Discover Your Perfect Windham Vineyards and Winery Rentals by Owner

Windham Vineyards and Winery Rentals by Owner

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10.0 (1 Review)
Apartment
Windham Ridge Chalet
  • Air Conditioner
  • Parking
  • View
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More Top-Rated Rentals by Owner in Windham Vineyards and Winery Area

Why Choose Rent By Owner for your Windham Vineyards and Winery vacation rental?

What makes our Rentals by Owner 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 Windham Vineyards and Winery

When should you plan your Rentals by Owner stay?

Choosing the ideal time to visit ensures you experience the best of this destination’s scenic beauty and vibrant atmosphere, making your stay in Windham's wine country truly memorable.

Peak Season Highlights

autumn
Fall (September to November)

During this time, you can experience the region's stunning autumn foliage while enjoying warm days and cool evenings at Windham Vineyards and Winery.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
summer
Summer (June to August)

The summer months offer lively vineyard tours and outdoor activities with longer daylight hours and vibrant scenery here in the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Off-Season Highlights

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Late Winter (February to March)

Visit during the late winter to enjoy quieter surroundings and scenic winter views in this part of New York when tourism slows down.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

As the region transitions into spring, you’ll find fewer crowds, making it a peaceful time for your vineyard visit before the peak season begins.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windham Vineyards and Winery

How to Book Your Windham Vineyards and Winery 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 Windham Vineyards and Winery

More Top-Rated Rentals by Owner in Windham Vineyards and Winery Area

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 outdoor dining with private patios or decks to savor the scenic views.
  • Take advantage of well-maintained gardens or landscaped areas perfect for relaxing walks.
  • Benefit from access to outdoor seating areas designed for unwinding amidst nature.
  • Make use of designated barbecue or grilling stations to enhance your culinary experience outdoors.
  • Relax in outdoor lounging spaces that provide comfort and serenity in the region's fresh air.
  • Explore nearby walking trails or pathways accessible from your rental for outdoor adventures.
  • Utilize outdoor recreational amenities such as fire pits or picnic areas, ideal for gatherings in this destination.

Top Attractions Around Windham Vineyards and Winery

What attractions are nearby?

Enjoy a variety of outdoor activities nearby, including scenic hiking trails and nature explorations that showcase the beauty of the region surrounding Windham Vineyards and Winery in Windham.

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Family Activities

  • Guided Vineyard Tours: Discover the secrets of wine-making with family-friendly tours that explore the vineyards and introduce you to local winemaking traditions.
  • Wine Tasting Events for Families: Enjoy tasting sessions designed for all ages, offering a variety of non-alcoholic beverages alongside traditional wines to keep everyone engaged.
  • Picnic in the Vineyard: Relax and unwind with a scenic picnic among the vines, where you can indulge in local delicacies while soaking up the beautiful surroundings.
  • Seasonal Festivals and Family Days: Participate in community festivals held throughout the year that feature entertainment, activities, and local crafts suitable for children and adults alike.
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Adult Activities

  • Wine Tasting Tours: You can enjoy guided wine tasting experiences that showcase the region’s renowned vineyards and varietals, perfect for wine enthusiasts visiting this destination.
  • Take a leisurely stroll through picturesque vineyards, where you can appreciate the scenic beauty and learn about the winemaking process firsthand.
  • Indulge in culinary delights paired with local wines in on-site restaurants, offering a relaxed and flavorful way to spend your day here.
  • Participate in wine education sessions and tastings led by expert vintners, enriching your understanding of the region’s unique wine culture.

Windham Vineyards and Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Season: Scheduling your stay outside the busy weekends can help you enjoy a more relaxed experience and better access to the winery’s amenities.
  • Book Early Through Rent By Owner: Securing your rental in advance ensures you find the perfect accommodation close to the vineyard, especially during popular times of the year.
  • Explore Local Dining Options: Take advantage of the area's charming eateries to complement your wine tasting adventures and discover regional flavors.
  • Participate in Guided Tours or Tastings: Enhance your experience by joining scheduled winery tours or tastings available here, gaining insights into the winemaking process while enjoying exclusive samples.

Transportation Options

  • Rental Car Services: Local rental agencies in Windham offer convenient vehicle options, allowing you to explore the region at your own pace during your stay.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services like Uber operate in the area, providing reliable transportation for quick trips around Windham and nearby attractions.
  • Public Transit: Bus services connect Windham with surrounding towns, making it easy to access the region’s scenic spots without the need for a personal vehicle.
  • Private Shuttle Services: Several private shuttle providers offer tailored transportation solutions, ideal for group visits or winery tours in the area.

Local Customs Options

  • Respect for the Vineyard Traditions: Visitors often observe locally cherished customs regarding the handling and tasting of wines, which reflect the region's deep-rooted winemaking heritage.
  • Greeting Etiquette: When engaging with staff or neighbors, a warm and polite greeting is customary, showing appreciation for the welcoming nature of this area.
  • Environmental Awareness: The community values sustainable practices, so you may notice local efforts to preserve the natural beauty that makes this destination unique.
  • Celebration of Local Harvests: Participating in seasonal festivals and tastings allows you to appreciate the region’s rich agricultural traditions and community spirit.

Frequently Asked Questions About Windham Vineyards and Winery Rentals by Owner

1. What are the top vacation rentals in Windham Vineyards and Winery?

There are a lot of options in Windham Vineyards and Winery. If you plan on staying in the Windham Vineyards and Winery area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windham Vineyards and Winery:

2. How many Rentbyowner vacation rentals are available in Windham Vineyards and Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 109 in the Windham Vineyards and Winery 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 Windham Vineyards and Winery. 

3. What is the cancellation policy for rental properties booked through Rent By Owner in Windham Vineyards and Winery?

The cancellation policy varies depending on the individual owner’s terms listed on the rental property page. You should review the specific cancellation details before booking to understand any applicable fees or restrictions.

4. How do I contact the property owner if I have questions about my stay in this area?

You can reach out directly to the property owner through the messaging feature on Rent By Owner. Owners are typically responsive and happy to assist with any questions regarding your upcoming stay.

5. Are there any additional fees I should be aware of when booking a rental by owner in Windham?

Additional fees, such as cleaning fees or security deposits, are specified in the listing details. Be sure to review these charges prior to confirming your reservation to avoid surprises.

6. What amenities are typically available in rentals by owner in this destination?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, parking, and outdoor spaces. Detailed amenities are listed on each property page, so check those to ensure they meet your needs.

7. Is there a minimum stay requirement for rentals booked through Rent By Owner in Windham?

Minimum stay requirements differ depending on the property. These details are displayed on each listing, so please review them carefully before completing your booking.

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