Wineglass vacation rentals

We found 11 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

Find out more about Wineglass

Why visit Wineglass

  1. Stunning scenery: Experience breathtaking views of Wineglass Mountain and the surrounding landscape.
  2. Outdoor activities: Engage in hiking and exploring the natural beauty of the national state park.
  3. Family-friendly atmosphere: Enjoy a range of attractions that cater to visitors of all ages.
  4. Historical experiences: Delve into local history at the nearby museum.
  5. Comfortable accommodations: Choose from charming vacation homes, cozy cabins, and modern condos for a perfect stay.

Popular types of accommodation around Wineglass

Planning a getaway to Wineglass? The adventure begins with selecting the perfect accommodation! Discover a range of popular options, from charming houses and cozy cabins to modern condos. Whether you're searching for Wineglass homes, the inviting Wineglass Inn, or a tranquil Wineglass mountain retreat, we’ve got you covered. Explore Wineglass vacation rentals that offer comfort and reassurance for an unforgettable stay.

  • Houses: The top choice among visitors to Wineglass, offering spacious and comfortable stays for families, friends, or couples.
  • Cabins: A close second, these rustic retreats immerse you in nature, perfect for those seeking adventure and tranquility.
  • Condos: Third on the list, condos provide a modern living experience with convenience and amenities.
  • Apartments: Ideal for longer stays, apartments offer a homely feel in a vibrant community.
  • Cottages: Rounding out the list, charming cottages offer a quaint and cozy atmosphere for a romantic getaway.**

Top attractions around Wineglass

Wineglass, Montana, is perfect for outdoor and adventure enthusiasts, offering stunning scenery and a variety of attractions. Explore the nearby river, delve into local history at the museum, or enjoy the beauty of the national state park. These points of interest provide a fantastic family experience and cater to those seeking adventure. Don't forget to consider hiking options to fully appreciate the area's natural beauty during your visit.

  1. Livingston Depot Center: A charming history museum showcasing the rich cultural heritage of Livingston. Explore fascinating exhibits that highlight the region’s railway history and local stories, all within a beautifully restored depot building.
  2. Sacajawea Park: A picturesque national park perfect for outdoor adventures. Enjoy scenic trails, picnic spots, and stunning views of the Yellowstone River, making it an ideal place for hiking, birdwatching, and relaxation.
  3. DePuy Spring Creek: A serene river known for its breathtaking scenery and excellent fishing opportunities. Experience the tranquility of nature while enjoying outdoor activities like fly fishing and leisurely walks along the water.

Things to do recommended for couples

For a romantic getaway in Wineglass, enjoy a round of golf at the luxurious Livingston Golf & Country Club, only 6.4km away. Embrace adventure at the nearby Crosscut Mountain Sports Center and Bridger Bowl Ski Area, both 30.6km away, perfect for skiing enthusiasts.

Things to do recommended for families

Families visiting Wineglass can enjoy a relaxing day at Lindley Park, located 32.2km away. This recreational area offers wellness vibes and plenty of space for kids to play and explore, making it a perfect spot for family bonding and outdoor fun.

Things to do recommended for groups

Groups visiting Wineglass can enjoy a round of golf at the Livingston Golf and Country Club, hike the scenic Tripple Tree Trailhead, or experience the vibrant atmosphere at Magic Diamond Casino, all within a short drive from your accommodation.

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

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's important to prioritise your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wineglass with a group: Think about how many bedrooms you require, as well as additional features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Wineglass with young kids: Travelling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to 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 trip wouldn’t feel complete without their furry companions. If you can relate to this, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wineglass: If you’re searching for vacation rentals that offer discounts for stays of a month or longer, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Wineglass

Wineglass, a charming neighborhood in Livingston, Montana, offers a perfect blend of outdoor adventure and breathtaking scenery. Explore the stunning views of Wineglass Mountain and enjoy leisurely drives along Wineglass Drive. With a family-friendly atmosphere, historical excursions, and opportunities for relaxation, Wineglass is an ideal getaway for those seeking both excitement and tranquility. Experience the allure of this captivating region and create unforgettable memories in the heart of Montana.

  • Paradise Valley: Nestled just 4.8km from Wineglass, Paradise Valley is renowned for its breathtaking natural landscapes and outdoor adventures. This enchanting valley offers a plethora of activities for nature enthusiasts, including hiking, fishing, and soaking in scenic views. Visitors can relax at local spas or unwind at luxury resorts that provide a tranquil escape. With its proximity to both a national state park and symbolic landmarks, Paradise Valley is an ideal destination for those seeking a serene yet adventurous getaway.
  • Historic Livingston: Located a mere 6.4km from Wineglass, Historic Livingston exudes charm and character, making it a delightful stop for anyone eager to explore the past. This quaint village is perfect for outdoor adventures, with access to recreational areas and spas offering rejuvenating body treatments. Just steps away, you can discover the fascinating visitor centre and experience the surrounding national parks. The blend of history and nature creates a unique atmosphere that invites you to explore and enjoy the best of both worlds.
  • Livingston: Also situated 6.4km from Wineglass, Livingston is a vibrant city steeped in history and culture. Known for its rich heritage, this city offers various excursions, including hiking and fishing opportunities that appeal to outdoor lovers. Stroll through charming shops or dine at local eateries to savour the region's flavours. With nearby natural parks and stunning landscapes, Livingston provides an inviting backdrop for a memorable vacation filled with exploration and relaxation.

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 month is July. Peak season runs from June to August, while off-peak times, like January, April and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January19.2°F (-7.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
February18.5°F (-7.5°C)No Rain (Dry)Mostly CloudyAverageAverage
March28.4°F (-2.0°C)No Rain (Dry)Mostly SunnyAverageAverage
April35.4°F (1.9°C)Light RainMostly SunnyLowSlightly Low
May46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyHighSlightly High
July65.8°F (18.8°C)No Rain (Dry)SunnyHighSlightly High
August64.4°F (18.0°C)No Rain (Dry)SunnyHighAverage
September55.6°F (13.1°C)Light RainSunnyAverageAverage
October39.6°F (4.2°C)Light RainMostly SunnyAverageAverage
November26.4°F (-3.1°C)No Rain (Dry)Mostly SunnyLowSlightly Low
December17.8°F (-7.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for an extended stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient platform to plan new adventures, pick up right where you left off, and manage your travel arrangements. You can easily access properties you've saved or booked, now categorized into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Wineglass?
Based on our data, houses are considered the most popular vacation rental type in Wineglass. But as you might expect, everyone's idea of an epic trip isn't the same. Vrbo has vacation rentals in a variety of shapes and sizes, so you're sure to discover the perfect match.
How much does it cost to rent a vacation rental in Wineglass?
Length of stay, property type and season are some factors that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect escape. From homey country cottages to expansive villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Wineglass?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Enter your Wineglass travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the amenities and features you want in your rental.
Are there large group vacation rentals in Wineglass?
You can pick from four vacation homes in Wineglass that can accommodate 10 or more people. Whether you're planning a get-together with extended family or a special event like a birthday party, there's enough space to get your group together under one roof.
Are there vacation rentals with WiFi in Wineglass?
You can pick from two vacation rentals with WiFi in Wineglass. If you want to disconnect from the world during your escape, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Wineglass?
You'll have to check with the Wineglass vacation rental you'd like on Vrbo as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a vacation rental in Wineglass for?
How long you can book a vacation rental in Wineglass depends on the property. Just enter your desired dates to display a list of options offering extended stays. With tons of creature comforts such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to discover the perfect place to call your home away from home in Wineglass.

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