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  3. Windsor
  4. Cabin Rentals

Windsor Cabin Rentals

8.4 (13 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
New
Cabin
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
New
Cabin
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Why Choose Rent By Owner for your Windsor Cabin Rentals?

What makes our Cabin 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 Cabin Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when this area experiences milder weather and fewer crowds, allowing you to enjoy the tranquility and natural beauty while booking your ideal cabins for a relaxing getaway.

Peak Season Highlights

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Spring (March to May)

During the spring months, the area sees an influx of visitors seeking pleasant weather and blooming landscapes, making it an ideal time for enjoying the natural beauty around your Windsor cabin.

Average Temperature Daytime: 60°F to 75°F - Nighttime: 45°F to 55°F
summer
Summer (June to August)

Summer is a popular season when warm temperatures attract travelers who want to relax and explore, offering longer daylight hours perfect for outdoor activities near your Windsor cabin.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 65°F to 70°F

Off-Season Highlights

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Fall (September to November)

In the fall, the region experiences cooler weather and fewer visitors, providing a tranquil environment for those seeking a peaceful retreat at their Windsor cabin.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
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Winter (December to February)

Winter offers a quiet escape with colder temperatures and sparse crowds, ideal for cozy stays at your Windsor cabin amid serene winter scenery.

Average Temperature Daytime: 30°F to 45°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Windsor

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.

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 seating areas perfect for relaxing and dining while taking in the scenic views of the region.
  • Take advantage of private patios or decks that offer a great spot for morning coffee or evening gatherings.
  • Relax by a cozy outdoor fire pit, ideal for unwinding under the stars after exploring the area.
  • Benefit from well-maintained yards or gardens that create a peaceful environment amidst the natural surroundings.
  • Make use of outdoor grills to prepare delicious meals during your stay in this inviting destination.
  • Utilize nearby hiking trails or nature walks conveniently accessible from your accommodation.
  • Experience the beauty of the region through outdoor recreational equipment like kayaks or paddleboards if available onsite.
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Family Activities

  • Windsor Park Enjoy a family picnic and outdoor playtime amid scenic landscapes and well-maintained facilities that cater to children and adults alike.
  • Missouri River Access Spend a day fishing, kayaking, or simply relaxing by the water at this popular spot perfect for outdoor adventures in the area.
  • Windsor Community Center Engage in family-friendly events, recreational activities, or explore local classes designed for all age groups.
  • Local Nature Trails Discover scenic walking and biking trails that wind through the region, offering a great way for families to connect with nature and enjoy fresh air.
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Adult Activities

  • Windsor Vineyards Tour Experience local wine at a renowned vineyard, offering tastings and scenic views that make for a relaxing adult activity in the area.
  • Golfing at Windsor Golf Course Enjoy a day on the greens at this popular golf course, perfect for those seeking leisure and outdoor recreation close to your accommodations.
  • Explore Local Craft Breweries Discover the region’s craft beer scene by visiting several nearby breweries, where you can sample unique brews and enjoy a lively social atmosphere.
  • Visit Historic Downtown Windsor Take a leisurely stroll through downtown, exploring charming shops, cafes, and local landmarks that showcase the area's rich heritage.

Other Places to Stay in Windsor, MO

Royal Oaks Hospital

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Early: Arriving early ensures you have ample time to settle into your Windsor, Missouri accommodation and make the most of your stay.
  • Explore Local Nature: Take advantage of nearby outdoor activities to fully experience the scenic beauty that this region offers.
  • Discover Hidden Gems: Ask locals or your host about lesser-known spots to visit, providing authentic experiences during your visit.
  • Pack Thoughtfully: Bring essentials tailored to Windsor, Missouri, including weather-appropriate clothing and outdoor gear for a comfortable stay.

Transportation Options

  • Personal Vehicles Navigating the area by car offers flexibility and convenience for exploring Windsor and its surrounding regions.
  • Rental Cars Rent a vehicle locally to easily access your chosen cabin and nearby attractions in this tranquil destination.
  • Public Transit Buses provide an economical way to get around, connecting you to key points within the region without hassle.
  • Taxi and Rideshare Services Available options like taxis or ridesharing apps ensure quick, reliable transportation during your stay here.

Local Customs Options

  • Traditional Amish Practices: In this area, you'll notice a strong presence of Amish customs, which influence local crafts and community events.
  • Farmers Markets: Visiting the weekly farmers markets offers insight into locally grown produce and handmade goods that reflect regional traditions.
  • Community Festivals: Annual festivals celebrate regional heritage with music, food, and parades that highlight the area's cultural roots.
  • Respect for Nature: The region emphasizes conservation and outdoor respect, making it customary to engage in eco-friendly practices during your stay.

Frequently Asked Questions About Windsor Rental Cabins

1. How many Cabins are available in Windsor?

Currently, the total number of properties listed by RBO in 2026 is over 15 in the Windsor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cabins in Windsor. 

2. What is the cancellation policy for cabins in this area?

Cancellation policies vary depending on the listing, so you should review the specific terms outlined for each property before booking. If you have questions about cancellations or need to make changes, contacting the property owner directly is recommended.

3. Are there flexible booking options available for a stay in Windsor?

Many cabins offer flexible booking options, but availability and terms differ by property. It's best to check the specific property's details and contact the host if you require special arrangements or extended stays.

4. What amenities are typically included in cabins here?

Cabins in this destination generally come equipped with essential amenities such as Wi-Fi, kitchen facilities, heating or air conditioning, and outdoor spaces. To confirm specific features, reviewing individual listings or communicating with the owner is advised.

5. How do I know if the cabin is suitable for my needs?

Listings include detailed descriptions, photos, and guest reviews to help you determine suitability. For particular requirements or questions about accessibility or facilities, reaching out directly to the owner ensures you find the perfect fit.

6. Is there a minimum stay requirement for booking cabins in this region?

Minimum stay policies can vary among properties, especially during peak seasons or holidays. It’s important to check the specific listing for any minimum night requirements or contact the owner for clarification.