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
Feb. 24 - Mar. 3
found 1 day ago
Roundtrip flight included
Regina (YQR) to Billings (BIL)
9.2/10 Wonderful! (1,003 reviews)
I like the fact that itis very close to the clinic/hospital. Also that it's well maintained and the fact that they were right on top of the snow.

Reviewed on Jan. 7, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
per person
Feb. 10 - Feb. 17
found 24 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
8/10 Very Good! (1,006 reviews)
Amazing Honeymoon Suite.

Reviewed on Jan. 6, 2025

SureStay Plus Hotel by Best Western Billings

SureStay Plus Hotel by Best Western Billings

2.5 out of 5
per person
Feb. 24 - Mar. 3
found 1 day ago
Roundtrip flight included
Regina (YQR) to Billings (BIL)
8.8/10 Excellent! (1,001 reviews)
Easy to find. Was good for the price

Reviewed on Jan. 8, 2025

Hilltop Inn by Riversage

Hilltop Inn by Riversage

3 out of 5
per person
Feb. 24 - Mar. 3
found 1 day ago
Roundtrip flight included
Regina (YQR) to Billings (BIL)
9/10 Wonderful! (1,314 reviews)
Clean and comfortable stay.

Reviewed on Jan. 5, 2025

Country Inn & Suites by Radisson, Billings, MT

Country Inn & Suites by Radisson, Billings, MT

3 out of 5
per person
Feb. 24 - Mar. 3
found 1 day ago
Roundtrip flight included
Regina (YQR) to Billings (BIL)
8.4/10 Very Good! (1,002 reviews)
I’ve stayed at this hotel 4 times this year when I come to visit family I’ve stayed with just me and my girlfriend and also us and are 3 kids and every time was great no issues very helpful the free breakfast every morning was fresh and they had a good amount of options to pick from and it’s wicked helpful when you have the kids with you the hot tub and pool was clean and fun for the kids and adults it’s 5 minutes from the airport and a bunch of stores we will stay here many more times to come

Reviewed on Dec. 30, 2024

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 $77 per night from Jan. 23 to Jan. 24
CA $77
CA $84 total
includes taxes & fees
Jan 23 - Jan 24
8/10 Very Good! (105 reviews)
"Great staff, clean room, nice breakfast"

Reviewed on Jan. 2, 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
Big Sky Motel
Big Sky Motel
2 out of 5
740 Main St, Roundup, MT
9.4/10 Exceptional! (38 reviews)
"friendly staff, very accommodating."

Reviewed on Jan. 16, 2023

Get rates
Big Sky Motel
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

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 destination from CA $1,342 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.

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