Wineglass vacation rentals

We found 12 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Wineglass that are perfect for your trip. Vacation homes provide the best amenities for your family, friends, or furry companion, like cable TV and a washer and dryer. At the end of the day, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.

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Find out more about Wineglass

Why visit Wineglass

  • Outdoor Adventures: Wineglass offers stunning landscapes and activities like hiking, fishing, and exploring national parks.
  • Rich Cultural Experience: Discover local history through museums and scenic river tours that highlight the region's heritage.
  • Family-Friendly Activities: Wineglass is perfect for family excursions, providing a variety of fun experiences for all ages.
  • Diverse Accommodations: Choose from private vacation homes, cozy cabins, or modern condos for a perfect stay.
  • Relaxing Retreat: Enjoy the tranquil atmosphere surrounded by rolling hills and expansive outdoor spaces.

Popular types of accommodation around Wineglass

You’ve chosen Wineglass for your next getaway, and now it’s time to find the perfect place to stay. This charming destination offers a variety of popular accommodations, including Houses, cozy Cabins, and modern Condos. Whether you’re looking for a scenic retreat at Wineglass Ranch or planning a fun-filled stay at nearby ranch campgrounds and campsites, you’ll discover the ideal spot to unwind and make lasting memories.

  • Houses: These are the top choice for visitors looking for spacious and comfortable accommodations, perfect for families or groups.
  • Cabins: A cozy option that offers a rustic experience amidst nature, ideal for those seeking a peaceful retreat.
  • Condos: These modern units provide convenient amenities and are often located in vibrant areas.
  • Apartments: A practical choice for travelers wanting a home-like setting with easy access to local attractions.
  • Cottages: Charming and quaint, these rentals offer a delightful getaway experience with a personal touch.**

Top attractions near Wineglass

Wineglass, Montana is perfect for outdoor enthusiasts seeking adventure and breathtaking scenery. Explore local attractions such as history museums, scenic rivers, and national state parks that offer a rich cultural experience. Whether you're traveling solo, with family, or friends, Wineglass has something for everyone to enjoy amidst its natural beauty.

  • Livingston Depot Center: This historical museum, located 4 miles from Wineglass, offers a glimpse into the rich cultural heritage of Livingston. The beautifully restored depot features exhibits that highlight the town's railroad history and vibrant local stories, providing a fascinating experience for history enthusiasts.
  • Sacajawea Park: Just 3 miles away, this national park is perfect for outdoor adventurers. With stunning scenery, hiking trails, and picnic areas, visitors can immerse themselves in nature while enjoying breathtaking views of the surrounding landscape.
  • DePuy Spring Creek: Situated 4 miles from Wineglass, this picturesque river is an ideal spot for those who love the outdoors. Its tranquil waters and scenic surroundings provide opportunities for fishing, picnicking, and enjoying nature’s beauty.

Things to do recommended for couples

For a romantic getaway near Wineglass, enjoy a round of golf at the luxurious Livingston Golf & Country Club, just 4 miles away. If you're seeking adventure, head to Bridger Bowl Ski Area or Crosscut Mountain Sports Center, both 19 miles away, for skiing and outdoor fun together.

Things to do recommended for families

Families visiting Wineglass can enjoy a relaxing day at Lindley Park, located 20 miles away. This recreational area offers wellness vibes and plenty of space for kids to play and explore, making it a perfect spot for a family outing.

Things to do recommended for groups

Enjoy a round of golf at the Livingston Golf and Country Club, explore the culture at the Shane Lalani Center for the Arts, or embark on an adventure at the Tripple Tree Trailhead for a scenic hike. These experiences promise fun and bonding for your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Wineglass

If you're planning a trip with a group, family, pets, or looking for extended stays, be sure to adjust your filters according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wineglass with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Wineglass with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wineglass: For many families, a vacation isn’t truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wineglass: Welcome. If you're searching for vacation rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay near Wineglass

Wineglass, nestled in the charming Livingston, Montana, offers an ideal blend of outdoor adventure and stunning scenery. Explore the breathtaking Montana landscape, featuring rolling hills and expansive outdoor spaces perfect for relaxation. Nearby cities and neighborhoods invite you to immerse yourself in the region's rich history and family-friendly excursions. Whether you seek luxury or a peaceful retreat, Wineglass is the perfect base for your unforgettable vacation experience.

