Wineglass Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Wineglass
Price found within the past 48 hours. Click for updated prices.
320 Guest Ranch
CA $1,536
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bozeman (BZN)
9.4/10 Exceptional! (1,007 reviews)
Beautiful location close to the Gallatin River. Cabins are comfortable and amenities are good, as are available activities. About an hour from West Yellowstone park entrance and from Bozeman. Restaurant was very good, including the substantial breakfast included. Murphy on the front desk was a delight and made us feel very welcome.
Reviewed on Sep 1, 2026
RSVP Hotel
Midtown
CA $1,565
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bozeman (BZN)
9.6/10 Exceptional! (1,036 reviews)
Very nice place to stay. Unique for sure but pretty much what we expected and hoped for. Location is great and staff was very helpful.
Reviewed on Sep 2, 2026
Wineglass Hotel Deals
The Skyhawk Lodge - Wonderful home with incredible views on 10 acres!
Livingston MT
10/10 Exceptional! (8 reviews)
"Absolutely stunning view. Clean, bright and peaceful. Loved our stay here."
Reviewed on Dec 16, 2025
Jackalope Lodge · Spacious Lodge Home with Breathtaking Mtn Views
Livingston MT
9.8/10 Exceptional! (20 reviews)
"This is a great place to stay. The views are phenomenal. We really enjoyed sitting on the back porch with a glass of wine watching the sunset each night."
Reviewed on Jul 27, 2026
Econo Lodge Livingston Gateway to Yellowstone
111 Rogers Ln Livingston MT
Fully refundable
CA $115
CA $132 total
Oct 1 - Oct 2
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Room was very clean. The furniture and decor was dated and the bed frame/support made a loud sound when accidentally kicked. Breakfast included nice assortment of food and drinks."
Reviewed on Sep 2, 2026
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 $1,536, 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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.