Roundup Vacation Packages

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Your Roundup Vacation

Well known for its small-town feel and friendly locals, Roundup is an excellent getaway destination. Book one of our Roundup vacation packages and discover all that this exciting city has to offer. If taking in sights is on the cards during your trip to Roundup, swing by major attractions like Musselshell Valley Historical Museum, Roundup City Park and Pine Ridge Golf Club. Expedia has what you need to escape your daily routine. Tailor your vacation to Roundup to match your travel style, whatever that may be!

Top Roundup Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Beartooth Hideaway Inn and Cabins

Beartooth Hideaway Inn and Cabins

2.5 out of 5
Price was CA $1,147, price is now CA $1,147 per person
CA $1,147
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9/10 Wonderful! (1,003 reviews)
We had a wonderful stay! Highly recommend!

Reviewed on Aug. 19, 2025

Chateau Rouge Condominiums

Chateau Rouge Condominiums

2 out of 5
Price was CA $1,488, price is now CA $1,356 per person
CA $1,356
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9/10 Wonderful! (178 reviews)
No air conditioning! At 1:00am girls singing and very disturbing!

Reviewed on Aug. 19, 2025

Quality Inn Red Lodge Gateway To Yellowstone

Quality Inn Red Lodge Gateway To Yellowstone

2.5 out of 5
Price was CA $1,390, price is now CA $1,291 per person
CA $1,291
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8.8/10 Excellent! (678 reviews)
We were at another property in red Lodge and changed to the quality Inn because the beds were so bad at the other location . at your property the beds were so comfy! Outstanding Thanks

Reviewed on Aug. 18, 2025

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Roundup Hotel Deals

Autumn's Inn

Autumn's Inn

2.5 out of 5
630 Main Street, Roundup, MT
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Sep 14 to Sep 15
CA $94
CA $101 total
Sep 14 - Sep 15
includes taxes & fees
8.2/10 Very Good! (136 reviews)
"Nice motel enjoyed are stay. Good food on site"

Reviewed on Aug. 15, 2025

Autumn's Inn
Roundup Cozy and Scenic Cabin Secluded and Scenic

Roundup Cozy and Scenic Cabin Secluded and Scenic

Roundup
Mostly positive.
"Was somewhat surprised by the lack of a toaster and minimal utensils. Listing said it sleeps 5 but found only 4 forks to use. Spoke to the host and asked if they had everything needed for cooking and kind of expected basic spices such as salt and pepper but found none. All else was as advertized ..."

Reviewed on Oct. 28, 2023

Get rates
Roundup Cozy and Scenic Cabin Secluded and Scenic
Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC

Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC

Billings
Get rates
Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC
See all 16 properties in Roundup
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Roundup vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,147 on Expedia. However, how much your vacation to Roundup costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Roundup?
January, March and November are the best times to search for cheap Roundup vacation packages. Travelling in quieter months means you'll typically find lower prices on flights and hotels.
How many days is enough for Roundup?
The ideal duration of your Roundup vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to go to all the main sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Roundup?
Roundup offers everything you need for an unforgettable escape. Get your Roundup vacation off to a flying start by checking out major attractions like Musselshell Valley Historical Museum.
How to find the best Roundup package deals?
Use Expedia's filters to find some unbeatable Roundup package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Roundup package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Roundup vacation as a package?
You can enjoy significant savings on your next Roundup break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Roundup?
If you're planning a spur-of-the-moment Roundup adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Roundup?

  1. Pick your travel dates: The things you'd like to do in Roundup and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like transportation, flights and meals when working out how much to save for your trip to Roundup. Then, select a hotel that matches your budget, whether that's an economical option or a lavish retreat.
  3. Set the duration of your trip: Start by listing all the attractions you want to get to in Roundup. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Roundup vacation package that brings all your bookings together.

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