Wineglass Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Holiday Package Deals in Wineglass

Price found within the past 48 hours. Click for updated prices.
The Roosevelt Hotel - Yellowstone

The Roosevelt Hotel - Yellowstone

2.5 out of 5
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bozeman (BZN)
9.2/10 Wonderful! (1,014 reviews)
A good hotel to stay

Reviewed on Aug. 2, 2025

Yellowstone Riverside Cottages

Yellowstone Riverside Cottages

2.5 out of 5
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bozeman (BZN)
9.6/10 Exceptional! (803 reviews)
Awesome place! Highly recommend! Wish we could have stayed longer

Reviewed on Aug. 2, 2025

The Ridgeline Hotel at Yellowstone, Ascend Hotel Collection

The Ridgeline Hotel at Yellowstone, Ascend Hotel Collection

3 out of 5
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bozeman (BZN)
8.8/10 Excellent! (1,111 reviews)
Clean and friendly. Rooms were quiet. Only stayed one night so didn't explore the hotel or area much.

Reviewed on Aug. 2, 2025

Antler Lodge - Gardiner MT

Antler Lodge - Gardiner MT

3 out of 5
per person
Oct 10 - Oct 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bozeman (BZN)
8.6/10 Excellent! (1,000 reviews)
The Antler restaurant at the property was excellent! Bison cheesesteak sandwich and Elk Meatloaf sandwich are fantastic!

Reviewed on Jul. 31, 2025

Wineglass Hotel Deals

Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
1515 W Park St, Livingston, MT
Fully refundable
The price is CA $97 per night from Sep 2 to Sep 3
CA $97
CA $107 total
Sep 2 - Sep 3
includes taxes & fees
5.4/10 (681 reviews)
"Always enjoy staying here."

Reviewed on Jul. 30, 2025

Comfort Inn & Suites
Econo Lodge Livingston Gateway to Yellowstone

Econo Lodge Livingston Gateway to Yellowstone

3 out of 5
111 Rogers Ln, Livingston, MT
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Aug 24 to Aug 25
CA $153
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Friendly front staff and excellent hot breakfast."

Reviewed on Jul. 30, 2025

Econo Lodge Livingston Gateway to Yellowstone
Yellowstone River Inn & Suites

Yellowstone River Inn & Suites

2.5 out of 5
114 Loves Ln, Livingston, MT
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Aug 4 to Aug 5
CA $170
CA $198 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Very pleasant stay."

Reviewed on Aug. 1, 2025

Yellowstone River Inn & Suites
See all 519 properties in Wineglass
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.
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Frequently asked questions

How much does a Wineglass vacation package cost?
The most affordable Wineglass package is CA $1,374, 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.

Discover the most popular places to visit in Wineglass

Livingston Depot Center

You can study the exhibits at Livingston Depot Center, a museum with a storied past, during your trip to Historic Livingston. While in this walkable area, you can savor the restaurants and breweries.

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