Windsor Cottage Rentals
House
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- Accessibility
- Security/Safety
Cabin
- Parking
- Pet Friendly
- Balcony/Terrace
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Parking
- TV
House
- Security/Safety
- Child Friendly
- Internet
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Why Choose Rent By Owner for your Windsor Cottage Rentals?
What makes our Cottage Rentals 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
When should you plan your Cottage Rentals stay?
Timing your visit to Windsor, Vermont ensures you experience the region's natural beauty and tranquil surroundings at their best, making it the ideal season to book a cozy cottage here through RentByOwner.com for a memorable and seamless vacation experience.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this area experiences lively outdoor activities and vibrant local events, making it an ideal time for outdoor enthusiasts to visit. Expect longer daylight hours that enhance your sightseeing and relaxation.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to October)
Autumn brings stunning foliage and pleasant weather, perfect for exploring scenic views and enjoying the region’s natural beauty at its peak. This season is popular for those seeking picturesque scenery and outdoor adventures.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
The winter months offer a quieter escape with fewer visitors, providing a tranquil setting for cozy stays in cottages. While it can be chilly, this is a great time for quiet reflection and enjoying the serene snow-covered landscape.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
Spring (March to May)
Late winter and early spring feature milder weather and blooming flora, making it a peaceful time to explore the region without the crowds. The fresh air and awakening nature create a charming ambiance for your visit.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Windsor
How to Book Your Windsor Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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 spacious outdoor patios or decks perfect for relaxing and entertaining outdoors.
- Many rentals feature private gardens or yards where you can unwind amidst natural surroundings.
- Expect accessible fire pits for cozy evenings under the stars with family or friends.
- Look for properties that offer outdoor dining areas to savor meals amid scenic views.
- Some cottages include outdoor recreational equipment like bikes or kayaks for adventures nearby.
- Enjoy well-maintained walking trails or paths directly from your rental to explore the area’s natural beauty.
- Many outdoor amenities are designed to enhance your experience in this picturesque region, making your stay more memorable.
Top Attractions Around Windsor
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities such as hiking, biking, and exploring scenic parks, making it an ideal destination to experience the natural beauty and tranquility that surrounds your stay in Windsor, Vermont.
Family Activities
- Windsor County Museum Dive into the area's rich history with engaging exhibits that teach both children and adults about the region's past.
- Local Parks and Outdoor Play Areas Enjoy quality family time exploring scenic parks featuring walking trails, picnic spots, and playgrounds perfect for outdoor adventures.
- The Green Mountain Nature Trail Discover the natural beauty of the region on accessible trails designed for families to hike and observe local wildlife.
- Family-Friendly Events and Festivals Experience seasonal festivities and community events that create lasting memories for families visiting here.
Adult Activities
- Windsor County Fairgrounds Experience local culture and entertainment at this vibrant venue, perfect for engaging with the community during your stay.
- The Vermont Farm & Table Tour Discover farm-to-table dining experiences that highlight the region's fresh produce and culinary traditions.
- Windsor State Park Enjoy lakeside relaxation, scenic picnics, and outdoor activities amid the natural beauty of this popular park.
- Vermont Institute of Natural Science (VINS) Explore nature and wildlife exhibits that offer educational insights into the area's rich biodiversity.
Other Places to Stay in Windsor, VT
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region’s natural beauty by discovering scenic trails and waterways to make your stay memorable.
- Visit nearby cultural sites: Immerse yourself in the area's rich history and vibrant arts scene to gain a deeper appreciation of this destination.
- Plan for seasonal events: Check the calendar for festivals or markets that showcase the region’s unique traditions and enhance your experience.
- Choose a well-located cottage: Select accommodations that offer easy access to key attractions and amenities, ensuring a convenient and enjoyable visit.
Transportation Options
- Windsor Station: This station offers convenient train services connecting you to major cities and nearby regions, making travel flexible and straightforward.
- Local Bus Services: Regular bus routes operate throughout the area, providing an affordable and reliable way to explore Windsor and its surroundings.
- Car Rentals: Several rental agencies are available locally, giving you the freedom to navigate this destination at your own pace and visit more secluded spots.
- Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber or Lyft are accessible here, offering quick and comfortable transportation right from your cottage stay.
Local Customs Options
- Respect for Local Crafts and Artisans: Here, it’s customary to appreciate the region’s handcrafted goods, which reflect the area's rich cultural heritage.
- Community Gatherings and Town Meetings: Participating in or observing local town meetings is a valued tradition that fosters community involvement.
- Celebration of Seasonal Festivals: The area hosts seasonal festivals that celebrate local history and produce, offering an authentic experience for visitors.
- Environmental Respect and Conservation: Visitors are encouraged to honor local natural resources by practicing responsible outdoor activities and conservation efforts.
Frequently Asked Questions About Windsor Rental Cottages
1. What are the top Cottages 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 Cottages in Windsor:
- Meadow View- 35 Acres outside your door
- Sunset Cabin - your private romantic hideaway
- Long Range Mountain Views in West Windsor
- Snapdragon Inn
- Antique farmhouse with spectacular mountain view in a bucolic setting.
- Luxury Vermont Vacation Rental Private Hot Tub!
- Exquisite Log Home with views near Woodstock, Vermont
- Luxury Vermont Vacation Rental: Private Hot Tub!
- Totally Restored Grand Mansion & Estate overlooking the CT River
- Kennedy’s House
2. How many Cottages are available in Windsor?
Currently, the total number of properties listed by RBO in 2026 is over 1 in the Windsor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windsor.
3. What is the cancellation policy for cottages in Windsor, Vermont?
Cancellation policies vary depending on the listing. You should review the specific cancellation terms outlined on the property’s page or contact the owner directly to understand any fees or deadlines involved.
4. Are there specific check-in and check-out times for cottages in this area?
Check-in and check-out times are typically specified in each listing. For precise details, please refer to the individual cottage’s information or contact the owner to confirm your arrival and departure times.
5. How do I find out about additional charges or fees when booking a cottage here?
Additional fees such as cleaning, security deposits, or extra guest charges are usually disclosed in the listing details. To ensure clarity, review the property description thoroughly or reach out directly to the host.
6. Is it possible to bring pets to cottages in this region, and are there any restrictions?
Pet policies differ from one cottage to another. You should check the listing to see if pets are allowed or contact the owner to discuss any restrictions or requirements regarding furry friends.
7. What amenities are generally included with cottages in Windsor, Vermont?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, heating, and parking. Confirm the available features of your chosen cottage by reviewing its listing or contacting the owner directly.
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