Book Holiday Homes in Prineville

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Featured Holiday Homes in Prineville

Sensational Designer's Townhouse in the heart of Eagle Crest.

Sensational Designer's Townhouse in the heart of Eagle Crest.

Redmond OR
Located in Redmond, this vacation home is within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Opens in a new windowSensational Designer's Townhouse in the heart of Eagle Crest.
Amazing West Side * 2 King Suites * Walk Everywhere  * 8 Person Hot Tub

Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub

Bend OR
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Old Mill District and Deschutes River.
Opens in a new windowAmazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub
5 Minute Drive to Downtown Bend, Dog Friendly

5 Minute Drive to Downtown Bend, Dog Friendly

Bend OR
With a stay at this vacation home in Bend (Southwest Bend), you'll be within a 5-minute drive of Old Mill District and Deschutes River.
Opens in a new window5 Minute Drive to Downtown Bend, Dog Friendly
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Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Terrebonne OR
The price is AU$478 per night from 8 Jan to 9 Jan
AU$478
8 Jan - 9 Jan 2026
includes taxes & fees
Located in Terrebonne, this vacation home is in a rural location, within a 15-minute drive of Deschutes River and Crooked River Ranch Golf Course.
Opens in a new windowCentral Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
Exquisite Luxury Home with Panoramic Mountain Views & First-Class Amenities

Exquisite Luxury Home with Panoramic Mountain Views & First-Class Amenities

Powell Butte OR
With a stay at this vacation home in Powell Butte, you'll be next to a golf course, and 21.9 mi (35.3 km) from Old Mill District and 13.6 mi (21.8 km) from Redmond ...
Opens in a new windowExquisite Luxury Home with Panoramic Mountain Views & First-Class Amenities
Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat

Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat

Bend OR
With a stay at this vacation home in Bend, you'll be within a 10-minute drive of Old Mill District and Deschutes River.
Opens in a new windowStone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat
Minutes to Deschutes River Trail with Hot Tub & Fire Pit!

Minutes to Deschutes River Trail with Hot Tub & Fire Pit!

Bend OR
With a stay at this vacation home in Bend (Century West), you'll be within a 5-minute drive of Old Mill District and Deschutes River.
Opens in a new windowMinutes to Deschutes River Trail with Hot Tub & Fire Pit!
Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District

Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District

Bend OR
With a stay at this vacation home in Bend (Century West), you'll be within a 5-minute drive of Old Mill District and Deschutes River.
Opens in a new windowBend Getaway in RiverWild-Walk to Deschutes River and Old Mill District
SW Chamberlain Street | Southern Crossing | hot tub pet friendly (dog)

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

Bend OR
With a stay at this vacation home in Bend (Southern Crossing), you'll be within a 10-minute walk of Old Mill District and Deschutes River.
Opens in a new windowSW Chamberlain Street | Southern Crossing | hot tub pet friendly (dog)
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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.

Prineville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Prineville vacation homes are the perfect way for you to wing it.

Holiday houses in Prineville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Prineville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Prineville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Prineville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Prineville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Prineville Holiday Homes essential information

Accommodation
1070 Holiday Homes
Lowest Price
AU$89
Highest Price
AU$478
Popular accommodation
Sensational Designer's Townhouse in the heart of Eagle Crest. , Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub, 5 Minute Drive to Downtown Bend, Dog Friendly, Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace, Exquisite Luxury Home with Panoramic Mountain Views & First-Class Amenities, Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat, Minutes to Deschutes River Trail with Hot Tub & Fire Pit!, Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District, SW Chamberlain Street | Southern Crossing | hot tub pet friendly (dog)

Top trending hotels in Prineville

Best Western Prineville Inn

Best Western Prineville Inn

2.5 out of 5
1475 NE 3rd Street Prineville OR
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 28 Dec to 29 Dec
AU$180
28 Dec - 29 Dec
includes taxes & fees
Located in Prineville, Best Western Prineville Inn is within a 5-minute drive of Ochoco Creek Park and A.R. Bowman Museum.
Opens in a new windowBest Western Prineville Inn
Country Inn & Suites by Radisson, Prineville, OR

Country Inn & Suites by Radisson, Prineville, OR

2.5 out of 5
1773 NE Third Street Prineville OR
Fully refundable
The price is AU$176 per night from 26 Jan to 27 Jan
AU$176
26 Jan - 27 Jan 2026
includes taxes & fees
When you stay at Country Inn & Suites by Radisson, Prineville, OR in Prineville, you'll be in the business district, within a 5-minute drive of Ochoco Creek ...
Opens in a new windowCountry Inn & Suites by Radisson, Prineville, OR
High Desert Inn

High Desert Inn

2 out of 5
123 NE 3rd Street Prineville OR
Fully refundableReserve now, pay when you stay
The price is AU$89 per night from 28 Dec to 29 Dec
AU$89
28 Dec - 29 Dec
includes taxes & fees
With a stay at High Desert Inn in Prineville, you'll be 20.3 mi (32.7 km) from Deschutes County Fairgrounds Expo Center and 23.1 mi (37.1 km) from Smith Rock ...
Opens in a new windowHigh Desert Inn
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Campfire Hotel

Campfire Hotel

3 out of 5
721 NE 3rd Street Bend OR
Fully refundableReserve now, pay when you stay
In the heart of Bend, Campfire Hotel is within a 5-minute drive of Pilot Butte State Park and Tower Theater.
Opens in a new windowCampfire Hotel
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.