Photo by Casey A. Pierson

Holiday Rentals in Crook County

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Featured Holiday Rentals in Crook County

Crooked River Ranch Cabins

3.0 star property
9.8 out of 10, Exceptional, (110)
"Excellent Place to stay for a Getaway "
The price is €106
includes taxes & fees
19 Feb - 20 Feb
Crooked River Ranch Cabins

Extraordinary Riverfront Home Next to Biking, Hiking & Fishing

4.0 star property
9.8 out of 10, Exceptional, (140)
"The owner was most helpful in sorting a few small problems. Some of the bathrooms were slow to drain."
Extraordinary Riverfront Home Next to Biking, Hiking & Fishing

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

9.4 out of 10, Exceptional, (3)
"This place was outstanding for the price. Room was clean, amenities were perfect, and location was beautiful."
The price is €109
includes taxes & fees
19 Feb - 20 Feb
Luxury in Bend, OR | Bunk Bed Room close to Nature

Wall Street Suites

3.0 star property
9.8 out of 10, Exceptional, (236)
"We love staying at the Wall Street Suites. The rooms have a lot of amenities and the location is fantastic. Everyone who works there is super communicative and they welcomed our dog with open arms. Highly recommend, great value. "
The price is €192
includes taxes & fees
27 Feb - 28 Feb
Wall Street Suites

Walk To Downtown & The Last Blockbuster from recently renovated home

9.6 out of 10, Exceptional, (42)
"I travelled from Seattle to meet my college aged daughter and 2 of her friends from the University of Oregon in Bend for a long weekend. The house was perfect for the 4 of us and could easily have accommodated 2 more people. The mattresses on the beds were very comfortable. The kitchen was well stocked. The washer and dryer and all other appliances worked well. The bathrooms were small and the showers a bit outdated but everything worked just fine. We were able to drive into downtown Bend for...
The price is €296
includes taxes & fees
23 Feb - 24 Feb
Walk To Downtown & The Last Blockbuster from recently renovated home

Fantastic Eagle Crest Home! Resort Pool, Fitness Center, Golf, Pickleball. Fireplace. Quiet Street.

9.6 out of 10, Exceptional, (20)
"This trip, we needed a house for co-workers on a week-long business trip. The house was spacious, well-appointed, and conveniently located for us. There were enough bathrooms for everyone and plenty of personal space. Our admin person even had a small office for the bulk of her work. The walking trails were great for morning runs too! Looking forward to coming back with another group or our kids for a vacation!"
Fantastic Eagle Crest Home! Resort Pool, Fitness Center, Golf, Pickleball. Fireplace. Quiet Street.

Hot Tub, Amazing Walkable Location, Views, Fenced Backyard

9.6 out of 10, Exceptional, (74)
"The house was nicely updated with lots of warmth. The area was really quiet despite it's proximity to Reed Markt, a local arterial Rd with direct access to Mt Bachelor, Deschutes River and High Lakes. You can walk form the private path nearby into the Old Mill. Loved having the hot tub after a day of snowboarding and my teen girls felt safe. Staff was very attentive and kind. Overall a great stay. "
Hot Tub, Amazing Walkable Location, Views, Fenced Backyard

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

9.2 out of 10, Wonderful, (29)
"Always a great affordable place to stay. "
The price is €262
includes taxes & fees
8 Mar - 9 Mar
"Leaf Your Troubles Behind"-Ground level condo near downtown Bend

Perfect Retreat Luxury Home, Guest Quarters, A/C, Foosball, Ping Pong

9.6 out of 10, Exceptional, (92)
"Nice place, great location "
Perfect Retreat Luxury Home, Guest Quarters, A/C, Foosball, Ping Pong

SW Chamberlain Street | Southern Crossing | hot tub pet friendly (dog)

9.6 out of 10, Exceptional, (28)
"This home worked out great for our group of five adults and an infant. The house was cozy, had everything we needed, and was an awesome location where we could walk to the Old Mill District. We would definitely stay here again!"
SW Chamberlain Street | Southern Crossing | hot tub pet friendly (dog)

The Aerie Suites by AvantStay

3.0 star property
The Aerie Suites by AvantStay

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

2.0 star property
9.6 out of 10, Exceptional, (8)
"Great spot. Thanks!"
The price is €246
includes taxes & fees
19 Feb - 20 Feb
Updated Mount Bachelor Village 2-bedroom Condo, Enjoy Resort Amenities! with AC

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

9.8 out of 10, Exceptional, (22)
"My friends and I visited for a long weekend and were so impressed with both the property and the property manager! The house was gorgeous, clean and stocked with everything we needed. The manager made sure to check in with us about anything that we needed and was extremely quick with communication. We will definitely be back sometime!"
Hot Tub, Gorgeous, Updated, Westside Trail, Explore Bend

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

9.4 out of 10, Exceptional, (39)
"Perfect location easy to walk to everything, room was clean and comfortable!"
"Otter Sight" Riverside Cottage - Just Steps from the Deschutes

Stay Steps from the Deschutes River & Drake Park, Old Bend's charm awaits you.

10.0 out of 10, Exceptional, (77)
"Cutest bungalow ever! Clean and well maintained. The location is awesome close to river trail and Old Mill district. We’ll be back for sure. "
Stay Steps from the Deschutes River & Drake Park, Old Bend's charm awaits you.

6BR | 5 King Beds | EV | 10min Downtown

10.0 out of 10, Exceptional, (3)
"The house was clean and very welcoming. There were 12 of us all together and plenty of room. The beds were comfortable. The bathrooms had plenty of fluffy white towels and if each one of us wanted to cuddle up with a throw blanket there were enough. The theater room was a big bonus the teenage boys enjoyed. The canals on either side of the house are seasonal and are dry in the winter. I would absolutely stay here again. "
6BR | 5 King Beds | EV | 10min Downtown

Ultimate River House-20 mins to Bachelor. Old Mill, Restaurants, Fireplace, Heated Deck

10.0 out of 10, Exceptional, (69)
"This is a house rental you will want to rent again. House is big and has all the amenities and is located close to everything. "
Ultimate River House-20 mins to Bachelor. Old Mill, Restaurants, Fireplace, Heated Deck

Elegant & Spacious, 3 Master King Suites! Community Hot Tub (and Seasonal Pool)

9.8 out of 10, Exceptional, (64)
"This was our third time renting this property. Very nice home. Well appointed. Just needs an ice cream scooper. We enjoyed the nearby river walk and skiing on Mt Bachelor this year. It snowed during our entire time. We loved it!"
Elegant & Spacious, 3 Master King Suites! Community Hot Tub (and Seasonal Pool)

Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park

9.8 out of 10, Exceptional, (120)
"The place was very clean. Great location. Only issue was when the was services at the church across the street people blocked the drive that we were supposed to use. Had to park in the covered drive"
Convenient & Cozy Cottage On Newport Near River, Downtown & Drake Park

Pool Table, Gourmet Kitchen, Outdoor Living

9.6 out of 10, Exceptional, (71)
"Host was very accommodating "
Pool Table, Gourmet Kitchen, Outdoor Living
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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