Roundup Vacations from $398
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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!
The Latest Roundup vacation packages
Price found within the past 48 hours. Click for updated prices.
Comfort Suites Billings
Price was $457, price is now $398 per person
$398
per person
Nov 21 - Nov 24
found 4 hours ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
8.4/10 Very Good! (1,005 reviews)
I chose that hotel because Expedia said it had free airport shuttle. After I checked in, I found out that they don't offer a shuttle! Too late to go somewhere else! The desk clerk said that they have repeatedly notified Expedia of the error.
Cost me $30 for transportation to airport.
Should I rely on Expedia from now on?
Reviewed on Sep 28, 2025
Northern Hotel
Price was $964, price is now $826 per person
$826
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Billings (BIL)
9.6/10 Exceptional! (1,100 reviews)
This was our first time in Montana. Staff was friendly facility was great.
Reviewed on Sep 28, 2025
DoubleTree by Hilton Hotel Billings
North Park
Price was $512, price is now $459 per person
$459
per person
Nov 21 - Nov 24
found 4 hours ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
8.2/10 Very Good! (1,003 reviews)
This a very comfortable and well-run hotel in the heart of the entertainment district in downtown Billings. The rooms are spacious, the amenities are generous, and the staff is pleasant and attentive.
Reviewed on Sep 28, 2025
Discover the most popular places to visit in Roundup
Roundup City Park
Explore the great outdoors at Roundup City Park, a lovely green space in Roundup. Take in the museums while you're in the area.
Pine Ridge Golf Club
Enjoy a round of golf in Camp Three at Pine Ridge Golf Club. Amble around the area's parks or experience its museums.
Musselshell Valley Historical Museum
You can browse the exhibits at Musselshell Valley Historical Museum, a museum with a storied past, during your trip to Roundup. Amble around the area's parks or experience its museums.
Roundup Hotel Deals
Autumn's Inn
630 Main Street, Roundup, MT
$75 nightly
The price is $81 total per night from Oct 16 to Oct 17
$81 total
Oct 16 - Oct 17
Total with taxes and fees
8.2/10 Very Good! (142 reviews)
"No options for eating dinner,"
Reviewed on Sep 22, 2025
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
Quiet Country Burnt Cross Cabin close to Billings
Worden
9.4/10 Exceptional! (6 reviews)
"Absolutely darling place that had everything I needed for my stay. The house was clean and the bed was very comfortable. The host was very nice and helpful and easy to get ahold of. Would highly recommend staying here!"
Reviewed on Jul 22, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.