A snow-covered mountain range with a dense forest in the foreground.

Wineglass Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Wineglass Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 28 - Jan 2

    Extended Stay America Premier Suites - Belgrade - Bozeman - Yellowstone Airport + Flight

    Belgrade
    5 nights
    2.5 star property
    9.2/10 - Wonderful (682 reviews)
    "Always clean and the staff is great!"
    Reviewed October 31, 2026
    Roundtrip • Detroit (DTW) - Bozeman (BZN)
    DTW - BZN • 1 stop BZN - DTW • 2 stops
    CA $1,888
    CA $1,772
    per traveller
    found 8 hours ago
    Extended Stay America Premier Suites - Belgrade - Bozeman - Yellowstone Airport
  • Dec 28 - Jan 2

    Aspects Big Sky + Flight

    Gallatin Gateway
    5 nights
    4.0 star property
    10/10 - Exceptional (18 reviews)
    "Beautiful place to stay at. Well equipped with everything you would need. Perfect for families with little kids"
    Reviewed May 31, 2026
    Roundtrip • Detroit (DTW) - Bozeman (BZN)
    DTW - BZN • 1 stop BZN - DTW • 2 stops
    CA $7,092
    CA $6,291
    per traveller
    found 8 hours ago
    Aspects Big Sky
  • Dec 28 - Jan 2

    RSVP Hotel + Flight

    Midtown
    5 nights
    3.5 star property
    9.6/10 - Exceptional (1,051 reviews)
    Roundtrip • Detroit (DTW) - Bozeman (BZN)
    DTW - BZN • 1 stop BZN - DTW • 2 stops
    CA $2,001
    CA $1,819
    per traveller
    found 8 hours ago
    RSVP Hotel
  • Dec 28 - Jan 2

    Field & Stream Lodge Bozeman + Flight

    Bozeman
    5 nights
    4.0 star property
    9.2/10 - Wonderful (857 reviews)
    Roundtrip • Detroit (DTW) - Bozeman (BZN)
    DTW - BZN • 1 stop BZN - DTW • 2 stops
    CA $1,951
    CA $1,782
    per traveller
    found 8 hours ago
    Field & Stream Lodge Bozeman
  • Dec 28 - Jan 2

    The LARK Bozeman + Flight

    Downtown Bozeman
    5 nights
    3.0 star property
    9.2/10 - Wonderful (1,006 reviews)
    "Amazing location & they even do smores every night!"
    Reviewed November 8, 2026
    Roundtrip • Detroit (DTW) - Bozeman (BZN)
    DTW - BZN • 1 stop BZN - DTW • 2 stops
    CA $2,124
    CA $1,976
    per traveller
    found 8 hours ago
    The LARK Bozeman

Where to stay in Wineglass

Find the best Wineglass areas and neighborhoods for the activities you enjoy most.

Historic Livingston

Unique features of Historic Livingston include the historic sites and restaurants. Make a stop by Yellowstone Gateway Museum or Yellowstone River while you're exploring the area.

Wineglass Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Wineglass vacation package cost?

The most affordable Wineglass package is CA $1,772, so your dream escape can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to tailor make a package that matches your travel style.

How do I get a cheap travel package to Wineglass?

Our Wineglass vacation packages promise plenty of savings for the savvy traveler. For the best deal, simply bundle your flights, hotels and extras (including tours) into a convenient package. But bargain prices are only the start of your next epic adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 properties globally to pick from. No matter your budget or style, there's a vacation package here just for you.

How far in advance should I book my Wineglass vacation?

While not all air carriers advertise tickets early, you can normally start comparing international flights on Expedia up to a year in advance. This is the time when you can nab some incredible deals. If you're purchasing tickets last minute, you may still be in luck. Discounted prices occasionally become available just weeks prior to departure.

What does an Expedia Wineglass travel package include?

Travel packages include rental cars, flights and hotels, but you can mix and match them to create your dream Wineglass trip. You can also add on experiences and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find anywhere else.

What should I know before booking a Wineglass travel package?

Locking in all the parts of your escape together is a terrific way to save. Combine your car rentals, flights and hotels into a handy little package. But it's not just hotels. Expedia has all types of properties, including vacation rentals like mountain cabins and serviced residences. You've got choices galore!

Can I choose my airline with a Wineglass Expedia vacation package?

You can, and with over 550 airlines to pick from across the globe, you have loads of choice. Browse the available options and see which airline suits your budget and needs.

If I'm not able to travel, can I cancel my Wineglass vacation package?

Yes, you can. We realize even the best-laid plans can go awry, so we're happy to help if you need to make changes to your Wineglass vacation package. You may be able to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.