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Discover Your Perfect Wineglass Rentals by Owner

Wineglass Rentals by Owner

9.8 (43 Reviews)
Apartment
Charming private studio
  • Parking
  • Balcony/Terrace
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Wineglass Area

Why Choose Rent By Owner for your Wineglass 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 Wineglass

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as understanding seasonal patterns in this destination helps you find the perfect rental by owner through Rent By Owner for a memorable stay in Livingston's scenic region.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy ideal weather for outdoor activities and scenic views in this area, making it a popular time to visit for those seeking an active vacation.

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

This season offers vibrant foliage and cooler temperatures, attracting visitors who want to experience the region's natural beauty at its peak while enjoying more tranquil surroundings.

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)

The winter months bring colder weather and quieter landscapes, making it an ideal time if you're looking for peaceful accommodations and a cozy retreat here.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
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Spring (March to May)

As the region transitions into warmer weather, this is a great period to find less crowded rental options while witnessing the early signs of seasonal renewal.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 25°F to 35°F

Weekly Weather Forecast for Wineglass

How to Book Your Wineglass 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 Wineglass

More Top-Rated Rentals by Owner in Wineglass 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 spacious outdoor patios or decks with scenic views of the surrounding landscape.
  • Take advantage of outdoor grilling areas for preparing meals amidst nature.
  • Access well-maintained hiking trails directly from your rental to explore the area's natural beauty.
  • Relax in private yards or gardens that provide a peaceful retreat after a day of adventures.
  • Utilize outdoor fire pits perfect for evening gatherings under the stars.
  • Benefit from ample parking spaces for outdoor recreation equipment like boats or ATVs.
  • Make use of outdoor recreational amenities such as picnic tables and shaded sitting areas for outdoor dining.

Top Attractions Around Wineglass

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities in the area, from scenic hikes to fishing opportunities, all conveniently accessible when you choose a rental by owner in this destination.

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Family Activities

  • Livingston Historic Downtown Tour: Explore the charming streets and learn about local history, providing an engaging experience for the whole family.
  • Yellowstone River Activities: Enjoy fishing, kayaking, or a simple riverside picnic along the scenic Yellowstone River that flows through the area.
  • Local Nature Trails: Discover the region's outdoor beauty by hiking or biking on family-friendly trails that showcase Montana’s stunning landscapes.
  • Wildlife Viewing in the Region: Observe native animals in their natural habitat, making it a memorable adventure for nature-loving families visiting here.
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Adult Activities

  • Wine Tasting Tours: Discover local wineries and enjoy guided tastings that highlight the region’s renowned wine craftsmanship.
  • Fly Fishing in Livingston: Experience the thrill of fly fishing in nearby rivers, where you'll find abundant trout and scenic surroundings.
  • Hiking Adventures: Explore diverse trails offering breathtaking views of the surrounding mountains and natural beauty of this area.
  • Wildlife Viewing: Observe native wildlife in their natural habitat at nearby parks and open spaces, perfect for outdoor enthusiasts seeking a peaceful escape.

Wineglass Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Tours: Take advantage of nearby scenic areas and outdoor activities to fully immerse yourself in the region's natural beauty.
  • Plan Ahead for Dining Options: Research local dining establishments or grocery stores in advance to enjoy authentic regional flavors during your stay.
  • Connect with Your Host: Communicate with your rental owner to get personalized tips and ensure a smooth experience throughout your visit.
  • Utilize Nearby Recreation Facilities: Make the most of available recreational amenities to enhance your relaxation and enjoyment here.

Transportation Options

  • Personal Vehicle: Renting your own car offers the most flexibility for exploring the scenic surroundings and accessing remote areas near Livingston.
  • Local Taxis: Taxi services are available in the region, providing convenient transportation options without the need for personal driving.
  • Public Transit: Bus routes connect this part of Montana to nearby towns and attractions, making it a reliable choice for short trips around the area.
  • Shuttle Services: Shuttle operators serve the region, offering scheduled rides to key locations such as airports and popular destinations within Livingston and beyond.

Local Customs Options

  • Western Hospitality Customs: You will notice a warm greeting and friendly interactions, reflecting the region’s welcoming spirit that characterizes this part of Montana.
  • Respect for Nature: It’s customary here to show appreciation for the natural surroundings, whether through responsible outdoor activities or conservation-minded behavior.
  • Local Craftsmanship: Supporting handmade local crafts and products is appreciated, embodying the area’s pride in its artisanal traditions and heritage.
  • Community Events: Participating in or observing community gatherings and celebrations emphasizes the region’s close-knit culture and shared history.

Frequently Asked Questions About Wineglass Rentals by Owner

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. How many Rentbyowner vacation rentals are available in Wineglass?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 55 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. 

3. How do I find the cancellation policy for a rental by owner in Wineglass, Livingston?

The cancellation policy is detailed within each listing, so it’s important to review the specific terms provided by the property owner before confirming your booking. If you have further questions, contacting the owner directly can provide clarity.

4. What amenities are typically included in rentals by owner in Livingston's area?

Amenities vary by property, but many rentals offer essential features such as Wi-Fi, parking, and kitchen facilities. To ensure the rental meets your needs, check the listing details or reach out to the owner for specific amenities offered.

5. Is there a minimum stay requirement for rentals by owner here?

Minimum stay requirements depend on the individual property and are specified in each listing. Reviewing the listing details will help determine if the rental aligns with your travel plans, or you can contact the owner directly for clarification.

6. How do I handle payments and security deposits when booking a rental by owner?

Payments and security deposits are managed through the booking platform, with details outlined in each listing. Always review the payment terms and contact the owner if you need additional information or clarification about security deposits.

7. What steps should I take if I encounter issues during my stay in a rental by owner?

If any issues arise during your stay, contact the property owner promptly using the contact details provided in the listing. For unresolved problems, the booking platform offers support to ensure your experience in this region remains positive.

More Rentals You May Like Near Wineglass

More Top-Rated Rentals by Owner in Wineglass Area