Roundup Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Roundup

Our top choices for Roundup vacation rentals

Roundup Cozy and Scenic Cabin Secluded and Scenic
Exterior

Roundup Cozy and Scenic Cabin Secluded and Scenic

8.0 out of 10, Very good, (1)
"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 except for the visits at night by rodents which ate almost a half roll of bathroom tissue! Owners were very friendly and helpful! Addition of a hanging rack for big game would be helpful if hunters stay...
Roundup Cozy and Scenic Cabin Secluded and Scenic
Restored Vintage Mobile Home on our small Private Ranch
Exterior

Restored Vintage Mobile Home on our small Private Ranch

9.0 out of 10, Wonderful, (8)
"Perfect lodging for our trip. Kurt was very responsive and hospitable. We will certainly be back on future trips to the area."
The price is CA $110
CA $237 total
includes taxes & fees
Sep 1 - Sep 2
Restored Vintage Mobile Home on our small Private Ranch
Quiet Country Burnt Cross Cabin close to Billings
Interior

Quiet Country Burnt Cross Cabin close to Billings

9.4 out of 10, Exceptional, (6)
"Was clean and had everything we needed"
Quiet Country Burnt Cross Cabin close to Billings
Tiny House in the country, close to Billings
Fridge, microwave, oven, stovetop

Tiny House in the country, close to Billings

9.6 out of 10, Exceptional, (5)
"Exactly what I needed. A very charming place and extremely reasonable. I will definitely look for another stay there. Highly recommended for short and long stays. Thank you for a relaxing space."
Tiny House in the country, close to Billings
Near Hunting: Cozy Cabin w/ Deck in Grass Range!
House (1 Bedroom) | Interior

Near Hunting: Cozy Cabin w/ Deck in Grass Range!

3.0 star property
Near Hunting: Cozy Cabin w/ Deck in Grass Range!
See the stars from this cozy guest cabin 30 minutes from Billings.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"The owners live on property and they're the sweetest people, they have the nicest dogs and made sure it was okay if they were around. The owners made sure we had everything we needed. We will definitely be back!"
See the stars from this cozy guest cabin 30 minutes from Billings.
Small Town Big Sky
Fridge, microwave, oven, stovetop

Small Town Big Sky

9.4 out of 10, Exceptional, (6)
"Great open kitchen and living room for a large group to hang out we all enjoyed the stay"
Small Town Big Sky
Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC
1 bedroom, desk, WiFi, bed sheets

Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC

Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC
Charming bungalow with AC and WiFi in a private rural part of Billings.
Exterior detail

Charming bungalow with AC and WiFi in a private rural part of Billings.

Charming bungalow with AC and WiFi in a private rural part of Billings.
3 Bedroom 2 bath with space for classes and retreats
Terrace/patio

3 Bedroom 2 bath with space for classes and retreats

3 Bedroom 2 bath with space for classes and retreats
Secluded Montana Getaway w/ Fire Pit & Views!
House (6 Bedrooms) | Interior

Secluded Montana Getaway w/ Fire Pit & Views!

3.0 star property
Secluded Montana Getaway w/ Fire Pit & Views!
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.
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Top Roundup Hotel Reviews

Find out more about Roundup

Find out more about Roundup

Everything you need to know about Roundup vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Roundup vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Roundup vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Roundup vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Roundup. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Roundup vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Roundup vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Roundup rentals

At Expedia, we put the best Roundup vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Roundup rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Roundup vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Roundup. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Roundup?

Yes, there are vacation rentals close to top sights in Roundup, or you can select a more remote option if you're looking for a relaxing stay. Roundup is known for its parks and museums.

What are some of the best vacation home rentals that Roundup has to offer?

Secluded Montana Getaway w/ Fire Pit & Views!: This vacation home rental outside of Roundup offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Roundup?

Cultural attractions include Musselshell Valley Historical Museum, whereas Roundup City Park is a spot to enjoy nature. Other places in town to visit include Pine Ridge Golf Club.

What’s a vacation rental in Roundup like?

Vacation rentals are private properties you can stay in for a long or short time in Roundup. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.