Book Holiday Homes in Central Oregon

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Featured Holiday Homes in Central Oregon

A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage

A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage

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.
A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage
Gorgeous! Fenced Yard, AC, Convenient Location

Gorgeous! Fenced Yard, AC, Convenient Location

Bend
With a stay at this vacation home in Bend (Southeast Bend), you'll be within a 10-minute drive of Old Mill District and Hayden Homes Amphitheater.
Gorgeous! Fenced Yard, AC, Convenient Location
LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.

LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.

Bend
With a stay at this vacation home in Bend, you'll be within a 5-minute drive of Hayden Homes Amphitheater and Old Mill District.
LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes.
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Walkable NWX & Galveston, A/C, Views, Fireplace, Updated, Bike & Running Trails

Walkable NWX & Galveston, A/C, Views, Fireplace, Updated, Bike & Running Trails

Bend
With a stay at this vacation home in Bend, you'll be a 4-minute drive from Hayden Homes Amphitheater and 5 minutes from Old Mill District.
Walkable NWX & Galveston, A/C, Views, Fireplace, Updated, Bike & Running Trails
Eagle Crest Resort Townhome. Pool, Pickleball, Tennis, Large Deck, Fireplace

Eagle Crest Resort Townhome. Pool, Pickleball, Tennis, Large Deck, Fireplace

Redmond
With a stay at this vacation home in Redmond, you'll be within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Eagle Crest Resort Townhome. Pool, Pickleball, Tennis, Large Deck, Fireplace
King bed - Pet Friendly - Jameson's Place

King bed - Pet Friendly - Jameson's Place

Bend
The price is AU$468 per night from 29 May to 30 May
AU$468
per night
29 May - 30 May
With a stay at this vacation home in Bend (Larkspur), you'll be within a 10-minute drive of Old Mill District and Hayden Homes Amphitheater.
King bed - Pet Friendly - Jameson's Place
High desert home with mountain views

High desert home with mountain views

Powell Butte
With a stay at this vacation home in Powell Butte, you'll be in the mountains, and 14.2 mi (22.9 km) from Deschutes County Fairgrounds Expo Center and 23 mi ...
High desert home with mountain views
Family-Friendly Home with Upstairs Loft - New Hot Tub Recently Installed

Family-Friendly Home with Upstairs Loft - New Hot Tub Recently Installed

Sisters
A stay at this vacation home places you in the heart of Sisters, within a 15-minute walk of Cliff Clemens Park and Village Green Park.
Family-Friendly Home with Upstairs Loft - New Hot Tub Recently Installed
Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

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.
Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown
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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
1011 Holiday Homes
Lowest Price
AU$133
Highest Price
AU$468
Popular accommodation
A/C, Hot Tub, Ping Pong, Walk to Everything, Perfect Bend Westside Cottage, Gorgeous! Fenced Yard, AC, Convenient Location, LOCATION! Steps from Dining, Brews, Coffee. Firepit. Washer/Dryer. Dog Friendly. Bikes., Walkable NWX & Galveston, A/C, Views, Fireplace, Updated, Bike & Running Trails, Eagle Crest Resort Townhome. Pool, Pickleball, Tennis, Large Deck, Fireplace, King bed - Pet Friendly - Jameson's Place, High desert home with mountain views, Family-Friendly Home with Upstairs Loft - New Hot Tub Recently Installed, Sleek & Modern, A/C, Cozy Retreat, Walk to Downtown

Top trending hotels in Central Oregon

Riverhouse on the Deschutes

Riverhouse on the Deschutes

3.5 out of 5
3075 N. Business 97, Bend, OR
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 23 Jun to 24 Jun
AU$249
per night
23 Jun - 24 Jun
In the heart of Bend, Riverhouse on the Deschutes is within a 5-minute drive of Blockbuster and River's Edge Golf Course.
Riverhouse on the Deschutes
Campfire Hotel

Campfire Hotel

3 out of 5
721 NE 3rd Street, Bend, OR
Fully refundableReserve now, pay when you stay
The price is AU$253 per night from 29 May to 30 May
AU$253
per night
29 May - 30 May
In the heart of Bend, Campfire Hotel is within a 5-minute drive of Pilot Butte State Park and Tower Theater.
Campfire Hotel
Bend Inn & Suites

Bend Inn & Suites

2 out of 5
437 NE 3rd St., Bend, OR
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 29 May to 30 May
AU$133
per night
29 May - 30 May
With a stay at Bend Inn & Suites in Bend (Larkspur), you'll be within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Bend Inn & Suites
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Hotel Peppertree Bend, BW Premier Collection

Hotel Peppertree Bend, BW Premier Collection

3.5 out of 5
1082 SW Yates Dr, Bend, OR
The price is AU$284 per night from 23 Jun to 24 Jun
AU$284
per night
23 Jun - 24 Jun
With a stay at Hotel Peppertree Bend, BW Premier Collection in Bend (Century West), you'll be within a 5-minute drive of Old Mill District and Hayden Homes ...
Hotel Peppertree Bend, BW Premier Collection
Don't see what you're looking for?
See all available properties in Central Oregon
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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.