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Discover Your Perfect Windsor Rentals by Owner

Windsor Rentals by Owner

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10.0 (1 Review)
House
Afton Cabin
  • Air Conditioner
  • Parking
  • View
View Availability
More Top-Rated Rentals by Owner in Windsor Area

Why Choose Rent By Owner for your Windsor vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Choosing the ideal time to visit here can enhance your experience, as seasonal variations in this destination influence the available activities and overall ambiance for your stay.

Peak Season Highlights

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Summer (June to August)

During the summer months, the region experiences peak visitor traffic as travelers seek warm weather and outdoor activities.

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

Autumn draws visitors with its vibrant foliage and pleasant temperatures, making this a popular time for exploring the outdoors and cultural events.

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

Off-Season Highlights

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Winter (December to February)

The winter months see fewer travelers, offering a quieter escape with cooler temperatures perfect for cozy getaways.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Early spring features milder weather and less crowding, ideal for those seeking tranquility and natural beauty.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windsor

How to Book Your Windsor vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Windsor Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 grilling with a private barbecue area to prepare meals amidst scenic surroundings.
  • Relax on spacious patios or decks that offer picturesque views of the region's natural beauty.
  • Take advantage of outdoor dining spaces perfect for enjoying meals al fresco in this destination.
  • Make use of a well-maintained backyard or garden area for lounging, playing, or outdoor activities.
  • Benefit from access to nearby walking or hiking trails directly from your rental property.
  • Experience the convenience of outdoor fire pits for cozy evenings under the stars.
  • Utilize outdoor sports equipment such as bikes, kayaks, or fishing gear often available at properties here.

Top Attractions Around Windsor

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and local attractions that showcase the region’s natural beauty and cultural heritage, making your stay in Windsor an enriching experience.

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Family Activities

  • Windsor Nature Trail: You can enjoy a family-friendly hike along this scenic trail, offering opportunities to observe local wildlife and appreciate the region's natural beauty.
  • Downtown Windsor Park: Visiting this park provides a perfect setting for picnics, playground fun, and relaxing afternoons with your loved ones in the heart of the area.
  • Local Farm Visits: Experience the charm of working farms around here, where you and your family can learn about sustainable agriculture and even pick fresh produce.
  • Historic Windsor Museum: Explore the area's rich heritage with educational exhibits and interactive displays that entertain and inform visitors of all ages.
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Adult Activities

  • Wine Tasting Experiences: Discover local wineries in the area that offer guided tastings, perfect for an adult day out exploring regional flavors.
  • Fine Dining and Culinary Tours: Indulge in the region's best restaurants and culinary tours that showcase the area's unique gastronomy.
  • Historic Sightseeing: Explore historical landmarks and sites around this destination to gain insight into its rich cultural heritage.
  • Outdoor Recreation: Enjoy outdoor activities such as hiking or fishing in nearby parks and natural reserves for a relaxing escape.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Familiarize yourself with upcoming events in the region to enhance your experience and make the most of your time here.
  • Choose a Rental Close to Attractions: Opt for a rental by owner that’s conveniently located near key sites and amenities, ensuring easier access to everything the area has to offer.
  • Explore Seasonal Activities: Take advantage of the local climate and seasonal activities to enjoy an authentic experience during your stay.
  • Connect with Local Hosts: Engage with your rental host for insider tips and personalized recommendations to enrich your visit here.

Transportation Options

  • Windsor Bus Service: This reliable bus service connects you to neighboring towns and regional hubs, making it easy to explore the surrounding area from your rental.
  • Local Taxi Services: Convenient taxi options are available for quick transportation around Windsor and to nearby attractions within the region.
  • Car Rentals: Renting a vehicle offers flexibility and comfort if you prefer exploring the broader area at your own pace during your stay.
  • Regional Rail Connections: Accessible rail services provide a scenic and efficient way to travel between Windsor and major cities in New York State.

Local Customs Options

  • Respect for Community Events: Participating in local gatherings and respecting community traditions helps you connect authentically with the area's residents.
  • Local Dining Etiquette: When dining at eateries or hosting guests, observing the region’s customs around food sharing and tipping enhances your experience here.
  • Celebration of Regional Holidays: Attending or acknowledging local holidays, which often involve specific customs, allows you to immerse yourself in the area's cultural heritage.
  • Environmental Preservation Practices: Engaging in eco-friendly habits such as recycling and conservation reflects the area's commitment to maintaining its natural beauty for visitors and locals alike.

Frequently Asked Questions About Windsor Rentals by Owner

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. How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 43 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. 

3. What is the cancellation policy for rental properties by owner in Windsor, New York?

Cancellation policies vary by individual listing. You should review the specific terms on the property’s page or contact the owner directly to understand the cancellation details before booking.

4. How do I communicate with the property owner in Windsor, NY, before booking?

You can use the booking platform’s messaging feature to ask questions or clarify details with the owner. It's recommended to communicate well in advance to ensure all your questions are answered.

5. Are there any additional fees when booking a rental by owner in this area?

Additional fees such as cleaning, service charges, or security deposits may apply and are detailed on the listing. Review the total cost carefully before confirming your reservation.

6. What amenities are typically included in owner-managed rentals in Windsor, New York?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. Check each listing for a detailed list of included amenities to ensure it meets your needs.

7. How do I know if a rental property by owner in the region is suitable for my stay?

Review the property descriptions, photos, and guest reviews carefully. If you have specific requirements, contact the owner directly to confirm availability and suitability before booking.

More Rentals You May Like Near Windsor

More Top-Rated Rentals by Owner in Windsor Area