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Crook County Holiday Rentals

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Top Holiday Rentals Destinations in Crook County

Lake house at Prineville Reservoir

9.0 out of 10, Wonderful, (51)
"My sister and I spent 5-nights at this lovely house getting flowers and food together for a friend’s wedding. The space was perfect. The deck- an excellent way to unwind after working on wedding prep. The bed was super comfortable. A beautiful home with very responsive hosts. Thank you"
Lake house at Prineville Reservoir

Brasada Ranch Retreat w/ Hot Tub + Views Resort Access w/ Pools, Horseback Riding, Sports, and More Hat Rock Loop by Avantstay

3.0 star property
Brasada Ranch Retreat w/ Hot Tub + Views Resort Access w/ Pools, Horseback Riding, Sports, and More Hat Rock Loop by Avantstay

Crooked River Ranch Cabins

3.0 star property
9.6 out of 10, Exceptional, (178)
"Amazing area, enjoyed the stay, very quiet and homey! Wished I had time to stay longer, next time through I’ll stay longer! "
The price is NZ$184
includes taxes & fees
1 Oct - 2 Oct
Crooked River Ranch Cabins

Wall Street Suites

3.0 star property
9.8 out of 10, Exceptional, (272)
"This was a great place to stay "
Wall Street Suites

Canyon Rim at Eagle Crest

4.5 star property
9.2 out of 10, Wonderful, (20)
"Great place!"
Canyon Rim at Eagle Crest

Luxury in Bend, OR | Guestroom + Nature Experience

3.0 star property
9.0 out of 10, Wonderful, (35)
"Wonderful property, staff, and location!"
The price is NZ$310
includes taxes & fees
12 Oct - 13 Oct
Luxury in Bend, OR | Guestroom + Nature Experience

Updated Mount Bachelor Village 2-bedroom Condo, Enjoy Resort Amenities! with AC

2.0 star property
9.6 out of 10, Exceptional, (28)
"Bend is fun. Nice clean place close to everything "
The price is NZ$487
includes taxes & fees
26 Oct - 27 Oct
Updated Mount Bachelor Village 2-bedroom Condo, Enjoy Resort Amenities! with AC

Luxury in Bend, OR | Deluxe Queen close to Nature

9.2 out of 10, Wonderful, (9)
"Great property and location"
The price is NZ$324
includes taxes & fees
29 Sept - 30 Sept
Luxury in Bend, OR | Deluxe Queen close to Nature

Luxury in Bend, OR | Bunk Bed Room close to Nature

9.2 out of 10, Wonderful, (39)
"We had the best time and there is so much to do at the hotel. It’s located right on the river. Great food everywhere even if you want to just eat at the hotel. "
The price is NZ$339
includes taxes & fees
29 Sept - 30 Sept
Luxury in Bend, OR | Bunk Bed Room close to Nature

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

10.0 out of 10, Exceptional, (314)
"Wonderful cottage. 5 minute walk to downtown, had everything we needed, very comfortable. "
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

Cozy retreat near downtown, amphitheater, short walk to Deschutes river, has AC!

10.0 out of 10, Exceptional, (35)
"Really nice place! Clean and beautiful. Perfect getaway for a trip to see a concert in Bend. "
Cozy retreat near downtown, amphitheater, short walk to Deschutes river, has AC!

Cute, Quiet & Private Bungalow - Newly Remodeled

10.0 out of 10, Exceptional, (19)
"Wish we could have stayed longer. It was a perfect size/location for us, and the owners are amazing! Don’t hesitate to book this perfect space "
The price is NZ$345
includes taxes & fees
29 Sept - 30 Sept
Cute, Quiet & Private Bungalow - Newly Remodeled

Eagle Crest: Resort Amenities-Spa-9th Hole-Views!

9.8 out of 10, Exceptional, (31)
"Super nice place and convenient location for us! "
The price is NZ$636
includes taxes & fees
29 Sept - 30 Sept
Eagle Crest: Resort Amenities-Spa-9th Hole-Views!

Lodge Vibes in the City - Large Log Home

10.0 out of 10, Exceptional, (27)
"Great time"
Lodge Vibes in the City - Large Log Home

Bend River Retreat

4.0 star property
9.8 out of 10, Exceptional, (152)
"The views from this home were amazing and the location was great with lots of walking trails and accessibility to Bend activities. Host was quick to respond to all needs. Accommodations were good for our group of 4 couples. "
Bend River Retreat

Golden Escape- Private Hot tub, Dog Friendly

9.4 out of 10, Exceptional, (91)
"Great location. Quiet, with a terrific bunkroom.Room for parents, grandparents and kids!"
Golden Escape- Private Hot tub, Dog Friendly

The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

3.0 star property
10.0 out of 10, Exceptional, (2)
"The Quilty of the condo. Beds were very comfortable. "
The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

Fabulous Eagle Crest Resort Juniper Meadow, Private Hot Tub, Golf Course, Pool

10.0 out of 10, Exceptional, (134)
"Loved staying here! The owners were very accommodating and were available to answer any questions that I had. This corner unit was spacious, clean and the kitchen was well stocked. Great location and it was nice to have the hot tub. I’d like to come back in the summer! "
Fabulous Eagle Crest Resort Juniper Meadow, Private Hot Tub, Golf Course, Pool

Family friendly home w/private indoor pool and outdoor hot tub!

9.6 out of 10, Exceptional, (39)
"The perfect spot for a family gathering! The amenities are over the top ! We loved our stay "
Family friendly home w/private indoor pool and outdoor hot tub!

1 bedroom Suite with a view of Mt. Bachelor in welcoming Bend OR.

10.0 out of 10, Exceptional, (28)
"I loved the location, the indoor and outdoor amenities, and the prompt communication from the host regarding check-in. "
1 bedroom Suite with a view of Mt. Bachelor in welcoming Bend OR.
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 Crook County Hotel Reviews

Find out more about Crook County

Find out more about Crook County

Everything you need to know about Crook County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Crook County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Crook County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Crook County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Crook County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crook County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crook County holiday rentals we have selected for you start as low as NZ$184 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Crook County rentals

At Expedia, we put the best Crook County holiday 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 Crook County 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 Crook County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crook County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.