Book Holiday Homes in Central Oregon

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Featured Holiday Homes in Central Oregon

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
Cabin-style retreat with WiFi, private hot tub, & SHARC access

Cabin-style retreat with WiFi, private hot tub, & SHARC access

Sunriver
Located in Bend (Sunriver), this vacation home is within a 15-minute walk of Sunriver Homeowners Aquatic & Recreation Center and The Village.
Cabin-style retreat with WiFi, private hot tub, & SHARC access
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
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4-bedroom house in charming Sunriver on the golf course. Enjoy your stay

4-bedroom house in charming Sunriver on the golf course. Enjoy your stay

Sunriver
With a stay at this vacation home in Bend (Sunriver), you'll be a 5-minute drive from Fort Rock Park and 6 minutes from Deschutes River.
4-bedroom house in charming Sunriver on the golf course. Enjoy your stay
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
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

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

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

Central Oregon 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 Central Oregon vacation homes are the perfect way for you to wing it.

Holiday houses in Central Oregon 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 Central Oregon 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 Central Oregon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Central Oregon 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 Central Oregon 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.

Central Oregon Holiday Homes essential information

Accommodation
1276 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo, Cabin-style retreat with WiFi, private hot tub, & SHARC access, Adorable Bend townhome with ideal location, kitchenette & central AC, 4-bedroom house in charming Sunriver on the golf course. Enjoy your stay, 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, Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Top trending hotels in Central Oregon

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
Riverhouse Lodge

Riverhouse Lodge

3.5 out of 5
3075 N. Business 97, Bend, OR
Fully refundableReserve now, pay when you stay
In the heart of Bend, Riverhouse Lodge is within a 5-minute drive of Blockbuster and River's Edge Golf Course.
Riverhouse Lodge
La Quinta Inn by Wyndham Bend

La Quinta Inn by Wyndham Bend

3 out of 5
61200 S Highway 97, Bend, OR
Fully refundableReserve now, pay when you stay
With a stay at La Quinta Inn by Wyndham Bend in Bend (Old Farm District), you'll be a 4-minute drive from Old Mill District and 6 minutes from Hayden Homes ...
La Quinta Inn by Wyndham Bend
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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.
Campfire 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.

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^Subject to availability and chosen travel dates.