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.
Riversage Billings Inn

Riversage Billings Inn

3 out of 5
per person
Apr. 22 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.2/10 Wonderful! (1,004 reviews)
Comfortable room. Nice breakfast with cooked options!

Reviewed on Mar. 11, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
per person
Apr. 22 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8/10 Very Good! (1,039 reviews)
access to room sucked---No parking close to room

Reviewed on Mar. 10, 2025

Northern Hotel

Northern Hotel

4 out of 5
per person
Apr. 22 - Apr. 26
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.4/10 Exceptional! (1,006 reviews)
Staff was arrogant. No pool. Loud traffic noise

Reviewed on Mar. 10, 2025

Chateau Rouge Condominiums

Chateau Rouge Condominiums

2 out of 5
per person
May 24 - May 31
found 24 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.2/10 Wonderful! (106 reviews)
Chateau Rouge was clean and comfortable. It was exactly what we were looking for.

Reviewed on Mar. 8, 2025

SureStay Plus Hotel by Best Western Billings

SureStay Plus Hotel by Best Western Billings

2.5 out of 5
per person
May 4 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8.8/10 Excellent! (1,003 reviews)
Ran out of hot water one morning and construction in front of motel to get off highway

Reviewed on Mar. 8, 2025

Ready to book your vacation to Roundup?

 

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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 $78 per night from Mar. 26 to Mar. 27
CA $78
CA $84 total
includes taxes & fees
Mar 26 - Mar 27
8/10 Very Good! (109 reviews)
"The general population of people in Round up are so wonderful. This holds true at Autumn's Inn. The rooms are a little dated, but clean and well kept. Lots of pillows and the beds were comfortable. My only feedback is the heater unit was a touch on the loud side when it cycled. I do prefer background ..."

Reviewed on Feb. 18, 2025

Autumn's Inn
Roundup Cozy and Scenic Cabin Secluded and Scenic
Roundup Cozy and Scenic Cabin Secluded and Scenic
Roundup
8/10 Very Good! (1 review)
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

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Roundup Cozy and Scenic Cabin Secluded and Scenic
Small Town Big Sky
Small Town Big Sky
Winnett
10/10 Exceptional! (3 reviews)
Perfect place to stay in that area
"Great open kitchen and living room for a large group to hang out we all enjoyed the stay"

Reviewed on Nov. 21, 2023

Get rates
Small Town Big Sky
See all 15 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

Frequently asked questions

How much does a Roundup vacation package cost?
You can snap up a vacation package to this destination from CA $774 on Expedia. But 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?
If you’re looking to score a cheap Roundup vacation package, consider visiting in January, March and November. You’ll usually find lower prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Roundup?
Usually, a handful of days is enough to explore the top sights during your Roundup vacation. However, if you want to have more time to relax or go on day tours, think about extending your trip.
Is it worth booking a vacation package to Roundup?
Roundup has everything you need for an unforgettable trip. Begin your Roundup vacation on a high note by visiting popular attractions like Musselshell Valley Historical Museum.
How to find the best Roundup package deals?
Start your search for a Roundup package deal by entering your preferred travel dates and destination under our “Packages” tab. Then add some filters, like “Popular locations” and “Property type,” to tailor the results to your exact style. You can also sort by “Package discount” and browse offers that come with big savings. If you don’t find the perfect Roundup package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Roundup escape off to a flying start.
Is it cheaper to book a Roundup vacation as a package?
You can enjoy significant savings on your next Roundup break by booking a tailored vacation package. Click on the “Package” heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental 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 getaway, check out our last-minute deals that can be booked up to one week before you go. Don’t want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Roundup?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to vacation in Roundup.
  2. Budget wisely: On top of the cost of your hotel, you’ll need to consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Roundup.
  3. Set the duration of your trip: Start by compiling a list of the attractions you’d like to experience in Roundup. Then, estimate how long you’ll need for each, including any travel time.
  4. Bundle your airfare and accommodations: Once you’ve settled on your trip dates and duration, lock in the ideal Roundup vacation package for you.