Osage Holiday Rentals

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Holiday Rentals in Osage

Rustic log cabin in the beautiful Wyoming Black Hills!
9.6 out of 10, Exceptional, 107 reviews
"Serenity and the area is so very beautiful. I would love to live there as the town of Sundance very friendly and clean. Jay checked on us twice to make sure everything was going okay. Thank you Jay for your hospitality! "
Rustic log cabin in the beautiful Wyoming Black Hills!
Rustic Small Cabin in the Black Hills of Wy. Snowmobile right out the drive!
9.6 out of 10, Exceptional, 5 reviews
"It was a perfect location, wonder scenery...would love to visit there again."
Rustic Small Cabin in the Black Hills of Wy. Snowmobile right out the drive!
Mountain getaway. Located on 7 acres at 6,500 foot elevation. Elk, deer, turkey.
9.8 out of 10, Exceptional, 56 reviews
"Greg was great to work with and his communication amazing (especially as we got close to trip date and snow was questionable)! Our Christmas wish for snow came true and we had a great time! Thank you, Greg!"
Mountain getaway. Located on 7 acres at 6,500 foot elevation. Elk, deer, turkey.
Kara Creek Ranch - 2 bed cabin
10.0 out of 10, Exceptional, 1 review
"Devin, Jordan, and the rest of the crew were amazing as always!!! Love this place."
The price is NZ$294
per night
18 Jul - 19 Jul
Kara Creek Ranch - 2 bed cabin
Cozy cabin in the beautiful Black Hills
9.6 out of 10, Exceptional, 5 reviews
"Great place to stay"
The price is NZ$829
per night
27 Jun - 28 Jun
Cozy cabin in the beautiful Black Hills
Historic Stay Inn.
10.0 out of 10, Exceptional, 14 reviews
"Recommended to anybody"
Historic Stay Inn.
Home on the Range
10.0 out of 10, Exceptional, 3 reviews
"My wife and I have a very busy life and she is very social. We have eight children. Five of our children are off living their lives outside of our home and we are left with 9-year-old triplets and our 3 and 1/2-year-old German Shepherd to which my wife and I, the triplets and our German Shepherd Diesel was allowed to stay here. There was no TV. There was plenty of games, there was the most amazing scenery, we did not have the best cell phone service which made it even better, our big kids have...
Home on the Range
Kara Creek Ranch - King Bed Cabin with Kitchen (#6)
10.0 out of 10, Exceptional, 12 reviews
"We really enjoyed our stay."
The price is NZ$276
per night
18 Jul - 19 Jul
Kara Creek Ranch - King Bed Cabin with Kitchen (#6)
Kara Creek Ranch - 2 Bedroom Cabin with Kitchenette (#3)
9.4 out of 10, Exceptional, 13 reviews
"If you are looking for a relaxing and quiet place to get away this is pretty good. There is quite a drive to get in, but it is stunning. Free range cattle, horses, deer are visible. I stayed in unit 3. It was clean but felt a little old - no big deal. When I arrived, I was not sent a code but the neighbor told me it was unlocked. The saloon was a hoot. Live music and great conversation with Montie (former World Champion Rodeo personality). They had breakfast at 8:00 am, I did not...
The price is NZ$294
per night
18 Jul - 19 Jul
Kara Creek Ranch - 2 Bedroom Cabin with Kitchenette (#3)
Kara Creek Ranch - Log Cabin
10.0 out of 10, Exceptional, 12 reviews
"Quiet cabin in rural Wyoming. We loved sitting in swing and enjoying time relaxing as a family."
The price is NZ$447
per night
19 Jul - 20 Jul
Kara Creek Ranch - Log Cabin
Krell’s Korral Tiny Cabin
9.6 out of 10, Exceptional, 16 reviews
"Bev made us feel at home during our stay. Everything was as advertised and we plan to stay there again in the future."
The price is NZ$255
per night
27 Jun - 28 Jun
Krell’s Korral Tiny Cabin
Kara Creek Queen Bed Cabin (#9)
9.4 out of 10, Exceptional, 8 reviews
"Not the biggest, just the Best working Cattle Ranch with cabins.Picked it for our 25th. Wife is a Big horse Lover. They did not need our help in July or August. Special thanks to some of the staff, Chris the trail boss Ladina the Superb cook, and the Bull-Horned hood ornament of the place. Cowboy Hawkeye Henson. For his stories and entertainment. Thanks to all ..."
The price is NZ$212
per night
18 Jul - 19 Jul
Kara Creek Queen Bed Cabin (#9)
4bdr with a Beautiful Mountain View while relaxing in a Jacuzzi
9.2 out of 10, Wonderful, 5 reviews
"Paul was a great host. Everything was clean."
4bdr with a Beautiful Mountain View while relaxing in a Jacuzzi
Kara Creek Ranch - Rustic 2 Bedroom Cabin (#5)
10.0 out of 10, Exceptional, 8 reviews
"First time we’ve ever stayed at a working ranch and it was awesome! The cabins are rustic and simple and exactly what you need for a good nights sleep. Our 2 year old had a great time dancing around the saloon and listening to live music played by Monty, a former rodeo champion! Everyone was so wonderful and welcoming. When we arrived we met the owner and he was such a pleasure to talk to. The next morning all of the renters went to the ranch house for a delicious breakfast together. Highly...
The price is NZ$294
per night
18 Jul - 19 Jul
Kara Creek Ranch - Rustic 2 Bedroom Cabin (#5)
Quiet Newcastle Apartment w/ Step-Free Access
10.0 out of 10, Exceptional, 1 review
"Very clean, quiet, private. Contact person accommodating and kind. Will definitely stay here again if in the area and would highly recommend to others!"
Quiet Newcastle Apartment w/ Step-Free Access
Kara Creek Ranch - King Bed Cabin (#8)
9.4 out of 10, Exceptional, 17 reviews
"The property is absolutely stunning! We picked up dinner before heading into the ranch as it is about 20 mins off the highway and closest town. Highly recommend getting up early to watch the sunrise come over the mountains! Beautiful!"
The price is NZ$248
per night
4 Jul - 5 Jul
Kara Creek Ranch - King Bed Cabin (#8)
Kara Creek Ranch - Double Bed Cabin with Kitchen (#7)
10.0 out of 10, Exceptional, 3 reviews
"thank you"
The price is NZ$276
per night
8 Jul - 9 Jul
Kara Creek Ranch - Double Bed Cabin with Kitchen (#7)
Quiet Newcastle Apartment w/ Step-free Access
3.5 star property
Quiet Newcastle Apartment w/ Step-free Access
Kara Creek Ranch - 3 Bed Cabin (#1)
8.0 out of 10, Very good, 3 reviews
"If you like rustic and simple, the peacefulness of the country and being "off the grid" you are gonna Love this place! Enjoy the thrill as you drive down the miles of winding gravel roads wondering if the next bend is your destination. And finally you are there... feel the peace as you slowly roll down the drive... no traffic, no noise, no hassle. Just good country folks respecting your space, but there for you if you need something. Coming here was the best part of our trip. Thank you Cassie...
The price is NZ$230
per night
4 Jul - 5 Jul
Kara Creek Ranch - 3 Bed Cabin (#1)
Kara Creek - Queen Bed Cabin (#2)
9.0 out of 10, Wonderful, 2 reviews
"People were great and friendly, the provided breakfast was yummy, hiking in the valley was peaceful and plenty of places to explore. My only issue was that the AC didn’t work the fan couldn’t keep up w 90 degree heat - too hit."
Kara Creek - Queen Bed Cabin (#2)
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See all available properties in Osage
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.

