Discover Your Perfect Windsor Vacation Homes

Windsor Luxury Rentals

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Find More Windsor Villas, Resorts, & Rentals on BedroomVillas

Windsor Pet Friendly Vacation Rentals

7.5 (205 Reviews)
Hotel
Westbridge Inn & Suites
  • Air Conditioner
  • Parking
  • Pet Friendly
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8.0 (736 Reviews)
Hotel
Best Western State Fair Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (2 Reviews)
Apartment
Unit A Country house near Warrensburg
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
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5.5 (192 Reviews)
Hotel
Super 7 Motel
  • Air Conditioner
  • Parking
  • Pet Friendly
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See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io

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 optimal time to visit here ensures you enjoy the region's unique atmosphere and make the most of your stay in this welcoming destination.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During these months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the surrounding area's natural beauty and outdoor activities.

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

This period offers pleasant temperatures and less humidity, perfect for sightseeing and experiencing the region's vibrant local events.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Mid Winter (December to February)

The colder months bring quieter attractions and fewer crowds, providing a peaceful retreat in this destination’s scenic surroundings.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Late Fall (November)

As the leaf colors fade, the region experiences a slowdown, offering a calm and relaxed atmosphere for your stay in here’s charming environment.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°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

  • You can enjoy outdoor dining areas perfect for a relaxing meal in the fresh air.
  • Many properties feature spacious yards suitable for family games and outdoor activities.
  • Expect to find access to private or shared outdoor pools for cooling off during warm days.
  • Some rentals include patios or decks where you can unwind while taking in scenic views of the region.
  • Enjoy the convenience of outdoor grills for preparing delicious meals during your stay.
  • Several properties offer fire pits, ideal for cozy evenings under the stars.
  • You might also find well-maintained gardens that add to the natural charm of your stay here.

Top Attractions Around Windsor

What attractions are nearby?

While staying in Windsor, Missouri, you can explore nearby outdoor activities, charming local parks, and recreational spots that allow you to enjoy the natural beauty and relaxed atmosphere of this region.

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Family Activities

  • The Windsor Heritage Museum: Dive into the area's rich history through engaging exhibits and local stories that will entertain the whole family.
  • Winery Tours and Tastings: Explore family-friendly wineries in the region where you can enjoy scenic views and learn about local viticulture practices.
  • Outdoor Recreation at Lake Windsor: Spend a day kayaking, fishing, or picnicking by the tranquil waters of Lake Windsor, perfect for outdoor family fun.
  • Community Events and Festivals: Join seasonal celebrations and local festivals that showcase the region's culture and provide entertainment for all ages.
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Adult Activities

  • Windsor Golf Course: Enjoy a relaxing day on the lush fairways and scenic views at this local golf course, perfect for enthusiasts seeking a leisurely challenge.
  • Lake Viking Recreation Area: Explore outdoor activities such as fishing, boating, and picnicking beside the tranquil waters of Lake Viking, just a short drive from here.
  • Historic Downtown Windsor: Stroll through charming streets filled with antique shops, local eateries, and cultural spots that showcase the area's rich history.
  • Wine Tasting Tours: Discover regional wineries offering wine tasting experiences where you can sample local flavors amid picturesque vineyard settings.

Other Places to Stay in Windsor, MO

Royal Oaks Hospital
Royal Oaks Hospital Vacation Rentals
More Places to Stay Near Windsor

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or happenings, enhancing your experience in Windsor, Missouri.
  • Explore Nearby Outdoor Spaces: Take advantage of the region’s scenic parks and trails by planning outdoor activities during your visit to this destination.
  • Choose Comfortable Accommodations: Select well-reviewed vacation rentals that provide the amenities you need for a relaxing and enjoyable stay here.
  • Discover Local Dining Options: Sample regional cuisine by exploring dining spots nearby, enriching your experience within the area’s culinary scene.

Transportation Options

  • Windsor Transit System: This local bus service offers convenient transportation within the area, making it easy to explore nearby attractions and amenities.
  • Rental Cars: Several car rental agencies are available here, providing flexible options for exploring the region at your own pace.
  • Taxi Services: Reliable taxi companies operate in this destination, offering quick and straightforward transportation for short trips or airport transfers.
  • Bike Rentals: For an eco-friendly and leisurely way to discover the surroundings, bike rentals are readily available here, allowing you to enjoy the scenery firsthand.

Local Customs Options

  • Local Food Traditions: You will notice a strong emphasis on hearty, home-cooked meals that reflect the region’s agricultural roots here in Windsor.
  • Community Celebrations: Participating in local festivals and parades offers an authentic glimpse into the traditions cherished by residents of this area.
  • Historic Preservation: Respect for the region’s history is evident in the well-maintained architecture and preservation efforts visible throughout Windsor.
  • Local Craftsmanship: Support for indigenous artisans and craftspeople is prominent, with handmade goods often showcased at markets and events around town.

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. How many vacation rentals have private pools in Windsor?

There are 1 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 98 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. 

5. What is the cancellation policy for vacation rentals in Windsor, Missouri?

The cancellation policy varies by listing. To ensure you understand the specific terms, please review the cancellation details provided on the property page or contact the property owner directly before booking.

6. Are there any house rules or restrictions I should be aware of when booking a vacation rental in Windsor?

Yes, each property has its own set of house rules and restrictions, which are detailed on the listing. Be sure to read these carefully or reach out to the host if you have questions.

7. How do I find vacation rentals with flexible booking options in this destination?

You can filter your search to include properties that offer flexible cancellation policies or instant booking features, making it easier to plan your stay with confidence.

8. What amenities are typically available in Windsor area vacation rentals?

Most rentals in the region offer essential amenities such as Wi-Fi, fully equipped kitchens, and private parking. Specific amenities are listed on each property page, so review those details during your search.

9. How do I contact the property owner if I have special requests or questions about my stay?

You can message the property owner directly through the booking platform. Many hosts are responsive and happy to assist with special requests or additional information about their vacation rentals.