Prineville Holiday Rentals

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Holiday Rentals in Prineville

Studio Suite
Crooked River Ranch Cabins
3.0 star property
9.8 out of 10, Exceptional, (52)
"This place was awesome! We plan on coming back soon!"
The price is NZ$219
includes taxes & fees
9 Jun - 10 Jun
Crooked River Ranch Cabins
Full-sized fridge, microwave, oven, stovetop
Wall Street Suites
3.0 star property
9.8 out of 10, Exceptional, (205)
"We appreciated the large kitchen and proximity of parking to our door. No long walk down a dark hall. Great location close to downtown and the river. Would have been great if the heat was on in the room prior to check in (it was close to freezing and took a bit to warm up). Appreciated the pup friendly items and the coffee/tea/cocoa in the kitchen. "
The price is NZ$522
includes taxes & fees
30 May - 31 May
Wall Street Suites
Exterior
"Slopey Seconds" Riverfront condo with balcony near downtown Bend
9.8 out of 10, Exceptional, (31)
"My dog and I stayed for two nights and it was great. The condo is right next to the river and a trail that goes along the river. Pioneer park is also about a block away and was great for quick potty walks for my dog. Close to downtown and all the shops and restaurants."
The price is NZ$353
includes taxes & fees
30 May - 31 May
"Slopey Seconds" Riverfront condo with balcony near downtown Bend
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Property grounds
Riverside condo with balcony - near parks, breweries, shops, & dining
9.6 out of 10, Exceptional, (44)
"Close to downtown and River walk"
The price is NZ$428
includes taxes & fees
3 Jun - 4 Jun
Riverside condo with balcony - near parks, breweries, shops, & dining
Fridge, microwave, oven, stovetop
Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown
9.6 out of 10, Exceptional, (64)
"Great cozy weekend getaway with your partner! 8mins from downtown and close to everything. Nice quiet, safe neighborhood. Definitely recommend (:"
Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown
Fridge, microwave, oven, stovetop
Gorgeous! Fenced Yard, AC, Convenient Location
10.0 out of 10, Exceptional, (9)
"This property is lovely and exactly as pictured. The place is very homey with comfortable beds and so many board games. My niece really enjoyed Operation. Communication with the property was immediate and super friendly. I would definitely stay again."
Gorgeous! Fenced Yard, AC, Convenient Location
Exterior
Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks
9.4 out of 10, Exceptional, (17)
"We had a great weekend stay at this property. The check-in and check-out processes were flawless. The neighborhood was quit and it’s close to downtown. The home is super clean and the kitchen is well stocked. Perfect for a quick weekend getaway!"
Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks
Aerial view
"Slope Floats" Downtown Riverfront Condo. Best location in Bend!
9.6 out of 10, Exceptional, (45)
"Nice river view. Good central location for our hikes and exploring. Plenty of space for the two of us. Enjoyed being by the Riverwalk. Lots of good light in the condo"
The price is NZ$335
includes taxes & fees
29 May - 30 May
"Slope Floats" Downtown Riverfront Condo. Best location in Bend!
Property grounds
West Side, Walk to Newport and Downtown, Bocce Ball Court
9.6 out of 10, Exceptional, (47)
"Well stocked kitchen!!"
West Side, Walk to Newport and Downtown, Bocce Ball Court
Pool
"Leaf Your Troubles Behind"-Ground level condo near downtown Bend
9.2 out of 10, Wonderful, (13)
"We thoroughly enjoyed our stay at this propoerty. It was exactly as advertised and was very convenient to everywhere. We would definitley stay there again when we visit our family in Bend!"
The price is NZ$406
includes taxes & fees
13 Jun - 14 Jun
"Leaf Your Troubles Behind"-Ground level condo near downtown Bend
Fridge, microwave, oven, stovetop
Galveston Corridor! Backyard w Firepit. Dog Friendly. Workstation. Steps to Dining, Brews, Coffee
9.4 out of 10, Exceptional, (10)
"House is great and location is even better. Everything was clean and check in was easy. Would stay here again."
Galveston Corridor! Backyard w Firepit. Dog Friendly. Workstation. Steps to Dining, Brews, Coffee
Fridge, microwave, dishwasher, coffee/tea maker
Tranquil Tumalo Home
10.0 out of 10, Exceptional, (10)
"Clean and smooth"
The price is NZ$377
includes taxes & fees
29 May - 30 May
Tranquil Tumalo Home
Aerial view
"Otter Sight" Riverside Cottage - Just Steps from the Deschutes
9.4 out of 10, Exceptional, (26)
"The location for walking is great - easy walk into town or out into nature. Only recommendations would be to replace the mattress on the bed - not very comfortable and an extra blanket for the trundle bed - a half quilt and a throw not enough. Otherwise the room has everything needed for a few days or even weeks."
"Otter Sight" Riverside Cottage - Just Steps from the Deschutes
Fridge, microwave, oven, stovetop
Pool Table, Gourmet Kitchen, Outdoor Living
9.4 out of 10, Exceptional, (59)
"The home worked well for our stay. The furniture was comphy and the kitchen was stocked well with supplies. The pool table was a lot of fun and the backyard was great. The management team was quick to respond with support. The alarm was a problem and the bathroom floors were dirty, left over hair and debris. No shampoo or soap was left for us. The master bedroom didnt not have any window covers the first night. The management team was quick to bring them over the next day but they were broken....
Pool Table, Gourmet Kitchen, Outdoor Living
Fridge, microwave, oven, stovetop
LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.
9.4 out of 10, Exceptional, (6)
"This house is in an amazing location! Walking distance to several breweries, restaurants and shops. Having the paddle boards, tubes and bikes at the house made floating the river too easy."
LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.
Fridge, microwave, oven, stovetop
A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage
9.8 out of 10, Exceptional, (90)
"This property would be great for families. It was a little much for just the two of us."
A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage
Fridge, microwave, oven, stovetop
Inviting home with private hot tub & deck - walk to cafes, breweries & the river
9.6 out of 10, Exceptional, (46)
"My buddies and I enjoyed our stay here for a long ski-trip weekend. The house was everything as advertised, clean, and convenient. The location is great, we walked to several breweries and the local food truck lot. Definitely recommend!"
Inviting home with private hot tub & deck - walk to cafes, breweries & the river
Exterior
River View Condo, Close To Town/Mountain, Private Hot Tub
10.0 out of 10, Exceptional, (151)
"We love this unit! We will book again soon for next year!"
River View Condo, Close To Town/Mountain, Private Hot Tub
Exterior
"Mount Your Blessings"-Upscale condo on edge of downtown
9.6 out of 10, Exceptional, (18)
"Comfortable spot with a great use of space and design. Quick access to Deschutes river trail for pleasant walks along the river. Enjoyed my two nights."
The price is NZ$415
includes taxes & fees
23 Jun - 24 Jun
"Mount Your Blessings"-Upscale condo on edge of downtown
Fridge, microwave, oven, stovetop
Perfect Bend Bungalow, Fireplace, A/C, Walk to Everything!
9.4 out of 10, Exceptional, (84)
"The house had a really great layout with the bedrooms all upstairs and a wide open downstairs area that was great for hanging out. Being able to walk to coffee shops and restaurants was a good bonus."
Perfect Bend Bungalow, Fireplace, A/C, Walk to Everything!
Don't see what you're looking for?
See all available properties in Prineville
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.

