Roundup Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

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.
SureStay Plus Hotel by Best Western Billings

SureStay Plus Hotel by Best Western Billings

2.5 out of 5
per person
Oct 8 - Oct 11
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
8.8/10 Excellent! (1,000 reviews)
Floor plan not laid out well

Reviewed on Jul. 13, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
per person
Oct 8 - Oct 11
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
8/10 Very Good! (1,163 reviews)
Clean rooms. Nice people. Waterslides are fun!

Reviewed on Jul. 12, 2025

Northern Hotel

Northern Hotel

4 out of 5
per person
Oct 8 - Oct 11
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
9.4/10 Exceptional! (1,045 reviews)
Charming unique gym/ friendly could use updating

Reviewed on Jul. 15, 2025

La Quinta Inn & Suites by Wyndham Billings

La Quinta Inn & Suites by Wyndham Billings

3 out of 5
per person
Aug 16 - Aug 19
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
9/10 Wonderful! (1,097 reviews)
Everything so far has been great. I have no complaints.

Reviewed on Jul. 12, 2025

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
North Park
per person
Aug 16 - Aug 19
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Billings (BIL)
8.2/10 Very Good! (1,001 reviews)
Central location plenty of bars and restaurants.

Reviewed on Jun. 28, 2025

Ready to book your vacation to Roundup?

 

Choose your dates

Roundup Hotel Deals

Autumn's Inn
Autumn's Inn
2.5 out of 5
630 Main Street, Roundup, MT
The price is CA $93 per night from Jul 27 to Jul 28
CA $93
CA $100 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (123 reviews)
"Rooms are old, but kept clean and comfortable"

Reviewed on Jun. 30, 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 $724 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.