Roundup Holidays from £1,163
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Your Roundup Holiday
Well known for its small-town feel and friendly locals, Roundup is an excellent getaway destination. Book one of our Roundup holiday 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 holiday to Roundup to match your travel style, whatever that may be!
Top Roundup Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Dude Rancher Lodge
Downtown Billings
£1,236
per person
19 Sept - 26 Sept
found 14 hours ago
Return flight included
London (LGW) to Billings (BIL)
8.6/10 Excellent! (1,291 reviews)
A place with personality, not your typical cookie-cutter chain hotel! Check-in was smooth and the person that helped us was efficient and pleasant. Room was clean and comfortable. Having a door on each end of the room is a bit odd, and parking is a bit limited. At first we thought it might be noisy, but wasn't. We slept well. Since it's downtown, there are lots of restaurants within walking distance. We felt comfortable walking around in the evening and again in the morning. Seemed to be a good value for the Billings area.
Reviewed on 19 Aug 2026
Roundup Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,850 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Musselshell Valley Historical Museum, Pine Ridge Golf Club and Roundup City Park |
Top hotels in Roundup
Autumn's Inn
630 Main Street Roundup MT
Fully refundableReserve now, pay when you stay
£54
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very good! (173 reviews)
"Would like to have had more blankets on the bed."
Reviewed on 17 Aug 2026
Tiny House in the country, close to Billings
Worden MT
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 8 Jul 2026
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.
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.
Pine Ridge Golf Club
8.0/10 (2 reviews)
This relaxed 9-hole public course offers bluegrass fairways and bentgrass greens amid Montana's scenic landscape. Enjoy a straightforward yet satisfying round that welcomes golfers of all skill levels.
Musselshell Valley Historical Museum
8.0/10 (2 reviews)
This intimate museum chronicles Montana's coal mining past and early settler life through authentic artefacts. Explore the original 1884 log cabin and replica coal mine shaft for a glimpse into frontier history.
Frequently asked questions
Why should I book my Roundup holiday with Expedia?
With excellent-value flights, car hire and accommodation options all in one convenient place, Expedia makes planning your Roundup break a cinch. Plus, we can help you bundle your bookings into a package holiday so you can save even more. Select from fabulous stays, add flights and/or a hire car (and maybe also some exciting activities!) and land incredible prices. Need to change your plans? Expedia offers a flexible cancellation policy for many reservations. To discover more, make your way to our Customer Service Portal link.
When is the best time of year to holiday in Roundup?
To enjoy the atmosphere of peak season, pack your bags for April, June and July. January, March and October are generally quieter and a good idea if you'd rather escape the crowds. With daytime average temperatures of -4ºC, February is the coolest period in Roundup. The warmest month is July, when you can experience averages of 23ºC throughout the day. Whatever the temperature, you'll discover loads to keep you entertained here.
What is the top hotel for my holiday in Roundup?
Offering plenty of amenities and home comforts, Big Sky Motel will make an ideal base for your Roundup holiday.
How do I get a cheap holiday to Roundup?
Book everything in the one place with our Roundup holidays. We have incredible bargains on flights, hotels, tours and more that'll keep your wallet happy and adventurous side satisfied. And, with more than 400 partner airlines and 321,000 hotels all over the world to select from, you'll have the flexibility to mix and match all you want. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Roundup holiday?
Make sure your next holiday in Roundup is a memorable one by checking out its major attractions. Roundup City Park, Musselshell Valley Historical Museum, Roundup Memorial Healthcare and Pine Ridge Golf Club are some of the things we recommend seeing while you're in the city.
What is the best area to stay in when on holiday in Roundup?
A trip to Roundup isn't complete without seeing Roundup City Park. Why not book a stay near this interesting attraction?
Do I need a visa for my Roundup holiday?
Look up the most up-to-date information on official government websites. Your nationality and whether you're travelling for work or pleasure will determine if you'll require a visa for Roundup. Make yourself familiar with the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow enough time for processing. Some visas can take many weeks or even months to obtain, depending on the country.
What should I wear on my Roundup holiday?
Although everyone's style differs, it can help to have a few guidelines for what kind of clothes to wear during your holiday in Roundup. Consider looking up social media before leaving so you can blend in like a local. Daytime temperatures in February, Roundup's coolest month, average around -4ºC. July marks this destination's warmest month when the average temperature reaches 23ºC. Our top piece of advice? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Roundup holiday include?
Flights, hotels and a reliable car for your road trip adventures. Simply mix and match your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and activities and watch your savings pile up. When it comes to organising your Roundup break, you're in charge! Cabins and private holiday homes are a couple of the most sought-after property types in Roundup. Whatever your group size or holiday style, you can count on Expedia for the freedom and flexibility to customise your escape.
Does Expedia offer Book Now, Pay Later Roundup holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all types of budgets, so you can lock in that well-deserved holiday sooner.
- No-deposit holidays: Clicking the "book now" button is much easier with this plan. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel plans.
Can I choose my airline with a Roundup Expedia holiday?
Yes — that's one of the best things about an Expedia holiday package. You're the boss! We have access to more than 400 partner airlines all over the world, so you have lots of choice when organising your Roundup trip.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