Other types of properties in Osage you may be interested in

Serena Inn & Suites - Sundance
2.5 star property
8.6 out of 10, Excellent, 747 reviews
"The lady at check in was very pleasant. The lovby looked clean. The dining area was clean. We wrnt to our room, which was also very clean. We made use of the refrigerator since we were just passing thru the area. Both the fridge and freezer worked great. Microwave also worked. Bathroom was clean. Had the breakfast the next morning. There was juice, coffee, yogurt, bagels, muffins, bread, biscuits & gravy, cereal and hard boiled eggs. Only thing missing was fresh fruit. Wed...
The price is NZ$256
per night
22 Jun - 23 Jun
Serena Inn & Suites - Sundance
Arrowhead Motel
2.0 star property
9.0 out of 10, Wonderful, 689 reviews
"Very welcoming and friendly proprietors, but not intrusive. The room was well furnished and comfortable. The towel folding is unmatched. Our stay was a charming experience. "
The price is NZ$156
per night
26 Jun - 27 Jun
Arrowhead Motel
Bear Lodge Motel
2.0 star property
8.0 out of 10, Very good, 471 reviews
"Had to change our room nut nonoroblem"
The price is NZ$164
per night
23 Jun - 24 Jun
Bear Lodge 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osage holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osage. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Osage. Seeing all the best attractions is bound to make you fall in love with Osage. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Osage short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Osage?

Yes, there are holiday rentals close to the most popular sights in Osage, or you can select a more secluded option if you're looking for a relaxing stay.

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

Mountain getaway. Located on 7 acres at 6,500 foot elevation. Elk, deer, turkey.: This holiday home rental outside of Osage is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Osage?

While exploring the area, visit the sights like Upton Old Town, Red Onion Museum and Cedar Pines Golf Course.

What’s a holiday rental in Osage like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osage. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.

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