Osage Holiday Rentals

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Holiday Rentals in Osage

Cozy cabin in the beautiful Black Hills

9.8 out of 10, Exceptional, (9)
"Everything was perfect—an isolated area away from everything else. The only trouble was that the address on Google Maps is about 2 miles off from the actual location. There is no cell reception in this area, and the house is located further West into Wyoming than what Google indicated. "
The price is AU$792
includes taxes & fees
11 Dec - 12 Dec
Cozy cabin in the beautiful Black Hills

Mountain getaway. Located on 7 acres at 6,500 foot elevation. Elk, deer, turkey.

9.8 out of 10, Exceptional, (59)
"Have everything you need here!"
Mountain getaway. Located on 7 acres at 6,500 foot elevation. Elk, deer, turkey.

Rustic log cabin in the beautiful Wyoming Black Hills!

9.6 out of 10, Exceptional, (117)
"Great cabin with beautiful 360 degree Wyoming views. Close to Devils Tower and not far from South Dakota black hills attractions. Would definitely recommend. "
Rustic log cabin in the beautiful Wyoming Black Hills!

Rustic Small Cabin in the Black Hills of Wy. Snowmobile right out the drive!

9.8 out of 10, Exceptional, (7)
"All was well. My only concern was the bathroom door (or the lack thereof). Everything was as listed and bottle of wine in the frig was a nice touch but we don't drink and left it for the next guest. We are glad we stayed and had a good time. We tried to leave the cabin in as good condition as when we arrived."
Rustic Small Cabin in the Black Hills of Wy. Snowmobile right out the drive!

Home on the Range

10.0 out of 10, Exceptional, (6)
"The cabin was a great place to stay. It is peaceful, lots of area to walk around outside and loved sitting outside in the evenings. The beds were very comfortable, good supply of towels, and the kitchen is adequately supplied with dishes,etc. We would definitely stay here again. "
Home on the Range

Kara Creek Ranch - King Bed Cabin with Kitchen #6

9.6 out of 10, Exceptional, (13)
"We really enjoyed our stay."
The price is AU$264
includes taxes & fees
30 Nov - 1 Dec
Kara Creek Ranch - King Bed Cabin with Kitchen #6

Kara Creek Ranch - 2 Bedroom Cabin with Kitchenette #3

9.4 out of 10, Exceptional, (16)
"Had a good time with good food and gracious hosts. "
The price is AU$281
includes taxes & fees
1 Dec - 2 Dec
Kara Creek Ranch - 2 Bedroom Cabin with Kitchenette #3

Kara Creek Ranch - Log Cabin

10.0 out of 10, Exceptional, (14)
"Amazing and iconic, just sit on the porch, no mosquitoes, and take in the view"
Kara Creek Ranch - Log Cabin

Krell’s Korral Tiny Cabin

9.6 out of 10, Exceptional, (18)
"Very nice"
The price is AU$244
includes taxes & fees
11 Dec - 12 Dec
Krell’s Korral Tiny Cabin

Kara Creek Queen Bed Cabin #9

9.6 out of 10, Exceptional, (12)
"Loved the property , staff was very nice , saloon was cool !"
The price is AU$203
includes taxes & fees
30 Nov - 1 Dec
Kara Creek Queen Bed Cabin #9

4bdr with a Beautiful Mountain View while relaxing in a Jacuzzi

9.0 out of 10, Wonderful, (7)
"The house was clean and very comfortable. It worked perfect for our family stay."
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, (11)
"Highlight of our cross-country trip. We ate dinner in the ranch house and my 3 teenage kids were in heaven. The saloon was so much fun with live music, singing, and playing pool. The ranch hand gave us a tour of the horse barn. Wish we had time for a trail ride but were just passing through. We also saw mule deer and wild turkeys as we walked around the area. The staff were all so friendly, we felt like we really belonged. We will be back for the full experience one day soon. Bunk house was...
Kara Creek Ranch - Rustic 2 Bedroom Cabin #5

Quiet Newcastle Apartment w/ Step-Free Access

10.0 out of 10, Exceptional, (2)
" Very easy checkin for a first timer. Place was very user friendly with no steps to walk over. All appliances were top notch and worked as supposed to. Seprate heat,air and water heater, no problem with sharing room tempeture. Owner was presennt occasianlly but was quiet and in seperate part of the house. If you enjoy wildlife this is place for you, bird feeders that brought in song birds, deer, turkeys and a passing through bobcat and coyote. I stayed 10-11 days and was thoroughly...
Quiet Newcastle Apartment w/ Step-Free Access

Kara Creek Ranch - King Bed Cabin #8

9.2 out of 10, Wonderful, (19)
"We were only here a day, but my kids and I had a great time! The property is beautiful and the service is spectacular! Loved the saloon and enjoyed home cooked breakfast and dinner! My daughter is terrified of horses but they eased her into meeting them and got her comfortable enough to try a trail ride. Kids asked to come back next year which is the ultimate stamp of approval!"
The price is AU$238
includes taxes & fees
30 Nov - 1 Dec
Kara Creek Ranch - King Bed Cabin #8

Trailshead Lodge Cabin 1

The price is AU$389
includes taxes & fees
2 Dec - 3 Dec
Trailshead Lodge Cabin 1

Kara Creek Ranch - Double Bed Cabin with Kitchen #7

10.0 out of 10, Exceptional, (3)
"thank you"
The price is AU$264
includes taxes & fees
30 Nov - 1 Dec
Kara Creek Ranch - Double Bed Cabin with Kitchen #7

Quiet Newcastle Apartment w/ Step-free Access

3.0 star property
Quiet Newcastle Apartment w/ Step-free Access

Trailshead Lodge - Cabin 3

The price is AU$389
includes taxes & fees
2 Dec - 3 Dec
Trailshead Lodge - Cabin 3

Kara Creek Ranch - 3 Bed Cabin #1

8.0 out of 10, Very good, (3)
"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...
Kara Creek Ranch - 3 Bed Cabin #1

Kara Creek Ranch - 2 bed cabin

10.0 out of 10, Exceptional, (1)
"Devin, Jordan, and the rest of the crew were amazing as always!!! Love this place."
The price is AU$281
includes taxes & fees
1 Dec - 2 Dec
Kara Creek Ranch - 2 bed cabin
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 Osage you may be interested in

Serena Inn & Suites - Sundance

2.5 star property
8.4 out of 10, Very good, (880)
"Clean hotel, reasonably priced and basic breakfast."
The price is AU$155
includes taxes & fees
30 Nov - 1 Dec
Serena Inn & Suites - Sundance

Newcastle Lodge and Convention Center

3.5 star property
9.0 out of 10, Wonderful, (446)
"Great stay, great place!"
The price is AU$188
includes taxes & fees
30 Nov - 1 Dec
Newcastle Lodge and Convention Center

Arrowhead Motel

2.0 star property
9.0 out of 10, Wonderful, (762)
"It was okay for the size of that facility; the room was small, and we stayed there only one night and we were satisfied."
The price is AU$130
includes taxes & fees
1 Dec - 2 Dec
Arrowhead 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

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.