Photo by Casey A. Pierson

Crook County Holiday Rentals

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Top Holiday Rentals Destinations in Crook County

Brasada Ranch High Desert Luxury Cabin

10.0 out of 10, Exceptional, (31)
"The house was fantastic. Perfect size for 2 couples. Clean and well stocked. House had everything we needed. Also like the fact that the restaurant was close by."
Brasada Ranch High Desert Luxury Cabin

Crooked River Ranch Cabins

3.0 star property
9.8 out of 10, Exceptional, (106)
"Meagan was great!!! Loved the space & wildlife!!"
The price is AU$154
includes taxes & fees
2 Dec - 3 Dec
Crooked River Ranch Cabins

Wall Street Suites

3.0 star property
9.8 out of 10, Exceptional, (229)
"Great stay and I would stay here again! "
The price is AU$282
includes taxes & fees
1 Dec - 2 Dec
Wall Street Suites

"Leaf Your Troubles Behind"-Ground level condo near downtown Bend

9.0 out of 10, Wonderful, (23)
"I used this space a temporary home while in Bend and working remotely. The condo was exactly what I needed for myself, and then for my husband when he joined me later in the week. For those that are sensitive to sounds, be aware that this is a ground floor unit. While it was bothersome at times for me because it did get to be overly "obnoxious" from time to time, overall I was okay with the fact that you could hear the tenants' upstairs movements because that's just part of the "condo style"...
"Leaf Your Troubles Behind"-Ground level condo near downtown Bend

"Slopey Seconds" Riverfront condo with balcony near downtown Bend

9.6 out of 10, Exceptional, (42)
"Perfect condo for our stay in Bend! Short walk to downtown and lovely river sounds!"
The price is AU$315
includes taxes & fees
1 Dec - 2 Dec
"Slopey Seconds" Riverfront condo with balcony near downtown Bend

West Side, Walk to Newport and Downtown, Bocce Ball Court

9.6 out of 10, Exceptional, (52)
"We need the house for a work trip. House was clean. It was a short job to the river house for the conference."
West Side, Walk to Newport and Downtown, Bocce Ball Court

Hot Tub, Updated, Outdoor Spaces, Steps to Old Mill and River

9.4 out of 10, Exceptional, (105)
"We just loved basing ourselves here while we were in Bend. Very well appointed and decorated. Loved having the garage and hot tub. Plenty of space for grandparents, parents and granddaughter and we all had our own bathrooms!"
Hot Tub, Updated, Outdoor Spaces, Steps to Old Mill and River

Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

9.6 out of 10, Exceptional, (71)
"I rented this little home because my daughter had surgery in Bend and I live in Texas. I came to help nurse her back to health after the surgery. She ended up co"
Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

"Mount Your Blessings"-Upscale condo on edge of downtown

9.4 out of 10, Exceptional, (34)
"Was in town for business. Perfect location and close to everything that I needed "
"Mount Your Blessings"-Upscale condo on edge of downtown

LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.

9.6 out of 10, Exceptional, (18)
"Loved my week here with my pup. House was cozy & centrally located. For the most part, less than 7 minutes driving to anywhere I needed to go within the city limits. House was well-stocked, from the towels to blankets to kitchen utensils to laundry room detergent etc. I don’t normally write about kitchen appliances and utensils, but this was the best-stocked setup I’ve ever seen. I cook a lot, so I notice these things. Was impressed! I’d definitely came back and stay here again. "
LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.

"Riverrun Retreat" Cottage along the Deschutes River, near Downtown Bend

9.6 out of 10, Exceptional, (21)
"A lovely few days visiting friends "
"Riverrun Retreat" Cottage along the Deschutes River, near Downtown Bend

"Slope Floats" Downtown Riverfront Condo. Best location in Bend!

9.4 out of 10, Exceptional, (60)
"We walked to almost everything in town from here and the view is fantastic!"
"Slope Floats" Downtown Riverfront Condo. Best location in Bend!

Hot Tub, AC, Beautiful, Fully Fenced Yard, Close to Everything!

9.6 out of 10, Exceptional, (33)
"Its in a very nice neighborhood with some friendly people I see outside in front. The house is perfect for what I'm looking for with pet. I will come again with pet as I didn't at first. "
Hot Tub, AC, Beautiful, Fully Fenced Yard, Close to Everything!

Hot tub, Steps to Old Mill, Close to Downtown, Fireplace, AC, Pet Friendly

9.6 out of 10, Exceptional, (79)
"The townhouse was very clean and had everything we needed for our stay. We loved the layout and that each bedroom had an ensuite bathroom. We enjoyed using the hot tub.We had our 2 dogs with us and having a fenced in backyard was wonderful for traveling with dogs. The location was fantastic. Everything we did was never more than 15 minutes away. We would definitely stay here again."
Hot tub, Steps to Old Mill, Close to Downtown, Fireplace, AC, Pet Friendly

Hot Tub, Gorgeous, Updated, Westside Trail, Explore Bend

9.6 out of 10, Exceptional, (20)
"We had an excellent time at this property! I wish we would’ve know that there were strict quiet hours starting at 9pm compared to the city mandate of 10pm as this was an issue one night while we were outside until 9:30pm. There was quick communication with the property host and all was clarified easily and respectfully. Would recommend for anyone as long as you are ok with the quiet hours! "
Hot Tub, Gorgeous, Updated, Westside Trail, Explore Bend

Perfect Bend Bungalow, Fireplace, A/C, Walk to Everything!

9.4 out of 10, Exceptional, (87)
"This house was perfect for our 2 day stay in Bend. Had everything we needed. Walking distance to everything Bend has to offer."
Perfect Bend Bungalow, Fireplace, A/C, Walk to Everything!

A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage

9.6 out of 10, Exceptional, (100)
"Great place close to restaurants and breweries. Short drive biking. "
A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage

"Cabin Leisure" Riverfront cottage just steps from Deschutes River

9.6 out of 10, Exceptional, (45)
"Perfect getaway for our anniversary; everything was perfect and just as advertised. "
"Cabin Leisure" Riverfront cottage just steps from Deschutes River

"Otter Sight" Riverside Cottage - Just Steps from the Deschutes

9.4 out of 10, Exceptional, (36)
"This property was in an amazing location, close to downtown and shopping. The view of the river couldn’t be beat. Only complaint, the bed was rough . Felt like we were sleeping on a straight box spring, no mattress. Otherwise great rental, and responsive hosts. "
"Otter Sight" Riverside Cottage - Just Steps from the Deschutes

Gorgeous! Fenced Yard, AC, Convenient Location

9.8 out of 10, Exceptional, (19)
"Loved it! We were very excited when we found out the property was available for our family gathering again this year. Everything was very clean and it’s in a great area. Hoping to stay here again next year!!! "
Gorgeous! Fenced Yard, AC, Convenient Location
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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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.