Windsor County Rentals by Owner
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- Air Conditioner
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- Pet Friendly
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- TV
- Security/Safety
Apartment
- Air Conditioner
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- TV
House
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- Accessibility
- Security/Safety
Cabin
- Parking
- Pet Friendly
- Balcony/Terrace
House
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your Windsor County vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windsor County
When should you plan your Rentals by Owner stay?
Timing your visit to this destination can enhance your experience, so consider the seasonal patterns and local climate to choose the perfect time for your vacation in Windsor County, Vermont, USA, when booking a rental by owner through Rent By Owner.
Peak Season Highlights
Summer (June to August)
During the summer months, this area experiences warm and inviting weather, making it an ideal time for outdoor activities and exploring scenic landscapes. Booking your rental here now ensures you enjoy the peak of the region's natural beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to October)
The vibrant fall foliage draws visitors from around the country, offering picturesque views and a festive atmosphere. Securing your rental by owner during this season allows you to fully immerse in the region’s colorful backdrop.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Spring (April to May)
In the spring, the area begins to bloom, providing a quieter experience before the busy summer season. Renting during this period offers a peaceful escape while enjoying mild temperatures.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F
Winter (December to February)
With cooler temperatures, winter transforms the region into a serene retreat with opportunities for cozy stays and scenic snowy views. Booking your vacation rental here early in the season can provide a quiet, off-the-beaten-path experience.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
Weekly Weather Forecast for Windsor County
How to Book Your Windsor County 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 County
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 access to spacious outdoor decks or patios perfect for relaxing and entertaining.
- Take advantage of lush gardens or landscaped yards that enhance your outdoor experience.
- Make the most of private or community swimming pools to cool off during warmer months.
- Benefit from well-maintained outdoor grills or BBQ areas for al fresco dining.
- Explore nearby trails or walking paths directly from your rental, ideal for outdoor enthusiasts.
- Use outdoor fire pits or fireplaces for cozy evenings under the stars.
- Relax in scenic outdoor seating areas that offer peaceful views of the surrounding countryside.
Top Attractions Around Windsor County
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities and cultural experiences just moments from your rental, making it an ideal destination for exploring the natural beauty and local attractions nearby.
Family Activities
- Vermont Institute of Natural Science (VINS): Engage your family with interactive exhibits and wildlife encounters at this renowned center dedicated to conservation education in the region.
- Okemo Mountain Resort: Enjoy year-round outdoor adventures such as skiing, snowboarding, or scenic gondola rides suitable for all ages here in Windsor County.
- Farms and Orchard Tours: Discover local farm life through guided tours and seasonal fruit picking experiences that provide a taste of the area's agricultural charm.
- Historic Downtown Windsor: Stroll through charming streets filled with shops, galleries, and family-friendly eateries that showcase the region’s rich history and culture.
Adult Activities
- Wine Tasting Tours: Explore local vineyards and enjoy guided tastings that showcase the region’s renowned wine production.
- Historical Museum Visits: Immerse yourself in the area's rich history by visiting local museums that tell the story of this destination's past.
- Golfing Experiences: Play a round at nearby golf courses designed to provide both relaxing and challenging options for enthusiasts.
Other Places to Stay in Windsor County, VT
Windsor County 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 visit with local festivals or seasonal activities that showcase the region's unique charm.
- Explore Nearby Nature: Take advantage of the region’s scenic landscapes by scheduling outdoor adventures like hiking or biking in nearby parks and trails.
- Choose Strategic Accommodation: Select a rental by owner that offers easy access to key attractions and amenities, ensuring a more convenient and enjoyable stay in this area.
- Engage with the Community: Participate in local markets, workshops, or cultural experiences to immerse yourself fully in the regional atmosphere and traditions.
Transportation Options
- Windsor County Regional Airport: This local airport offers convenient air travel options for visitors looking to arrive close to their rental accommodations in the area.
- Amtrak Rail Services: The rail system provides an eco-friendly and scenic transportation choice for exploring Windsor County and reaching nearby towns comfortably.
- Local Bus Services: Public bus routes connect key towns within the region, making it easy for you to navigate without a car during your stay.
- Car Rentals: Numerous rental agencies operate here, giving you the flexibility to explore scenic spots around Windsor County at your own pace.
Local Customs Options
- Respect for Local Artisans and Craftsmanship: You’ll notice a deep appreciation for handmade goods and artisans’ work that celebrate the region’s Vermont heritage.
- Farm-to-Table Culinary Traditions: Dining here often involves locally sourced ingredients, reflecting the area's commitment to sustainable and fresh food experiences.
- Preservation of Historical Sites and Customs: Respect for historic buildings and longstanding traditions is evident in the community’s efforts to maintain its rich history.
- Emphasis on Community Festivals and Events: Participating in local celebrations helps you connect with residents and enjoy the authentic regional culture during your stay.
Frequently Asked Questions About Windsor County Rentals by Owner
1. What are the top vacation rentals in Windsor County?
There are a lot of options in Windsor County. If you plan on staying in the Windsor County 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 County:
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Vermont Winter Getaway
- Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
- 11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
- Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
- Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
2. How many Rentbyowner vacation rentals are available in Windsor County?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1353 in the Windsor County 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 County.
3. What is the cancellation policy for a rental by owner in Windsor County, Vermont?
You should review the specific cancellation policy listed on the rental's page or contact the owner directly. Policies can vary between properties, so it's important to confirm the details before booking.
4. How do I confirm my reservation in Windsor County, Vermont?
Once you complete your booking through Rent By Owner, you'll receive a confirmation email with all the necessary details. For additional assistance, reach out to the property owner directly via the contact information provided.
5. Are there any specific check-in and check-out times for rentals in this region?
Check-in and check-out times are specified on each listing. If you have particular scheduling needs, contact the owner beforehand to discuss possible arrangements or exceptions.
6. What amenities are typically included in rentals by owner here?
Amenities vary depending on the property, but common features often include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Confirm the exact amenities with the owner during the booking process or by reviewing the listing details.
7. Is it safe to book a rental directly from an owner in this area?
Rent By Owner ensures all listings are verified for safety and reliability. However, it's advisable to read reviews, communicate clearly with the owner, and review the listing details carefully before finalizing your reservation.
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