Roundup Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Roundup

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

Apartment in 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
Interior
Quiet Country Burnt Cross Cabin close to Billings

Cabin in 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
House (1 Bedroom) | Interior
Near Hunting: Cozy Cabin w/ Deck in Grass Range!

Cottage in Grass Range

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

Cabin in Shepherd

10.0 out of 10, Exceptional, (3)
"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!"
United States
Jasmine D.
See the stars from this cozy guest cabin 30 minutes from Billings.
Fridge, microwave, oven, stovetop
Small Town Big Sky

Vacation Home in 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
Fridge, microwave, oven, stovetop
Tiny House in the country, close to Billings

Apartment in Worden

9.6 out of 10, Exceptional, (5)
"Had a fantastic stay! The bed was extremely comfortable and the little house is extremely adorable. "
United States
Kelsey
Tiny House in the country, close to Billings
Exterior
Restored Vintage Mobile Home on our small Private Ranch

Mobile Home in Lavina

9.0 out of 10, Wonderful, (8)
"Our stay was awesome!! 2nd time staying here and will definitely stay here again. "
United States
Kevin J.
The price is ￥12,462
￥26,917 total
includes taxes & fees
Dec 4 - Dec 5
Restored Vintage Mobile Home on our small Private Ranch
Exterior detail
Charming bungalow with AC and WiFi in a private rural part of Billings.

Vacation Home in 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

Vacation Home in Shepherd

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

Cottage in Ryegate

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

Small Town Big Sky

Small Town Big Sky

10/10 Excellent
"Have stayed here twice highly recommend if you can find it available always booked and for good reason. Great place "
Eric R. 3-night trip
Posted 1 month ago
Small Town Big Sky

Find out more about Roundup

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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.