Roundup Vacation Rentals

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Nov 9 - Nov 10
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Vacation Rentals in Roundup

Interior
Quiet Country Burnt Cross Cabin close to Billings

Quiet Country Burnt Cross Cabin close to Billings

Worden
9.4 out of 10, Exceptional, (6)
"Absolutely darling place that had everything I needed for my stay. The house was clean and the bed was very comfortable. The host was very nice and helpful and easy to get ahold of. Would highly recommend staying here!"
United States
Katie g.
Quiet Country Burnt Cross Cabin close to Billings
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

Billings
10.0 out of 10, Exceptional, (1)
"Great place had everything I needed! Easy to communicate with and would definitely recommend to anyone coming to Billings! Will stay here again if I have a chance."
United States
AJs D.
Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC
House (1 Bedroom) | Interior
Near Hunting: Cozy Cabin w/ Deck in Grass Range!

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

3.0 star property
Grass Range
Near Hunting: Cozy Cabin w/ Deck in Grass Range!
Fridge, microwave, oven, stovetop
Tiny House in the country, close to Billings

Tiny House in the country, close to Billings

Worden
9.6 out of 10, Exceptional, (5)
"Property as described Stacy was quick to answer any questions we had"
United States
Dianne W.
Tiny House in the country, close to Billings
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (3)
"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."
United States
Grady B.
See the stars from this cozy guest cabin 30 minutes from Billings.
Exterior
Restored Vintage Mobile Home on our small Private Ranch

Restored Vintage Mobile Home on our small Private Ranch

Lavina
9.0 out of 10, Wonderful, (8)
"We loved the property. The only one thing I can say that made us nervous was the loose dogs. They do seem a little scary. Thank you though for the lovely place in the woods."
United States
Jen C.
$160 nightly
The price is $173
Dec 2 - Dec 3
Total with taxes and fees
Restored Vintage Mobile Home on our small Private Ranch
Fridge, microwave, oven, stovetop
Small Town Big Sky

Small Town Big Sky

Winnett
9.6 out of 10, Exceptional, (7)
"Great open kitchen and living room for a large group to hang out we all enjoyed the stay"
United States
Shawna K.
Small Town Big Sky
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.

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

3 Bedroom 2 bath with space for classes and retreats

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

Secluded Montana Getaway w/ Fire Pit & Views!

3.0 star property
Ryegate
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

Autumn's Inn

Autumn's Inn

10/10 Excellent
"Good variety"
Gary 6-night trip
Posted 13 days ago
Autumn's Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Roundup in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $173 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

Small Town Big Sky: This vacation home rental outside of Roundup offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 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.