  • Livingston: Nestled in the scenic foothills of the Absaroka Mountains, Livingston serves as a gateway to outdoor adventures. Known for its stunning landscapes, this vibrant city offers a plethora of recreational activities, making it a haven for nature enthusiasts. Popular spots include nearby state parks and resorts that provide opportunities for hiking, fishing, and wildlife watching. Travelers can enjoy the charm of local shops and restaurants while soaking in the breathtaking views of the surrounding mountains and rivers, ensuring an unforgettable experience.
  • Paradise Valley: Located a mere 3 miles from Wineglass, Paradise Valley is a picturesque valley renowned for its natural beauty and outdoor pursuits. This serene area is perfect for those seeking adventure, with options for hiking, horseback riding, and exploring the stunning landscape. Visitors can unwind at local spas or resorts after a day of exploration. The valley is also home to several national parks and state parks, offering ample opportunities to connect with nature and enjoy the tranquility of the Montana wilderness.
  • Historic Livingston: Just 4 miles from Wineglass, Historic Livingston is a charming village steeped in rich history and stunning scenery. This quaint area invites travelers to explore its historic buildings and vibrant arts scene. Outdoor enthusiasts will find plenty to do, with access to recreational areas and notable landmarks. The local visitor center provides insights into the area's heritage, while the nearby national parks offer breathtaking vistas and diverse wildlife, making Historic Livingston a must-visit for those looking to immerse themselves in the beauty and culture of Montana.

Best time to go to Wineglass

If you're planning a trip to Wineglass, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in June, June to July, July to August and August, while off-peak times, like January, January, April, April, November and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.2°F (-7.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
January19.2°F (-7.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
February18.5°F (-7.5°C)No Rain (Dry)Mostly CloudyAverageAverage
February18.5°F (-7.5°C)No Rain (Dry)Mostly CloudyAverageAverage
March28.4°F (-2.0°C)No Rain (Dry)Mostly SunnyAverageAverage
March28.4°F (-2.0°C)No Rain (Dry)Mostly SunnyAverageAverage
April35.4°F (1.9°C)Light RainMostly SunnyLowSlightly Low
April35.4°F (1.9°C)Light RainMostly SunnyLowSlightly Low
May46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
May46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyHighSlightly High
June56.5°F (13.6°C)Light RainMostly SunnyHighSlightly High
July65.8°F (18.8°C)No Rain (Dry)SunnyHighSlightly High
July65.8°F (18.8°C)No Rain (Dry)SunnyHighSlightly High
August64.4°F (18.0°C)No Rain (Dry)SunnyHighSlightly High
August64.4°F (18.0°C)No Rain (Dry)SunnyHighSlightly High
September55.6°F (13.1°C)Light RainSunnyAverageAverage
September55.6°F (13.1°C)Light RainSunnyAverageAverage
October39.6°F (4.2°C)Light RainMostly SunnyAverageAverage
October39.6°F (4.2°C)Light RainMostly SunnyAverageAverage
November26.4°F (-3.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
November26.4°F (-3.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
December17.8°F (-7.9°C)No Rain (Dry)Mostly SunnyAverageAverage
December17.8°F (-7.9°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save money on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Plan your next group trip by booking a qualifying Vrbo and earn valuable OneKeyCash on your reservation. As the planner, you truly benefit from this opportunity. When you become a member of our travel rewards program, One Key, you can immediately access exclusive savings and earn OneKeyCash on eligible bookings. Sign up today to start enjoying these fantastic savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy way to plan your travel. You can start new trips, continue from where you last left off, or organize all your travel plans in one place. Your saved or booked properties will be neatly arranged under categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Wineglass?
In Wineglass, vacation houses and cabins are the most popular types of rental accommodations, with several available throughout the area. These properties typically feature spacious interiors, multiple bedrooms, and outdoor spaces for relaxation or enjoying the scenic surroundings. Many of these rentals come with amenities such as fully equipped kitchens, cozy living areas, and sometimes even fireplaces, making them ideal for families or groups looking for a comfortable retreat in the beautiful Montana landscape.
Are there any beach house rentals in Wineglass?
In Wineglass, Montana, there are beach house rentals available, offering a great experience in this scenic area. These vacation homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and cozy living areas, great for families or groups looking to unwind in a tranquil setting. Many properties also include outdoor spaces, such as decks or patios, where guests can enjoy the beautiful natural surroundings.
How much does it cost to rent a vacation home in Wineglass?
Prices for vacation rentals in Wineglass vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wineglass to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wineglass vacation house rentals?
You can find great discounts on house rentals in Wineglass on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Wineglass?
In Wineglass, popular rental amenities include a deck or patio, which allows guests to enjoy the stunning Montana landscape. Travelers can expect fully equipped kitchens for preparing meals, complete with modern appliances like blenders for convenience. Many rentals also feature cozy fireplaces, great for warming up after a day of outdoor activities. Onsite parking is available, making it easy for guests to explore the surrounding areas without worry.
Can I find family house rentals in Wineglass?
In Wineglass, Montana, there are some family-friendly house rentals available. This picturesque area offers a tranquil setting, superb for families looking to enjoy outdoor activities. Many of these homes feature spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Visitors can appreciate the nearby natural beauty, with opportunities for hiking and sightseeing in the surrounding landscapes. The locale is known for its peaceful atmosphere, making it an excellent choice for families seeking a relaxing getaway.
Are there any Wineglass vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wineglass with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Wineglass?
A long-stay vacation rental in Wineglass is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Wineglass for a vacation rental?
The best time to visit Wineglass for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant summer period entices travelers seeking adventure, offering warm temperatures typically in the mid-70s to mid-80s Fahrenheit. Visitors can indulge in a variety of outdoor activities, including hiking, fishing, and exploring the picturesque landscapes that define this beautiful region.

