Roundup Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

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

Find the Best Roundup Vacation Packages

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 ￥9,976 per night from Aug 21 to Aug 22
￥9,976
￥10,774 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (134 reviews)
"We felt very welcomed by the staff. A wonderful small town feel!"

Reviewed on Aug 7, 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.

Frequently asked questions

How much does a Roundup vacation package cost?
You can snap up a vacation package to this destination 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.