Other types of properties in Prineville you may be interested in

Exterior
Country Inn & Suites by Radisson, Prineville, OR
2.5 star property
9.2 out of 10, Wonderful, (986)
"We’ve stayed here multiple times and everything has been clean and well kept. Their breakfast is pretty good. My one complaint now that this has happened twice in a row is that I select “pay at hotel” and both times they have charged my card before I have gotten there. "
The price is NZ$248
includes taxes & fees
31 May - 1 Jun
Country Inn & Suites by Radisson, Prineville, OR
Lobby
Best Western Prineville Inn
2.5 star property
8.8 out of 10, Excellent, (712)
"Great "
The price is NZ$232
includes taxes & fees
29 May - 30 May
Best Western Prineville Inn
Standard Room, 1 Queen Bed, Non Smoking
Econo Lodge
2.0 star property
7.0 out of 10, Good, (303)
"I found some clothing under the bed. Bed was too soft and not comfortable. Not all outlets were working. The manager was very helpful in getting the TV to work - the remote should be replaced as the batteries are taped in."
The price is NZ$156
includes taxes & fees
29 May - 30 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Prineville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Prineville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Prineville. Seeing all the best attractions is bound to make you fall in love with Prineville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Prineville short-term rentals, that won’t be hard to do.

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?

Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown: This holiday home rental outside of Prineville is located near skiing, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Prineville?

Choose from 12 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 National Forest and Ochoco Creek Park.

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.

Recent reviews of Prineville properties
Expedia verified reviews

Waypoint Hotel

Waypoint Hotel

5/5 Excellent
"Cassie at the front desk was friendly and helpful. Our room was clean (pictures online are accurate). We enjoyed the fireplaces outside. Would definitely stay again. "
A verified traveller stayed at Waypoint Hotel
Posted 11 hours ago
Waypoint Hotel