Roundup Vacation Rentals from CA $110: Short-Term Rentals for 2025

Q: 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.

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Vacation Rentals in Roundup

Situated in a rural setting, this cabin features a front door and two windows.

"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...

Cozy retreat with a traditional bed, carpeted floor, and mounted TV.

Enjoy meals at the large dining table with six chairs, surrounded by ample counter space and an island.

"We stayed here because our church was having a retreat about 20 miles away at a camp facility. Know we weren't the rough it type we booked this great house. Everything was fantastic. Only wish we would have had more time at the property. We will stay here again for sure."

Compact kitchen with a refrigerator, pantry door, and wooden walls.

"Was clean and had everything we needed"

Enjoy meals in the kitchen with a central island and dining table near a window offering a view of the surrounding landscape.

"This was the perfect little cabin for our girls weekend turkey hunting trip. Clean, so cute and even greeted with homemade brownies, thanks Angie!"

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a large dining table.

Situated in a serene grassy field, this single-story building offers a simple, peaceful retreat.

"Perfect lodging for our trip. Kurt was very responsive and hospitable. We will certainly be back on future trips to the area."

CA $237 total

includes taxes & fees

Jul 17 - Jul 18

Enjoy cooking in this well-equipped kitchen with a dishwasher, oven, and coffee maker.

"Great open kitchen and living room for a large group to hang out we all enjoyed the stay"

Kitchen with a stainless steel sink, ventilation, and a window for natural light.

"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."

Cozy kitchen with white cabinetry, microwave, and gas stove.

"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!"

Enjoy cooking in this well-equipped kitchen with an oven, dishwasher, and ample workspace.

Enjoy a serene outdoor space with a round table, chairs, and a fire pit, surrounded by a tree and offering a clear view of the surrounding landscape.

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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.

Recent reviews of Roundup properties

Quiet Country Burnt Cross Cabin close to Billings

5/5 Excellent

Very cozy

"Perfect little space that my son and I were looking for on our vacation adventure. Quiet, cute and necessities that we were wanting for the trip. We would definitely stay again in our journeys take us to the area. Thank you!"

A verified traveller stayed at Quiet Country Burnt Cross Cabin close to Billings

Posted 10 days ago

3/5 Okay

Perfect Location

"The location was absolutely perfect for what we needed. The main room was huge; big enough for all 16 of our group to meet and plan. Five bedrooms, sleep space for 10. The beds were hard as a rock (or plywood, probably). If you like that, you'll love this place! 2 bathrooms with showers - the second of which was not mentioned in the listing. Very nice surprise, since we ended up with 7 staying there. It was very basic but had everything needed for our stay.Everyone in the very small town was friendly. "

A verified traveller stayed at Small Town Big Sky

Posted 2 months ago

Secluded Montana Getaway w/ Fire Pit & Views!

5/5 Excellent

Family vacation

"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."

A verified traveller stayed at Secluded Montana Getaway w/ Fire Pit & Views!

Posted 1 year ago

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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.

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Roundup Vacation Rentals

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Vacation Rentals in Roundup

Roundup Cozy and Scenic Cabin Secluded and Scenic

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

Secluded Montana Getaway w/ Fire Pit & Views!

Quiet Country Burnt Cross Cabin close to Billings

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

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

Restored Vintage Mobile Home on our small Private Ranch

Small Town Big Sky

Tiny House in the country, close to Billings

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

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

3 Bedroom 2 bath with space for classes and retreats

Secluded Montana Getaway w/ Fire Pit & Views!

Find out more about Roundup

Recent reviews of Roundup properties

Quiet Country Burnt Cross Cabin close to Billings

Autumn's Inn

Small Town Big Sky

Restored Vintage Mobile Home on our small Private Ranch

Secluded Montana Getaway w/ Fire Pit & Views!

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