Title: Wineglass Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,840 Expedia.ca

[Hotels in Wineglass](https://expedia.ca/Wineglass-Livingston-Hotels.0-n553248635976480080-0.Travel-Guide-Filter-Hotels)[Flights to Livingston](https://expedia.ca/Cheap-Flights-To-Livingston.d8604.Travel-Guide-Flights)[Things to do in Livingston](https://expedia.ca/Things-To-Do-In-Livingston.d8604.Travel-Guide-Activities)[Wineglass Car Rentals](https://expedia.ca/Car-Rentals-In-Wineglass.d553248635976480080.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Wineglass Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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

## Top Holiday Package Deals in Wineglass

Price found within the past 48 hours. Click for updated prices.

![320 Guest Ranch](https://images.trvl-media.com/lodging/3000000/2180000/2179400/2179303/31caf978_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 320 Guest Ranch

CA $1,840

per person

Jun 8 - Jun 14

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Bozeman (BZN)

9.4/10 Exceptional! (1,000 reviews)

Clean room, great staff, beautiful surroundings. Few things to note: 1) Hotel restaurant is open for breakfast only. Closest restaurant is 10+ minutes drive away 2). Very icy road surface on the property. Staff did their best and put down gravels in front of your cabin everyday but it remains sheet of ice most of the day. Be careful driving and walking

Reviewed on Mar 15, 2026

![Field & Stream Lodge Bozeman](https://images.trvl-media.com/lodging/109000000/108720000/108718800/108718730/50885963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Field & Stream Lodge Bozeman

CA $1,923

per person

Jun 8 - Jun 14

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Bozeman (BZN)

9/10 Wonderful! (338 reviews)

The rooms are set up really cool, outdoorsy vibe. We would come here again.

Reviewed on Mar 17, 2026

![Motel 6 Bozeman, MT](https://images.trvl-media.com/lodging/1000000/30000/21800/21701/dd4d2e25_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Motel 6 Bozeman, MT

CA $2,608

per person

Jun 8 - Jun 14

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Bozeman (BZN)

7/10 Good! (1,534 reviews)

Mold in bathrooms- allllll over

Reviewed on Mar 2, 2026

![Holiday Inn Express Hotel & Suites Belgrade by IHG](https://images.trvl-media.com/lodging/7000000/6230000/6228100/6228065/bf14aac6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express Hotel & Suites Belgrade by IHG

CA $1,899

per person

Jun 8 - Jun 14

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Bozeman (BZN)

9/10 Wonderful! (1,013 reviews)

Helpful front desk staff, easy and efficient shuttle service to/from airport and fresh biscuits for breakfast! Also two densities of pillows on all beds!!

Reviewed on Mar 15, 2026

![The Roosevelt Hotel - Yellowstone](https://images.trvl-media.com/lodging/23000000/22870000/22861500/22861453/f3b7b139_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Roosevelt Hotel - Yellowstone

CA $2,057

per person

Jun 8 - Jun 14

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Bozeman (BZN)

9/10 Wonderful! (1,149 reviews)

Better than I expect

Reviewed on Mar 10, 2026

## Wineglass Hotel Deals

![Fairfield Inn & Suites by Marriott Livingston Yellowstone](https://images.trvl-media.com/lodging/50000000/49110000/49101200/49101161/b85bf36e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fairfield Inn & Suites by Marriott Livingston Yellowstone

1629 West Park Street Livingston MT

Fully refundableReserve now, pay when you stay

CA $116

CA $128 total

Apr 2 - Apr 3

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=49101161&PinnedHotelID=49101161&HadPinnedHotel=true&regionId=553248635976480080)

![Wandering Buffalo](https://images.trvl-media.com/lodging/114000000/113400000/113396700/113396648/577c24ee_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wandering Buffalo

1200 E Main St Bozeman MT

Fully refundableReserve now, pay when you stay

CA $207

CA $226 total

Mar 24 - Mar 25

includes taxes & fees

9.2/10 Wonderful! (89 reviews)

The staff was tremendous. Very helpful. We loved the bikes. Bunk bed plus king is a nice set up.

Reviewed on Mar 15, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=113396648&PinnedHotelID=113396648&HadPinnedHotel=true&regionId=553248635976480080)

![Residence Inn by Marriott Bozeman Downtown](https://images.trvl-media.com/lodging/68000000/67550000/67546700/67546615/8498a844_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Residence Inn by Marriott Bozeman Downtown

815 East Main Street Bozeman MT

Fully refundableReserve now, pay when you stay

CA $231

CA $253 total

Mar 29 - Mar 30

includes taxes & fees

9.2/10 Wonderful! (446 reviews)

Nice hotel in great location.

Reviewed on Mar 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=67546615&PinnedHotelID=67546615&HadPinnedHotel=true&regionId=553248635976480080)

[See all 531 properties in Wineglass](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F03%2F2026&endDate=20%2F03%2F2026&regionId=553248635976480080)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Wineglass vacation package cost?

### How do I get a cheap travel package to Wineglass?

### How far in advance should I book my Wineglass vacation?

### What does an Expedia Wineglass travel package include?

### What should I know before booking a Wineglass travel package?

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

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

### 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 Livingston. While in this walkable area, you can savor the restaurants and breweries. 

[](https://expedia.ca/Livingston-Depot-Center-Historic-Livingston.d6115524.Vacation-Attraction)

### Things to do

![Private Yellowstone Winter Wolf Watching and Wildlife Safari ](https://mediaim.expedia.com/localexpert/1244740/86deeb11-a064-4e61-8c6b-69411d150ce4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Private Yellowstone Winter Wolf Watching and Wildlife Safari

CA $2,261

per traveller

[](https://expedia.ca/things-to-do/private-yellowstone-winter-wolf-watching-and-wildlife-safari.a1244740.activity-details)

[See all activities in Livingston](https://expedia.ca/things-to-do/search?rid=553248635976480080)

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