Prineville Holiday Rentals

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Holiday Rentals in Prineville

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 AU$174
includes taxes & fees
22 Feb - 23 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."
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 AU$315
includes taxes & fees
23 Feb - 24 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 The bathrooms were small and the showers a bit outdated but everything worked just fine.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 AU$491
includes taxes & fees
24 Feb - 25 Feb
Walk To Downtown & The Last Blockbuster from recently renovated home

Bluebird Day - Ogden Getaway

10.0 out of 10, Exceptional, (7)
"Cute place it was exactly what we were looking for. Bed was very warm and everything was really clean. Will definitely be saving your listing for future visits. "
The price is AU$369
includes taxes & fees
24 Feb - 25 Feb
Bluebird Day - Ogden Getaway

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

West side dog-friendly cozy studio w/ private yard

10.0 out of 10, Exceptional, (8)
"Yard was so nice for my dogs to play around in! Hosts were kind and timely with any questions I had(they even baked us welcome cookies)! Check in was super easy with easy instructions! "
The price is AU$300
includes taxes & fees
4 Mar - 5 Mar
West side dog-friendly cozy studio w/ private yard

"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 AU$400
includes taxes & fees
8 Mar - 9 Mar
"Leaf Your Troubles Behind"-Ground level condo near downtown Bend

Cozy apartment in wonderful Bend with WiFi, AC

2.0 star property
Cozy apartment in wonderful Bend with WiFi, AC

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)

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 AU$403
includes taxes & fees
24 Feb - 25 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

Bluebird Day - Star Cottage

9.8 out of 10, Exceptional, (40)
"The house is very cute, cozy and clean. The fully fenced backyard was great for our dogs and also very clean. Kitchen was well appointed and beds were very comfortable. Would stay here again!"
Bluebird Day - Star Cottage

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
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 Prineville you may be interested in

Country Inn & Suites by Radisson, Prineville, OR

2.5 star property
9.2 out of 10, Wonderful, (1002)
"It was great."
The price is AU$178
includes taxes & fees
23 Mar - 24 Mar
Country Inn & Suites by Radisson, Prineville, OR

Best Western Prineville Inn

2.5 star property
8.6 out of 10, Excellent, (787)
"Always super easy check in, and the rooms are always clean. "
The price is AU$184
includes taxes & fees
23 Feb - 24 Feb
Best Western Prineville Inn

Riverhouse Lodge

3.5 star property
8.8 out of 10, Excellent, (1211)
"Great vibe, rooms have good options for families, we got the double queens with twin bunk beds over each, perfect option for those with kids. Location is right on river. Bar and lounge on site for a nice drink. Definitely would go back."
The price is AU$167
includes taxes & fees
7 Mar - 8 Mar
Riverhouse Lodge
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.

Frequently asked questions

Can I find holiday rentals in Prineville?

Yes, there are holiday rentals close to the most popular sights in Prineville, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Prineville has a good selection of restaurants. Make sure you have time to check out the riverfront and festivals during your trip.

What are some of the best holiday rentals that Prineville has to offer?

Perfect Retreat Luxury Home, Guest Quarters, A/C, Foosball, Ping Pong: This holiday home rental outside of Prineville is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 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.

How many holiday rentals are there in Prineville?

Choose from 8 Expedia holiday rentals in Prineville for a memorable holiday.

What can I see and do in Prineville?

Prineville Reservoir State Park and Crooked River are a couple of scenic spots to enjoy the outdoors, whereas A.R. Bowman Museum is one of the cultural attractions. Other places in town to visit include Ochoco Wayside State Park and Ochoco National Forest.

What are holiday rentals like in Prineville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Prineville. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.