
Crook County Vacations & Trips from $418
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Your Crook County Vacation
Book a vacation package to Crook County and make planning your getaway quick and easy. With all the logistics organized before you depart, you can focus on enjoying every second in this lively destination. Not sure where to stay first? Prineville is one of the leading cities to visit during a trip to Crook County. Whether you plan to travel on a shoestring or want to splurge, Expedia are here to help you customize your next Crook County vacation.
The Latest Crook County Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Seventh Mountain Resort
Seventh Mountain
Price was $531, price is now $418 per person
$418
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Redmond (RDM)
7.4/10 Good! (426 reviews)
Everything was passable but shoddy. There was toilet paper, but the holder was detatched from the wall. The shower was fine, but there was no shower curtain. This type of thing. Pretty expensive for a mid experience.
Reviewed on Aug 4, 2025

Canyon Rim at Eagle Crest
Save 100% on your flight
Price was $725, price is now $481 per person
$481
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Redmond (RDM)
9.2/10 Wonderful! (16 reviews)
2 bedroom luxury condo with full kitchen, washer and dryer. Near sports center and bike rental.
Reviewed on Aug 11, 2025

Brasada Ranch
Save 100% on your flight
Price was $1,153, price is now $871 per person
$871
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Redmond (RDM)
9.4/10 Exceptional! (302 reviews)
comfortable beds, good amenities. Nice to have multiple eating places. Hot tub was lovely after a long day of hiking.
Reviewed on Aug 28, 2025

Ski Inn Taphouse Hotel
Price was $776, price is now $602 per person
$602
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Redmond (RDM)
9.6/10 Exceptional! (137 reviews)
This was one of the nicest hotels I've stayed at. Loved the giant wrap around deck at the heart of sisters and across the street from Sister's Bakery (which is delicious) and last but not least, that bathroom and shower were fantastic. Thank you guys so much!
Reviewed on Aug 18, 2025

WorldMark Eagle Crest
Price was $593, price is now $479 per person
$479
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Redmond (RDM)
8.4/10 Very Good! (112 reviews)
Eagle Crest is in a beautiful area and a great place to go all year. There are many activities including golf, tennis, swimming, a spa, etc. and many lovely walking trails. There are places to eat on site but it's a short drive to both Redmond and Sisters for good selections in restaurants.
Reviewed on Aug 16, 2025
Crook County Hotel Deals

High Desert Inn
123 NE 3rd Street, Prineville, OR
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $64 total per night from Sep 8 to Sep 9
$64 total
Sep 8 - Sep 9
Total with taxes and fees

Brasada Ranch
16986 Sw Brasada Ranch Rd, Powell Butte, OR
Fully refundableReserve now, pay when you stay
$330 nightly
The price is $363 total per night from Oct 1 to Oct 2
$363 total
Oct 1 - Oct 2
Total with taxes and fees
9.2/10 Wonderful! (300 reviews)
"comfortable beds, good amenities. Nice to have multiple eating places. Hot tub was lovely after a long day of hiking."
Reviewed on Aug 28, 2025

Country Inn & Suites by Radisson, Prineville, OR
1773 NE Third Street, Prineville, OR
Fully refundable
$143 nightly
The price is $157 total per night from Sep 7 to Sep 8
$157 total
Sep 7 - Sep 8
Total with taxes and fees
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.