Discover Your Perfect Windsor Vacation Homes

Why Choose Rent By Owner for your Windsor 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 Windsor

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit ensures you enjoy the best climate and local events, making your experience in Windsor, New York, memorable and tailored to your preferences when booking your vacation rentals here.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, this destination experiences its peak tourist season, making it ideal for those seeking lively outdoor activities and vibrant local events. Expect higher occupancy rates in vacation rentals, so early booking is recommended.

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

The autumn months bring colorful foliage and pleasant weather, attracting visitors looking for scenic beauty and outdoor exploration. This is a popular time to enjoy the region’s natural charm, so securing your stay well in advance is advisable.

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

Off-Season Highlights

image
Winter (December to February)

Cold winter temperatures typically lead to fewer visitors, providing a quieter experience. It’s an excellent period for travelers interested in cozy stays and exploring the area at a relaxed pace, often with lower rental rates.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 15°F to 25°F
image
Spring (March to May)

Early spring sees fewer tourists as the region transitions from winter to warmer weather. This off-peak period offers a peaceful ambiance and more availability in vacation rentals, perfect for those seeking tranquility.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°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 grilling facilities for delicious meals in the fresh air.
  • Relax in a spacious backyard or garden area perfect for outdoor activities.
  • Make use of private patios or decks to unwind while taking in scenic views of the region.
  • Take advantage of convenient parking options for easy access to your rental in this destination.
  • Explore nearby walking trails or paths that allow you to experience the natural beauty of the area.
  • Utilize community or shared outdoor spaces that encourage social gatherings and relaxation.
  • Benefit from outdoor fire pits for cozy evenings under the stars with family and friends.

Top Attractions Around Windsor

What attractions are nearby?

While staying here, you can enjoy a variety of outdoor activities, cultural experiences, and local attractions that showcase the best of Windsor, New York, USA.

image
image

Family Activities

  • Windsor Historical Museum: Dive into the area's rich history with engaging exhibits and local stories that are perfect for family outings.
  • Windsor Town Park: Enjoy outdoor activities, picnics, and playground fun in this scenic park ideal for family relaxation and recreation.
  • Windsor Greenways Trails: Explore family-friendly hiking and biking trails that offer scenic views and active adventures amidst the natural beauty of here.
  • Local Farms and Pick-Your-Own Spots: Experience hands-on farm experiences and seasonal fruit picking, making it a memorable day trip for families visiting the area.
image

Adult Activities

  • Windsor Wine Tasting Tour: Enjoy sampling local wines at nearby vineyards, offering a refined experience amidst the region’s scenic landscapes.
  • Historical Museum Exploration: Discover the area's rich heritage and culture through engaging exhibits housed in local museums.
  • Nature Trails and Hiking: Explore picturesque trails designed for hikers of all levels, providing serene views and outdoor recreation opportunities.
  • Local Dining Experiences: Indulge in regional cuisine at acclaimed restaurants that showcase the region’s culinary delights.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar before your trip to align your stay with festivals or seasonal activities that highlight the region's unique culture.
  • Discover Nearby Dining Options: Explore local eateries around your vacation rental to enjoy authentic regional cuisine and support small businesses.
  • Make Use of Outdoor Space: Take advantage of outdoor areas at your accommodation or explore nearby parks to experience the natural beauty here fully.
  • Engage with the Community: Participate in community-led tours or markets to gain deeper insights into the area's history and traditions during your visit.

Transportation Options

  • Windsor Transit Services: Local public transportation options provide convenient access to exploring the area and nearby attractions.
  • Private Car Rentals: Renting a car offers the flexibility to discover the region at your own pace, especially for traveling between nearby towns and outdoor sites.
  • Taxi and Rideshare Services: Reliable taxis and rideshare options make quick trips within Windsor and to surrounding areas straightforward and hassle-free.
  • Regional Bus Lines: Connecting services are available for longer journeys across the region, providing an affordable way to reach neighboring destinations from here.

Local Customs Options

  • Lumberjack Traditions: Embrace the region’s logging heritage through local events and community gatherings that celebrate this vital industry.
  • Farmers’ Markets: Visiting the area’s farmers’ markets is a great way to experience local produce, crafts, and the friendly atmosphere that defines here.
  • Seasonal Festivals: Participating in seasonal festivals allows you to enjoy the vibrant customs that highlight this destination’s cultural calendar.
  • Historical Celebrations: The region’s historical commemorations offer insights into its past and are an integral part of the local community's 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 62 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, New York?

Cancellation policies vary depending on the property listing. To ensure your plans are flexible enough, review the specific cancellation terms provided in the listing details or contact the property owner directly before booking.

5. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning fees, service charges, or deposits may apply and are detailed within each listing. Make sure to read the full reservation description or reach out to the host for clarification.

6. How do I ensure my booking is secure when reserving a vacation rental in this area?

Book through a trusted platform that offers secure payment options and verified listings. Always verify the property's reviews and communicate with the owner through official channels to confirm your reservation.

7. What amenities can I expect from vacation rentals in Windsor, New York?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, parking, and heating or air conditioning. For specific amenities, refer to the individual listing details or contact the host directly.

8. What is the check-in and check-out process for rentals here?

Check-in and check-out procedures are outlined in each listing. Many properties offer self-check-in options for convenience, but it’s best to confirm these details with the owner prior to your arrival to ensure a smooth stay.