Roundup Vacations from $423
Book a Hotel + Flight or Car together to unlock savings
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.
Ledgestone Suites Hotel Billings
Price was $467, price is now $423 per person
$423
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Ontario (ONT) to Billings (BIL)
9.4/10 Exceptional! (1,313 reviews)
Pillows and mattress were to my liking. Lobby stunk a little but room was very clean and smell free.
Reviewed on Oct 22, 2025
Billings Hotel and Convention Center
Price was $992, price is now $818 per person
$818
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip flight included
Ontario (ONT) to Billings (BIL)
8/10 Very Good! (1,324 reviews)
Definitely oversold through the pictures. This hotel was a two-star at best, people living in vehicles in the back parking lot, dirty and disrepair everywhere, very plain worn rooms, a filthy dirty dark pool area that brought to mind images of a horror movie. Not a place to stay again, would not recommend. We got duped
Reviewed on Oct 21, 2025
La Quinta Inn & Suites by Wyndham Billings
Price was $918, price is now $832 per person
$832
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip flight included
Ontario (ONT) to Billings (BIL)
9/10 Wonderful! (1,201 reviews)
Very friendly front desk, really enjoyed the PM managers, made us feel taken care of.
Reviewed on Oct 21, 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
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $81 total per night from Nov 13 to Nov 14
$81 total
Nov 13 - Nov 14
Total with taxes and fees
8.4/10 Very Good! (145 reviews)
really enjoyed my stay. the owners were very friendly and helpful.
Reviewed on Oct 17, 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.
Find the Best Roundup Vacation Packages
Roundup Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,850 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Musselshell Valley Historical Museum, Roundup City Park and Pine Ridge Golf Club |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Roundup City Park
- Hotels near Pine Ridge Golf Club
- Klein Hotels
- Lavina Hotels
- Broadview Hotels
- Melstone Hotels
- 4 Star Hotels in Melstone
- 5 Star Hotels in Melstone
- Ryegate Hotels
- Shepherd Hotels
- 5 Star Hotels in Shepherd
- B&B in Shepherd
- Worden Hotels
- 4 Star Hotels in Worden
- Hotels near Town & Country Lanes and Lounge
- Winnett Hotels
- Cabin Rentals in Winnett
- 5 Star Hotels in Winnett
- Ballantine Hotels
- Huntley Hotels
- Vacation Homes in Huntley
- Motels in Huntley
- Hotels near Pompeys Pillar National Monument
- Billings Hotels
- Grass Range Hotels
- Hotels near Lake Elmo State Park
- Hotels near Billings Heights
- Lockwood Hotels
- Hotels near Logan Intl.
- Hotels near Rimrock
- Flights from Broadview
- Flights to Melstone
- Flights to Golden Valley County
- Flights from Ryegate
- Flights to Shepherd
- Flights from Shepherd
- Flights from Acton
- Flights to Worden
- Flights from Worden
- Flights to Winnett
- Flights to Huntley
- Flights from Huntley
- Flights to Billings
- Flights from Denver (DEN) to Billings (BIL)
- Flights from Phoenix (PHX) to Billings (BIL)
- Flights from Seattle (SEA) to Billings (BIL)
- Flights from Portland (PDX) to Billings (BIL)
- Flights from Minneapolis (MSP) to Billings (BIL)
- Flights from Salt Lake City (SLC) to Billings (BIL)
- Flights from Bozeman (BZN) to Billings (BIL)
- Flights from Missoula (MSO) to Billings (BIL)
- Flights from Houston (IAH) to Billings (BIL)
- Flights from Spokane (GEG) to Billings (BIL)
- Flights from Dallas (DFW) to Billings (BIL)
- Flights from Boise (BOI) to Billings (BIL)
- Flights from Las Vegas (LAS) to Billings (BIL)
- Flights from Orlando (MCO) to Billings (BIL)
- Flights from Chicago (ORD) to Billings (BIL)
- Flights from San Diego (SAN) to Billings (BIL)
- Flights from Los Angeles (LAX) to Billings (BIL)
- Flights from Atlanta (ATL) to Billings (BIL)
- Flights from Reno (RNO) to Billings (BIL)
- Flights from Great Falls (GTF) to Billings (BIL)
- Flights from Kalispell (FCA) to Billings (BIL)
- Flights from Detroit (DTW) to Billings (BIL)
- Flights from Sacramento (SMF) to Billings (BIL)
- Flights from Sioux Falls (FSD) to Billings (BIL)
- Flights from Fargo (FAR) to Billings (BIL)
- Flights from Tucson (TUS) to Billings (BIL)
- Flights from Columbus (CMH) to Billings (BIL)
- Flights from St. Louis (STL) to Billings (BIL)
- Flights from Rapid City (RAP) to Billings (BIL)
- Flights from Raleigh (RDU) to Billings (BIL)
- Flights from Austin (AUS) to Billings (BIL)
- Flights from Nashville (BNA) to Billings (BIL)
- Flights from Helena (HLN) to Billings (BIL)
- Flights from Bismarck (BIS) to Billings (BIL)
- Flights from Tampa (TPA) to Billings (BIL)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.