During July, the atmosphere in Wineglass is lively, as both locals and tourists come together to enjoy the stunning natural surroundings. This is an ideal time for outdoor enthusiasts to explore the nearby trails and partake in water sports on local lakes, all while soaking up the sun in a comfortable and inviting climate.

For those looking for a more budget-friendly experience, consider planning your visit in November. While this month is part of the low season, it offers a peaceful retreat, great for enjoying the tranquility of the area. November is a great time to appreciate the stunning autumn colors and enjoy the serene beauty of Wineglass without the crowds.
Are there any remote work vacation rentals in Wineglass?
In Wineglass, Montana, there are several vacation rentals that cater to remote work needs. Many of these properties are equipped with reliable internet services and Wi-Fi in the rooms, ensuring that travelers can stay connected while enjoying their getaway. The accommodations often feature comfortable workspaces, allowing for a conducive environment to balance work and leisure.

The serene surroundings of Wineglass provide a great backdrop for remote work, offering a peaceful atmosphere that can enhance productivity. Additionally, travelers can take advantage of local outdoor activities during their downtime, such as hiking and exploring the picturesque landscapes that Montana is known for. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wineglass vacation rental?
Book your Wineglass vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wineglass, Montana, United States of America?
In Wineglass, Montana, visitors can enjoy a range of outdoor attractions that highlight the area's natural beauty. The nearby Flathead National Forest offers stunning landscapes for hiking, camping, and wildlife viewing, with trails suitable for all skill levels. The picturesque Flathead Lake, one of the largest natural lakes in the western United States, is great for boating, fishing, and swimming, providing a serene environment for relaxation.

Additionally, the scenic views of the surrounding mountains create a beautiful backdrop for photography and outdoor activities. Wineglass is also close to Glacier National Park, where travelers can explore breathtaking vistas, historic chalets, and diverse ecosystems. This proximity makes it a great base for those looking to experience the park's famous Going-to-the-Sun Road and its numerous hiking trails.
Can I change or cancel my Wineglass home rental booking on Vrbo?
To find Wineglass vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wineglass vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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