Discover Your Perfect Windsor Vacation Homes

Why Choose Rent By Owner for your Windsor 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 Windsor

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can greatly enhance your experience, as each season offers its own unique charm within this region known for its peaceful countryside and scenic beauty.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the area experiences warm temperatures and longer daylight hours, making it ideal for outdoor activities and exploring the scenic surroundings.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 50°F to 55°F
autumn
Early Fall (September to October)

As the foliage begins to change, you can enjoy the crisp air and vibrant colors, creating a picturesque setting perfect for relaxing and sightseeing.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

The region quiets down during the winter months, offering a peaceful retreat with potential for snowy landscapes and cozy accommodations.

Average Temperature Daytime: 30°F to 35°F - Nighttime: 15°F to 20°F
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Late Fall (November) and Early Spring (March)

These shoulder months feature cooler weather and fewer visitors, providing a tranquil atmosphere for those seeking solitude and lower rates on vacation rentals.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 35°F

Weekly Weather Forecast for Windsor

How to Book Your Windsor 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 Windsor

More Top-Rated Vacation Rentals in Windsor 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 dining with a furnished patio or picnic area, perfect for meals amidst the scenic surroundings.
  • Take advantage of a spacious backyard, ideal for relaxing, playing, or barbecuing during your stay.
  • Make use of a private or shared waterfront access for boating, fishing, or enjoying views of nearby lakes or rivers.
  • Relax in a hammock or lounge chairs set up in a tranquil outdoor space, allowing you to unwind in nature.
  • Explore walking or hiking trails directly from the property, providing easy access to local natural scenery.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars with family and friends.
  • Benefit from ample parking areas suitable for RVs, boats, or multiple vehicles, making outdoor adventures more convenient.

Top Attractions Around Windsor

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as hiking and exploring scenic parks just a short drive from your vacation rental in Windsor, Maine, providing the perfect opportunity to immerse yourself in the natural beauty of the region.

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Family Activities

  • Windsor Fairgrounds: Experience local culture and family-friendly events at the Windsor Fairgrounds, perfect for community gatherings and seasonal festivals.
  • Windsor Historical Society Museum: Discover the area's rich history through interactive exhibits and engaging tours suitable for visitors of all ages.
  • Pleasant River Waterfront Park: Enjoy a leisurely day outdoors by the water with picnic areas, walking trails, and scenic views in this tranquil setting.
  • Local Farms and Orchards: Visit nearby farms and orchards to pick fresh produce or experience farm-to-table activities that highlight the region’s agricultural charm.
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Adult Activities

  • Windsor Historical Society: Dive into the rich local heritage by exploring this engaging museum that offers insight into the area's history and culture.
  • Maine State Pier: Enjoy a relaxing stroll along the pier, taking in scenic views of the water and the surrounding natural beauty unique to this region.
  • Local Wineries and Breweries: Experience the region’s vibrant craft beverage scene through tastings at nearby wineries and breweries, perfect for adult enthusiasts.
  • Outdoor Recreation in Windsor Meadows: Embark on outdoor activities such as kayaking, fishing, or hiking in the lush surroundings that make this destination ideal for nature lovers.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of dining options in the area to experience authentic regional flavors that complement your stay in Windsor.
  • Visit Scenic Spots: Make time to discover the picturesque landscapes and peaceful spots nearby, perfect for relaxing or capturing memorable photos.
  • Plan Outdoor Activities: Engage in outdoor pursuits such as hiking or boating to enjoy the natural beauty that defines this destination.
  • Prepare for Your Trip: Research the local amenities and convenience stores around your vacation rentals to ensure a smooth and enjoyable visit.

Transportation Options

  • Windsor Transportation Services: Reliable local transportation options are available to help you explore the area with ease during your stay.
  • Public Transit: Bus services provide convenient access to nearby towns and attractions, making it simple to navigate here without a car.
  • Taxi and Rideshare: Taxis and rideshare apps offer flexible transportation choices for quick trips or airport transfers within the region.
  • Car Rentals: Renting a vehicle is an excellent way to discover hidden gems in the surrounding countryside at your own pace.

Local Customs Options

  • Respect for Local Traditions: When visiting here, embrace the community’s historical customs and show appreciation for local ways of life to enrich your experience.
  • Community Events Participation: Engaging in regional gatherings and festivals offers you a genuine connection with residents and an authentic taste of local culture.
  • Environmental Respect: Maintain the area's natural beauty by adhering to conservation practices and respecting outdoor spaces during your stay.
  • Historical Preservation: Appreciate and honor the region’s heritage by observing any local guidelines aimed at preserving historical sites and traditions.

Frequently Asked Questions About Windsor?

1. What are the top vacation rentals in Windsor?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 54 in the Windsor 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 Windsor. 

4. What is the cancellation policy for vacation rentals in Windsor, Maine?

Cancellation policies vary depending on the owner or property listing. It is recommended to review the specific cancellation terms listed with your selected property or contact the host directly for detailed information.

5. How do I confirm a reservation at a vacation rental in Windsor, Maine?

Once you complete the booking process and receive a confirmation email, your reservation is secured. Be sure to check any additional instructions provided by the owner to ensure a smooth check-in experience.

6. Are pets allowed in vacation rentals here, and what are the rules?

Pet policies differ between properties. You should verify individual rental details or contact the owner beforehand to confirm if pets are permitted and to understand any associated requirements or restrictions.

7. What amenities are typically included in Windsor, Maine vacation rentals?

Amenities vary by property, but common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Review each listing carefully to ensure it meets your needs, or reach out to the host for specific questions.

8. Is there a minimum stay requirement for booking vacation rentals in this region?

Minimum stay policies depend on the property and season. Check the specific listing for any minimum night requirements or contact the owner directly if you need more flexibility.