting visitors who appreciate vibrant scenery and comfortable outdoor conditions.

Average Temperature Daytime: 60°F - 70°F - Nighttime: 40°F - 50°F

Off-Season Highlights

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Winter (December to February)

In winter, the region experiences colder temperatures and quieter surroundings, providing a peaceful setting for cozy stays and seasonal activities.

Average Temperature Daytime: 20°F - 35°F - Nighttime: 10°F - 20°F
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Spring (March to May)

Spring brings milder weather and budding landscapes, offering a quieter time for those seeking less crowded accommodations and scenic tranquility.

Average Temperature Daytime: 45°F - 55°F - Nighttime: 30°F - 40°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 outdoor seating areas such as patios or decks where you can relax and take in the fresh air.
  • Benefit from access to spacious yards or gardens, perfect for outdoor activities or picnics.
  • Make the most of private or shared barbecue grills to experience local flavors during your stay.
  • Seek out properties featuring outdoor fire pits, ideal for cozy evenings in a scenic setting.
  • Explore nearby hiking and walking trails accessible directly from your rental property.
  • Take advantage of outdoor dining setups, allowing you to enjoy meals amidst the natural surroundings.
  • Look for rentals with versatile outdoor furniture for lounging and entertaining in the region's charming climate.

Top Attractions Around Winslow

What attractions are nearby?

While staying nearby, you can enjoy exploring scenic parks, engaging in outdoor activities, and discovering local cultural sites that showcase the charm of the region.

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Family Activities

  • Waterville Opera House: Experience local culture and family-friendly performances at this historic venue, right in the heart of the region.
  • Colby College Museum of Art: Enjoy exploring a rich collection of artwork suitable for visitors of all ages, making it an educational outing here.
  • Laurel Hill Cemetery: Take a scenic walk through this picturesque cemetery that offers tranquility and historical insights into the area's past.
  • Winthis Game Arcade: Have fun with your loved ones at this classic arcade featuring a variety of games perfect for family entertainment in Waterville.
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Adult Activities

  • Velvet Ice Cream Tasting: Indulge in local flavors at popular ice cream parlors that showcase the region's sweet heritage.
  • Historic Downtown Walks: Explore charming streets lined with historic architecture, shops, and cafes reflecting this area's rich cultural history.
  • Maine State Museum Visits: Discover the area's history and natural beauty through engaging exhibits at the Maine State Museum.
  • Paddleboarding on nearby lakes: Enjoy relaxing paddleboarding adventures on tranquil waters that surround here, offering scenic views and outdoor fun.

Other Places to Stay in Winslow, ME

Fort Halifax
Fort Halifax Vacation Rentals
More Places to Stay Near Winslow

Winslow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Landmarks: Take time to discover the region’s historic sites and scenic spots to enrich your experience of this charming destination.
  • Plan for Outdoor Activities: Make the most of the area's natural beauty by scheduling outdoor adventures like hiking or kayaking during your stay.
  • Visit Nearby Dining Experiences: Savor regional cuisine at local eateries to get a true taste of the area’s culinary culture.
  • Book in Advance: Secure your preferred vacation rentals early to ensure a seamless and stress-free visit to this popular travel destination.

Transportation Options

  • Waterville Area Transit (WAT): This regional bus service offers convenient transportation around this part of Maine, making it easy to explore the region without a car.
  • Amtrak Passenger Service: The nearby stations connect travelers to major cities along the East Coast, providing a reliable rail option for exploring the wider area.
  • Local Taxi and Rideshare Services: Taxis and rideshare companies like Uber and Lyft are readily available here, offering flexible and on-demand travel around the city and its surroundings.
  • Private Car Rentals: Several car rental agencies operate in this destination, giving you the freedom to explore Waterville and the region at your own pace during your stay.

Local Customs Options

  • Native American Heritage: Respect for the region's indigenous roots is a significant aspect of local customs, reflected in community events and educational initiatives.
  • Seasonal Festivities: Celebrating each season with unique events, such as fall foliage festivals and winter holiday traditions, enhances the area's welcoming atmosphere.
  • Community Hospitality: Visitors find that engaging with residents through local markets and events exemplifies the warm, neighborly spirit characteristic of here.

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. 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:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 47 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. 

4. What is the cancellation policy for vacation rentals in this area?

The cancellation policies vary depending on the specific property. It is recommended to review the cancellation details listed on the property page or contact the host directly to understand the terms applicable during your booking.

5. How do I confirm my reservation and what are the payment options?

Reservations are confirmed after completing the booking process on the site, which includes selecting your dates and making a secure payment. Payment methods typically include credit cards and other accepted online payment options; details will be provided during the booking.

6. Are there any additional fees or deposits required when booking here?

Additional fees such as cleaning fees, service charges, or security deposits may apply depending on the property. These details are usually outlined on the listing page, so it’s advisable to review them carefully before finalizing your reservation.

7. What amenities and features are typically included in these vacation rentals?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking. The exact features vary, so it’s best to check the listing's description and photos to ensure the rental meets your needs.

8. How do I get in touch with the property owner if I have questions or special requests?

Contact information for the property owner or host is available on the listing page. You can reach out directly through the messaging system to ask questions or discuss any specific requirements for your stay.