Discover Your Perfect Windsor Vacation Homes

Windsor Luxury Rentals

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

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 right time to visit here can enhance your experience, as each season offers distinct advantages for exploring the region and enjoying your stay in trusted vacation rentals.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, you can enjoy warm weather ideal for exploring the local area and engaging in outdoor activities. This is when demand for vacation rentals increases as visitors seek to experience the region at its liveliest.

Average Temperature Daytime: around 80°F to 85°F - Nighttime: around 60°F to 65°F
autumn
Fall (September to November)

Early fall offers pleasant temperatures and vibrant scenery, making it a popular time for visitors looking to experience the changing colors and outdoor events in this region.

Average Temperature Daytime: about 70°F to 75°F - Nighttime: around 45°F to 50°F

Off-Season Highlights

image
Winter (December to February)

In winter, the area experiences colder weather with fewer tourists, offering an opportunity for quieter stays and cozy indoor experiences at your chosen vacation rental.

Average Temperature Daytime: around 20°F to 30°F - Nighttime: near 0°F to 10°F
image
Spring (March to May)

Spring brings milder temperatures and blooming landscapes, but the shoulder season sees less tourist activity, providing more affordable rates and a relaxed atmosphere for your visit.

Average Temperature Daytime: about 50°F to 60°F - Nighttime: around 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 areas perfect for family barbecues in this destination’s scenic surroundings.
  • Take advantage of spacious yards or gardens where you can relax or let the kids play freely.
  • Make the most of nearby lakes or rivers with access to kayaking, canoeing, or fishing activities.
  • Relax on private patios or decks that provide a peaceful setting to unwind after exploring the area.
  • Look for properties with outdoor fire pits for cozy evenings under the stars.
  • Benefit from well-maintained walking trails or biking paths that showcase the region’s natural beauty.
  • Experience the convenience of outdoor parking facilities designed to meet your travel needs in the area.

Top Attractions Around Windsor

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities and local attractions nearby, offering plenty of opportunities to explore and enjoy the natural beauty and culture of this welcoming destination.

image
image

Family Activities

  • Windsor Family Park: Enjoy a day outdoors at this local park, where you can have picnics, play on the playgrounds, and take relaxing walks along scenic trails.
  • Windsor Community Center: Participate in family-friendly activities, including sports, arts and crafts, and special events that foster community connection in the area.
  • Local Nature Trails: Explore nearby nature trails perfect for hiking and wildlife viewing, offering an educational experience for children and adults alike.
  • Family-Friendly Events: Attend seasonal festivals and community celebrations held throughout the year, providing fun-filled entertainment for all ages here in Windsor.
image

Adult Activities

  • Windsor Golf Course: Enjoy a day on the links at this well-maintained golf course, perfect for both beginners and seasoned players seeking a relaxing round in the area.
  • Local Wineries and Breweries: Explore the region's thriving wine and craft beer scene by visiting charming local wineries and breweries that offer tastings and tours.
  • Parks and Nature Trails: Discover scenic outdoor adventures along picturesque parks and nature trails that showcase the area's natural beauty and provide excellent opportunities for hiking and picnicking.
  • Shopping and Dining: Indulge in local shopping and dining experiences that highlight regional cuisine and unique shops, all within easy reach of your vacation rental here.

Other Places to Stay in Windsor, MN

Lake Traverse
Lake Traverse Vacation Rentals
More Places to Stay Near Windsor

Windsor 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 hidden gems and popular spots to immerse yourself in the local culture.
  • Plan Your Activities Ahead: Book outdoor adventures or guided tours in advance to ensure you maximize your time here without last-minute stress.
  • Choose a Prime Location: Opt for vacation rentals that are centrally located or close to key points of interest to easily access everything this destination has to offer.
  • Embrace the Local Cuisine: Take the opportunity to try regional dishes at nearby restaurants or markets, enriching your experience here in the region.

Transportation Options

  • Windsor Transit Services: Local bus services provide convenient transportation options within the region, making it easy to explore this destination without a car.
  • Rental Cars: Numerous rental agencies available in the area offer flexible vehicle options that cater to your travel needs during your stay here.
  • Taxi and Rideshare Services: Taxis and rideshare companies operate throughout the destination, offering reliable and quick transportation for short trips or airport transfers.
  • Airport Transportation: Nearby airports connect you to Windsor with various shuttle and charter service options for seamless arrivals and departures.

Local Customs Options

  • Local Festivals: Participating in community festivals offers a glimpse into the area's rich cultural traditions and lively spirit.
  • Traditional Cuisine: Sampling local dishes at neighborhood eateries can deepen your appreciation for regional culinary customs.
  • Craftsmanship and Artisanship: Visiting local markets and craft stores showcases the region's unique handmade goods and artistic heritage.
  • Festive Parades: Attending seasonal parades is a cherished tradition that highlights the area's community pride and celebratory atmosphere.

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 75 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, Minnesota?

Cancellation policies vary by property in this destination. You should review the specific listing details or contact the property owner directly to understand the cancellation terms and any applicable fees.

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

Additional fees such as cleaning fees, security deposits, or service charges are typically detailed in the listing. It’s best to read the full description or reach out to the host for clarification before completing your booking.

6. How do I know if a vacation rental in this area is suitable for my needs?

You can verify suitability by reviewing the property amenities, the number of bedrooms and bathrooms, and guest reviews on the listing page. Contact the host directly if you have specific requirements or questions.

7. What is the check-in and check-out process for these properties?

Check-in and check-out procedures are outlined in each listing. Many properties offer flexible options, but it’s advisable to confirm the details directly with the host prior to arrival.

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

Minimum stay requirements can vary depending on the property and season. Please refer to the individual listing or contact the owner to confirm any minimum night policies.