Roundup Vacations from $360

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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.
Western Executive Inn

Western Executive Inn

2.5 out of 5
West End
Price was $417, price is now $360 per person
$360
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Billings (BIL)
8/10 Very Good! (324 reviews)
We thought it was closed when we pulled up - big delivery of boxes in the checkin area no one present man cleaning the floor checked us in - carpet old and dirty

Reviewed on Jul 14, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Save 100% on your flight
Price was $1,021, price is now $585 per person
$585
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Billings (BIL)
8.2/10 Very Good! (1,640 reviews)
Pretty run down

Reviewed on Jul 13, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $628, price is now $519 per person
$519
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Billings (BIL)
9.6/10 Exceptional! (1,221 reviews)
Our stay was excellent. Every staff member wad kind and accommodating. Our room was perfectly clean and well stocked. We do wish there had been a fridge in the room, but it didnt affect the pleasant experience we had. We enjoyed an exceptional breakfast at Bernies to end our stay.

Reviewed on Jul 12, 2026

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $732, price is now $615 per person
$615
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
9.8/10 Exceptional! (107 reviews)
Family friendly or a fantastic couples retreat. The grounds were incredible and the surrounding area was majestic. Highly recommend.

Reviewed on Jul 8, 2026

Days Inn by Wyndham Billings

Days Inn by Wyndham Billings

2 out of 5
Southwest Corridor
Price was $524, price is now $451 per person
$451
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Billings (BIL)
8.2/10 Very Good! (1,335 reviews)
Stayed here for the first time and it was okay

Reviewed on Jul 13, 2026

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Stay near popular Roundup attractions

Roundup City Park

8.0/10 (5 reviews)
This vibrant community space offers a free public swimming pool, tennis courts, and modern playground in the heart of Roundup. Summer visitors can enjoy the park during the annual Independence Days Extravaganza.
See properties

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
$75 nightly
The price is $81 total per night from Jul 15 to Jul 16
$81 total
Jul 15 - Jul 16
Total with taxes and fees
8.4/10 Very Good! (161 reviews)
"Our A/c was not working well and read a code and we went to tell staff no one around. We left a note and our a/c still had the code on it when we left."

Reviewed on Jun 27, 2026

Autumn's Inn
Montana Country Retreat w/ Hot Tub-Near Lewistown

Montana Country Retreat w/ Hot Tub-Near Lewistown

Grass Range MT
10/10 Exceptional! (3 reviews)
"Great fenced yard, clean, and beautiful setting. Hot tub was amazing!"

Reviewed on May 15, 2026

Get rates
Montana Country Retreat w/ Hot Tub-Near Lewistown
See the stars from this cozy guest cabin 30 minutes from Billings.

See the stars from this cozy guest cabin 30 minutes from Billings.

Shepherd MT
10/10 Exceptional! (4 reviews)
"I got to check in early, host was checking in to make sure we were comfortable, 10/10 would totally stay again. It was nice to see all the the wildlife. It was very quiet. Beautiful at night."

Reviewed on Jul 8, 2026

Get rates
See the stars from this cozy guest cabin 30 minutes from Billings.
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.

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

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Frequently asked questions

How much does a Roundup vacation package cost?
You can snap up a vacation package to this destination from $360 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?
You can usually find lower rates and better availability in January, March and October. Browse our cheap Roundup vacation packages and you could score some great off-season deals.
How many days is enough for Roundup?
With a well-organized itinerary, you can easily hit the top Roundup attractions in a handful of days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Roundup vacation for longer.
Is it worth booking a vacation package to Roundup?
It's no wonder a Roundup vacation is on the to-do list of many travelers. Major attractions like Roundup City Park are just the beginning of things to keep you busy here.
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.
Does Expedia offer Book Now, Pay Later Roundup vacation packages?
Your Roundup trip is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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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.