Wineglass Holidays from AU$2,361

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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.
Field & Stream Lodge Bozeman

Field & Stream Lodge Bozeman

4 out of 5
Price was AU$2,705, price is now AU$2,361 per person
AU$2,361
per person
29 Mar - 5 Apr
found 4 hours ago
Return direct flight included
Sydney (SYD) to Bozeman (BZN)
9/10 Wonderful! (233 reviews)
Staff was very hospitable, especially in the restaurant Dry Fly Saloon/Honeyhole. Shoutout to waitress Sandy, she was awesome! Would have been nice if the pool/hottub was open, but they sent a message before hand. Great ski vacation for us! Very convenient location to town, ski mountain and airport.

Reviewed on 8 Jan 2026

320 Guest Ranch

320 Guest Ranch

3 out of 5
Price was AU$3,138, price is now AU$2,739 per person
AU$2,739
per person
29 Mar - 5 Apr
found 4 hours ago
Return direct flight included
Sydney (SYD) to Bozeman (BZN)
9.4/10 Exceptional! (1,000 reviews)
Everything was great! The hotel was clean, comfortable, and well maintained. The staff was friendly and helpful, and the overall experience was excellent.

Reviewed on 8 Jan 2026

RSVP Hotel

RSVP Hotel

3.5 out of 5
Midtown
Price was AU$2,864, price is now AU$2,542 per person
AU$2,542
per person
29 Mar - 5 Apr
found 4 hours ago
Return direct flight included
Sydney (SYD) to Bozeman (BZN)
9.4/10 Exceptional! (1,005 reviews)
This place was adorable, I loved all the little touches especially the garnet and champagne. Can’t wait to stay again

Reviewed on 10 Jan 2026

The LARK Bozeman

The LARK Bozeman

3 out of 5
Downtown Bozeman
Price was AU$2,978, price is now AU$2,664 per person
AU$2,664
per person
29 Mar - 5 Apr
found 4 hours ago
Return direct flight included
Sydney (SYD) to Bozeman (BZN)
9.4/10 Exceptional! (1,007 reviews)
Good area nice staff. Room didn’t have a fridge or anything though. Kind of a drag

Reviewed on 10 Jan 2026

Wandering Buffalo

Wandering Buffalo

3 out of 5
Price was AU$2,719, price is now AU$2,442 per person
AU$2,442
per person
29 Mar - 5 Apr
found 4 hours ago
Return direct flight included
Sydney (SYD) to Bozeman (BZN)
9.6/10 Exceptional! (51 reviews)
Fun place to stay. Very helpful and friendly staff.

Reviewed on 30 Dec 2025

Our pick of the best Wineglass Hotel Deals

Residence Inn by Marriott Bozeman Downtown

Residence Inn by Marriott Bozeman Downtown

3 out of 5
815 East Main Street Bozeman MT
The price is AU$248 per night from 13 Jan to 14 Jan
AU$248
13 Jan - 14 Jan
includes taxes & fees
9.2/10 Wonderful! (413 reviews)
Front desk staff- ava was awesome

Reviewed on 8 Jan 2026

Residence Inn by Marriott Bozeman Downtown
Fairfield Inn & Suites by Marriott Livingston Yellowstone

Fairfield Inn & Suites by Marriott Livingston Yellowstone

2.5 out of 5
1629 West Park Street Livingston MT
Fully refundableReserve now, pay when you stay
The price is AU$128 per night from 16 Jan to 17 Jan
AU$128
16 Jan - 17 Jan
includes taxes & fees
9.4/10 Exceptional! (650 reviews)
Clean and fun

Reviewed on 28 Dec 2025

Fairfield Inn & Suites by Marriott Livingston 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 AU$109 per night from 19 Jan to 20 Jan
AU$109
19 Jan - 20 Jan
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
Rating was based on renovations that limited services.

Reviewed on 6 Jan 2026

Yellowstone River Inn & Suites
See all 518 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Wineglass holiday package cost?
The most affordable Wineglass package is AU$2,361, 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 holiday packages promise plenty of savings for the savvy traveller. 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 holiday package here just for you.
How far in advance should I book my Wineglass holiday?
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 holiday homes like mountain cabins and serviced residences. You've got choices galore!
Can I choose my airline with a Wineglass Expedia holiday 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 holiday package?
Yes, you can. We realise even the best-laid plans can go awry, so we're happy to help if you need to make changes to your Wineglass holiday 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

KPRK Radio

Learn about the local history of Livingston when you spend time at KPRK Radio. Savour the area's cafes and breweries.

KPRK Radio

Activities

Private Yellowstone Winter Wolf Watching and Wildlife Safari

Private Yellowstone Winter Wolf Watching and Wildlife Safari

AU$2,465
per traveller
Private Yellowstone Winter Wolf Watching and Wildlife Safari
See all activities in Livingston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.