Roundup Holiday Rentals

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Holiday Rentals in Roundup

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
Secluded Montana Getaway w/ Fire Pit & Views!
10.0 out of 10, Exceptional, (2)
"We loved the house. It was perfect for our group of 10. We loved the privacy and watching all the cattle. House was 8min from ryegates super d grocery store and it has almost everything you needed. Only thing we wish the yard was mowed down a bit off the back porch for the kids but over all we enjoyed our stay."
Secluded Montana Getaway w/ Fire Pit & Views!
Quiet Country Burnt Cross Cabin close to Billings
8.8 out of 10, Excellent, (3)
"Was clean and had everything we needed"
Quiet Country Burnt Cross Cabin close to Billings
See the stars from this cozy guest cabin 30 minutes from Billings.
10.0 out of 10, Exceptional, (2)
"We enjoyed two nights in this unique cabin 20 minutes outside Billings while visiting family in the area. Location was a bit out of the way but we enjoyed the peace and quiet and the road out there is a part of the adventure. Hosts were very accommodating and it has a perfect area for dogs to be let out securely. Would be happy to return."
See the stars from this cozy guest cabin 30 minutes from Billings.
Restored Vintage Mobile Home on our small Private Ranch
8.8 out of 10, Excellent, (6)
"Came as advertised. Rustic. Basic. Very pretty location."
The price is AU$269
includes taxes & fees
3 Dec - 4 Dec
Restored Vintage Mobile Home on our small Private Ranch
Tiny House in the country, close to Billings
9.6 out of 10, Exceptional, (5)
"Property as described Stacy was quick to answer any questions we had"
Tiny House in the country, close to Billings
Small Town Big Sky
10.0 out of 10, Exceptional, (3)
"Great open kitchen and living room for a large group to hang out we all enjoyed the stay"
Small Town Big Sky
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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Other types of properties in Roundup you may be interested in

Autumn's Inn
2.5 star property
8.2 out of 10, Very good, (103)
"Great spot to stay in MT"
The price is AU$124
includes taxes & fees
23 Nov - 24 Nov
Autumn's Inn
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
Big Sky Motel
2.0 star property
9.4 out of 10, Exceptional, (38)
"friendly staff, very accommodating."
Big Sky Motel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Roundup?

Yes, there are holiday rentals close to the most popular sights in Roundup, or you can select a more secluded option if you're looking for a relaxing stay. Roundup is known for its parks and museums.

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

Secluded Montana Getaway w/ Fire Pit & Views!: This holiday home rental outside of Roundup offers a patio, a selection of games and a BBQ 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 that 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 holiday rental in Roundup like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roundup. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family getaway.