Discover Your Perfect Wineglass Vacation Homes

Wineglass Luxury Rentals

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Wineglass Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Wineglass 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 Wineglass

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can greatly enhance your experience, allowing you to enjoy the region's natural beauty and outdoor activities at their peak during the most suitable seasons.

Peak Season Highlights

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Summer (June to August)

During the summer months, you'll enjoy warm days ideal for exploring the scenic outdoors of Livingston. The region's vibrant atmosphere makes it a perfect time to book your vacation rental and experience local activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 45°F to 55°F
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Fall (September to October)

Early fall offers stunning fall foliage and mild weather, making it a popular season for travelers seeking picturesque scenery. Securing your vacation rental now ensures you can fully enjoy this colorful time here.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 35°F to 45°F

Off-Season Highlights

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Winter (November to February)

In winter, the region transforms into a peaceful retreat with colder temperatures perfect for cozying up in your vacation rental. Visiting during this time often means fewer crowds and more exclusive experiences.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 10°F to 20°F
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Spring (March to May)

Spring brings milder weather and budding landscapes, providing a quiet period before the summer rush. Booking your accommodation here now allows for relaxed exploration of the area’s natural beauty.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Wineglass

How to Book Your Wineglass 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 Wineglass

More Top-Rated Vacation Rentals in Wineglass 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

  • Enjoy spacious outdoor areas perfect for relaxing and taking in the scenic views of the region.
  • Take advantage of private patios or decks to dine al fresco amidst the natural surroundings.
  • Make use of outdoor grilling facilities to prepare delicious meals during your stay.
  • Benefit from access to well-maintained gardens or landscaped yards that enhance your outdoor experience.
  • Explore nearby hiking trails and outdoor pathways directly accessible from your rental property.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Relish the convenience of parking areas designed for outdoor storage of gear or recreational equipment.

Top Attractions Around Wineglass

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic nature trails in the surrounding region, providing endless opportunities for adventure just moments from your vacation rental.

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Family Activities

  • Livingston River Adventures: Embark on a family-friendly float trip along the Yellowstone River, where you can enjoy the scenic beauty and observe local wildlife in their natural habitat.
  • Livingston Depot Center Tour: Discover the history of the area with a guided tour of this historic train depot, offering an engaging experience for kids and adults alike.
  • Local Wildlife Viewing: Explore nearby nature preserves and parks to spot native animals and learn about the region’s diverse ecosystems during your stay.
  • Fishing in Livingston: Try fishing at popular spots along the river, providing a relaxing outdoor activity that families can enjoy together while soaking in the natural surroundings.
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Adult Activities

  • Wineglass Winery Tour: Experience a guided tour of the local winery to savor regional wines and learn about the area's viticulture heritage.
  • Fly Fishing on the Yellowstone River: Enjoy a relaxing day casting your line along the renowned Yellowstone River, known for its excellent fly fishing opportunities.
  • Hiking in the Livingston Area: Explore scenic trails that wind through the region's breathtaking landscapes, perfect for outdoor enthusiasts seeking adventure.
  • Wildlife Viewing Tours: Embark on a guided tour to observe Montana’s diverse wildlife within natural habitats, providing memorable experiences for nature lovers.

Wineglass Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region's scenic trails and outdoor adventures to truly experience the natural beauty surrounding your vacation rental.
  • Connect with the community: Engage with the friendly locals and discover authentic regional cuisine and cultural experiences during your stay here.
  • Plan ahead for seasonal events: Check the area's event calendar to participate in seasonal festivals or markets that highlight the region’s unique traditions.
  • Prioritize comfort and convenience: Choose a well-reviewed vacation rental that offers amenities suited to your needs, ensuring a relaxed and enjoyable visit in this destination.

Transportation Options

  • Livingston Municipal Airport: You can opt for a quick and convenient regional flight through this nearby airport, ideal for reaching the area's scenic destinations efficiently.
  • Rental Car Services: Local rental car agencies provide flexible transportation options, allowing you to explore the region at your own pace from here.
  • Public Transit:** Buses and shuttles operate within the town and connect to key attractions, offering an affordable way to navigate the area without a personal vehicle.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are readily available, providing reliable transportation to and from your vacation rentals in Livingston's tranquil surroundings.

Local Customs Options

  • Western Hospitality: Locals in the area pride themselves on their friendly and welcoming attitude, making your stay in Livingston feel like visiting a close-knit community.
  • Montana Ranch Traditions: Embrace the region’s ranching heritage by respecting local customs such as livestock safety and participating in community events when possible.
  • Outdoor Etiquette: When exploring the scenic landscapes, it’s customary to follow Leave No Trace principles to preserve the natural beauty of this destination.
  • Local Art and Craftsmanship: Appreciating regional art and handmade crafts is a valued tradition that enriches your experience here and supports local artisans.

Frequently Asked Questions About Wineglass?

1. What are the top vacation rentals in Wineglass?

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

2. Which vacation homes in Wineglass are best for families?

If you are looking for a family-friendly vacation home in Wineglass, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wineglass:

3. How many Rentbyowner vacation rentals are available in Wineglass?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 93 in the Wineglass 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 Wineglass. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it’s best to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

5. Are there any specific amenities included with my booking here?

Amenities differ depending on the property, so be sure to check the individual listing for details on features such as Wi-Fi, kitchen facilities, or outdoor spaces.

6. How do I find the most accurate availability and rates for a stay?

Availability and pricing are updated regularly on the listing page. It’s recommended to book early and reach out to the property owner if you have questions about rates or availability.

7. Is there a minimum stay requirement for booking here?

Minimum stay requirements can vary between properties. Please review each listing’s policies or contact the owner to confirm the length of your stay.

8. What should I do if I need assistance during my stay?

Support options are usually provided in the listing details or through direct communication with the owner. You can also consult the contact information provided on the booking platform for prompt assistance.