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Featured Holiday Homes in Prineville

Historic Belle Millhouse in Bend, OR.  Walk to Downtown.vrbo

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

Bend
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo
Adorable Bend townhome with ideal location, kitchenette & central AC

Adorable Bend townhome with ideal location, kitchenette & central AC

Bend
With a stay at this vacation home in Bend (Century West), you'll be a 5-minute drive from Hayden Homes Amphitheater and 6 minutes from Old Mill District.
Adorable Bend townhome with ideal location, kitchenette & central AC
Sensational Designer's Townhouse in the heart of Eagle Crest.

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

Redmond
Located in Redmond, this vacation home is within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Sensational Designer's Townhouse in the heart of Eagle Crest.
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Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks

Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks

Bend
With a stay at this vacation home in Bend (Larkspur), you'll be within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks
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
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Hayden Homes Amphitheater and Old Mill District.
Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub
Two Saddle Estate | Brasada Ranch | 5200 SF!

Two Saddle Estate | Brasada Ranch | 5200 SF!

Powell Butte
With a stay at this vacation home in Powell Butte, you'll be 22 mi (35.3 km) from Old Mill District and 22.7 mi (36.5 km) from Hayden Homes Amphitheater.
Two Saddle Estate | Brasada Ranch | 5200 SF!
Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop

Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop

2.5 out of 5
Redmond
When you stay at this vacation home in Redmond, you'll be on a river, within a 5-minute drive of Eagle Ridge Sports Center and Spa and Eagle Crest Golf ...
Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop
Heart of Bend-Walkable, Ping Pong, Billards

Heart of Bend-Walkable, Ping Pong, Billards

Bend
With a stay at this vacation home, you'll be centrally located in Bend, a 5-minute drive from Old Mill District and 6 minutes from Hayden Homes ...
Heart of Bend-Walkable, Ping Pong, Billards
Lodge Vibes in the City - Large Log Home

Lodge Vibes in the City - Large Log Home

Bend
With a stay at this vacation home in Bend (Mountain View), you'll be within a 15-minute drive of Old Mill District and Hayden Homes Amphitheater.
Lodge Vibes in the City - Large Log Home
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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
1111 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo, Adorable Bend townhome with ideal location, kitchenette & central AC, Sensational Designer's Townhouse in the heart of Eagle Crest. , Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks, Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub, Two Saddle Estate | Brasada Ranch | 5200 SF!, Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop, Heart of Bend-Walkable, Ping Pong, Billards, Lodge Vibes in the City - Large Log Home

Top trending hotels in Prineville

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
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 ...
Country 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
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 ...
High Desert Inn
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
Located in Prineville, Best Western Prineville Inn is within a 5-minute drive of Ochoco Creek Park and A.R. Bowman Museum.
Best Western Prineville Inn
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Days Inn by Wyndham Bend

Days Inn by Wyndham Bend

2 out of 5
849 NE Third Street, Bend, OR
Fully refundableReserve now, pay when you stay
With a stay at Days Inn by Wyndham Bend, you'll be centrally located in Bend, within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Days Inn by Wyndham Bend
Don't see what you're looking for?
See all available properties in Prineville
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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.

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^Subject to availability and chosen travel dates.