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, (106)
"It was a wonderful time. Everything was great. The only negative aspect was that the shower was so cramped. Other than that, it was a very good stay. Would come back again."
The price is NZ$171
includes taxes & fees
1 Dec - 2 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 NZ$314
includes taxes & fees
26 Nov - 27 Nov
Wall Street Suites

Walk To Downtown & The Last Blockbuster from recently renovated home

9.6 out of 10, Exceptional, (35)
"5 adults stayed at the house 10/11. We were attending the Bend fall festival and didnt want to have to drive home after. Convenient/clean, good communication with owner."
The price is NZ$533
includes taxes & fees
2 Dec - 3 Dec
Walk To Downtown & The Last Blockbuster from recently renovated home

"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

Private Hot Tub & Deck, Family, Eagle Crest, Sunny Getaway!

9.4 out of 10, Exceptional, (26)
"Nice house, very clean, easy to communicate with host. Very comfortable, convenient location. "
Private Hot Tub & Deck, Family, Eagle Crest, Sunny Getaway!

"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 NZ$348
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!

Great Location, Fenced Yard, A/C, Light & Bright

9.6 out of 10, Exceptional, (45)
"We rented this property for our adult kids and adult grandkids while celebrating our 50th Anniversary. The management staff was excellent, but the owner changed the sleeping availability from 8 adults to 6 without notifying us. Luckily 2 of the 8 were young adults and able to make a couple of roll away beds work. All in all the property was very clean and everyone was happy:)"
Great Location, Fenced Yard, A/C, Light & Bright

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
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, (1013)
"Clean and quiet "
The price is NZ$191
includes taxes & fees
8 Dec - 9 Dec
Country Inn & Suites by Radisson, Prineville, OR

Best Western Prineville Inn

2.5 star property
8.6 out of 10, Excellent, (778)
"The staff was very kind . "
The price is NZ$213
includes taxes & fees
26 Nov - 27 Nov
Best Western Prineville Inn

Econo Lodge

2.0 star property
6.8 out of 10, (377)
"Nice and inexpensive "
The price is NZ$116
includes taxes & fees
10 Dec - 11 Dec
Econo 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.
Beautiful view of the beach with palm trees

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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.

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 9 Expedia holiday rentals in Prineville for a memorable holiday.

What can I see and do in Prineville?

Ochoco Creek 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 Prineville Reservoir 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.