Book Holiday Homes in Eastern Oregon

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Featured Holiday Homes in Eastern Oregon

Turn Of The Century Charm  - Walk to Town       DISCOUNTS FOR SKIING?

Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?

Baker City
A stay at this vacation home places you in the heart of Baker City, steps from Crossroads Carnegie Art Center and 4 minutes by foot from Baker City ...
Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?
Dixie Creek Bungalows, Not so Tiny, Tiny Home

Dixie Creek Bungalows, Not so Tiny, Tiny Home

Prairie City
You'll be centrally located in Prairie City with a stay at this vacation home, and 4 minutes by foot from John Day River.
Dixie Creek Bungalows, Not so Tiny, Tiny Home
Beautiful lakefront house with private boat dock, washer/dryer & fireplace

Beautiful lakefront house with private boat dock, washer/dryer & fireplace

Joseph
With a stay at this vacation home, you'll be centrally located in Joseph, within a 5-minute drive of Wallowa Lake and Wallowa River.
Beautiful lakefront house with private boat dock, washer/dryer & fireplace
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Charming riverfront home with fireplace, patio, grill, & full kitchen

Charming riverfront home with fireplace, patio, grill, & full kitchen

Joseph
When you stay at this vacation home in Joseph, you'll be on the waterfront, within a 15-minute walk of Wallowa Lake and Wallowa River.
Charming riverfront home with fireplace, patio, grill, & full kitchen
Moonrise Suite in a Vineyard + Winery!

Moonrise Suite in a Vineyard + Winery!

Milton-Freewater
Located in Milton-Freewater, this farm stay is on a river, within a 15-minute drive of Frazier Farmstead Museum and Old City Cemetery.
Moonrise Suite in a Vineyard + Winery!
The Loft Modern/Historic

The Loft Modern/Historic

Baker City
With a stay at this vacation home in Baker City, you'll be just steps from Baker Tower and Great Salt Lick Sculpture.
The Loft Modern/Historic
Modern on the Rocks - In the Heart of Wine Country

Modern on the Rocks - In the Heart of Wine Country

Milton-Freewater
Located in Milton-Freewater, this vacation home is in a rural location, within a 5-minute drive of The Blue Mountain Cidery and Joe Humbert Family Aquatic ...
Modern on the Rocks - In the Heart of Wine Country
Custom-built log home w/ gas grill, free WiFi, deck, and private location

Custom-built log home w/ gas grill, free WiFi, deck, and private location

Joseph
With a stay at this vacation home in Enterprise, you'll be in the mountains, within a 5-minute drive of Wallowa Lake and Wallowa-Whitman National Forest.
Custom-built log home w/ gas grill, free WiFi, deck, and private location
Waterfront Home on Wallowa Lake with private sauna, dock & amazing view

Waterfront Home on Wallowa Lake with private sauna, dock & amazing view

Joseph
With a stay at this vacation home in Joseph, you'll be on the waterfront, within a 10-minute drive of Wallowa Lake and Wallowa River.
Waterfront Home on Wallowa Lake with private sauna, dock & amazing view
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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.

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

Holiday houses in Eastern 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 Eastern 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 Eastern Oregon adventures, obvs.

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

Eastern Oregon Holiday Homes essential information

Accommodation
194 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?, Dixie Creek Bungalows, Not so Tiny, Tiny Home, Beautiful lakefront house with private boat dock, washer/dryer & fireplace, Charming riverfront home with fireplace, patio, grill, & full kitchen, Moonrise Suite in a Vineyard + Winery!, The Loft Modern/Historic, Modern on the Rocks - In the Heart of Wine Country, Custom-built log home w/ gas grill, free WiFi, deck, and private location, Waterfront Home on Wallowa Lake with private sauna, dock & amazing view

Top trending hotels in Eastern Oregon

Red Lion Hotel Pendleton

Red Lion Hotel Pendleton

3 out of 5
304 Se Nye Ave, Pendleton, OR
Fully refundableReserve now, pay when you stay
With a stay at Red Lion Hotel Pendleton, you'll be centrally located in Pendleton, within a 10-minute drive of Wildhorse Casino and Children's Museum of Eastern ...
Red Lion Hotel Pendleton
Oxford Suites Hermiston

Oxford Suites Hermiston

3 out of 5
1050 N 1st St, Hermiston, OR
Fully refundableReserve now, pay when you stay
When you stay at Oxford Suites Hermiston in Hermiston, you'll be near the airport and 10 minutes by car from Big River Golf Course.
Oxford Suites Hermiston
River Lodge And Grill

River Lodge And Grill

3 out of 5
6 Marine Dr, Boardman, OR
Fully refundableReserve now, pay when you stay
Located in Boardman, River Lodge And Grill is within a 15-minute drive of SAGE Center and Marker 40 Golf Club.
River Lodge And Grill
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Red Lion Inn & Suites Ontario

Red Lion Inn & Suites Ontario

2 out of 5
266 NE Goodfellow St., Ontario, OR
Fully refundable
When you stay at Red Lion Inn & Suites Ontario in Ontario, you'll be in the business district, within a 5-minute drive of Ontario State Park and Treasure Valley ...
Red Lion Inn & Suites Ontario
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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.