Book Holiday Homes in Oregon

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Featured Holiday Homes in Oregon

The River House. 5 miles from Crater Lake entrance.

The River House. 5 miles from Crater Lake entrance.

Fort Klamath
With a stay at this vacation home in Fort Klamath, you'll be on a river, within a 10-minute drive of Crater Lake National Park and Fort Klamath Park and ...
The River House. 5 miles from Crater Lake entrance.
Cozy townhome | Close to Haystack | Dog-friendly

Cozy townhome | Close to Haystack | Dog-friendly

Cannon Beach
With a stay at this vacation home in Cannon Beach (Downtown Cannon Beach), you'll be a 4-minute walk from Cannon Beach and within a 5-minute drive of Haystack ...
Cozy townhome | Close to Haystack | Dog-friendly
Charming oceanview | Dog-friendly | Steps to sand

Charming oceanview | Dog-friendly | Steps to sand

Cannon Beach
With a stay at this vacation home in Cannon Beach (Downtown Cannon Beach), you'll be a 3-minute walk from Cannon Beach and within a 5-minute drive of Haystack ...
Charming oceanview | Dog-friendly | Steps to sand
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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
Water view retreat with scenic deck, grill, yard, fireplace, board games, & W/D

Water view retreat with scenic deck, grill, yard, fireplace, board games, & W/D

Bay City
With a stay at this vacation home in Bay City, you'll be within a 10-minute drive of Tillamook Creamery and Tillamook Country Smoker.
Water view retreat with scenic deck, grill, yard, fireplace, board games, & W/D
The Landing at Newport

The Landing at Newport

3 out of 5
890 SE Bay Blvd, Newport, OR
With a stay at The Landing at Newport in Newport, you'll be in the historical district, within a 5-minute drive of Nye Beach and Pacific Maritime and Heritage ...
The Landing at Newport
Dog-Friendly Oceanview Condo with Great Location & Nearby Beach Access

Dog-Friendly Oceanview Condo with Great Location & Nearby Beach Access

Lincoln City
With a stay at this vacation home in Lincoln City, you'll be by the sea, within a 15-minute drive of Chinook Winds Casino and Theatre West.
Dog-Friendly Oceanview Condo with Great Location & Nearby Beach Access
Surf, sand, kites, wave jumping are magical from this large beachfront home.

Surf, sand, kites, wave jumping are magical from this large beachfront home.

Lincoln City
With a stay at this vacation home in Lincoln City, you'll be on the beach, within a 10-minute drive of Chinook Winds Casino and D River State Recreation ...
Surf, sand, kites, wave jumping are magical from this large beachfront home.
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

Troutdale
With a stay at this vacation home in Troutdale, you'll be a 1-minute drive from Columbia River Gorge National Scenic Area and 6 minutes from Sandy River.
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood
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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.

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

Holiday houses in 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 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 Oregon adventures, obvs.

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

Oregon Holiday Homes essential information

Accommodation
9517 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The River House. 5 miles from Crater Lake entrance., Cozy townhome | Close to Haystack | Dog-friendly, Charming oceanview | Dog-friendly | Steps to sand, Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo, Water view retreat with scenic deck, grill, yard, fireplace, board games, & W/D, The Landing at Newport, Dog-Friendly Oceanview Condo with Great Location & Nearby Beach Access, Surf, sand, kites, wave jumping are magical from this large beachfront home., Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

Top trending hotels in Oregon

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
With a stay at The Paramount Hotel, you'll be centrally located in Portland, steps from Arlene Schnitzer Concert Hall and within a 5-minute walk of Portland ...
The Paramount Hotel
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
Courtyard by Marriott Portland City Center is centrally located in Portland, a 4-minute walk from Pioneer Courthouse Square and 8 minutes by foot from Portland ...
Courtyard by Marriott Portland City Center
Valley River Inn

Valley River Inn

3.5 out of 5
1000 Valley River Way, Eugene, OR
Fully refundableReserve now, pay when you stay
When you stay at Valley River Inn in Eugene, you'll be on the riverwalk, a 5-minute drive from Autzen Stadium and 5 minutes from University of Oregon.
Valley River Inn
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Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
With a stay at Holiday Inn Airport - Portland by IHG in Portland (Northeast Portland), you'll be a 4-minute drive from Cascade Station and 11 minutes from Lloyd ...
Holiday Inn Airport - Portland by IHG
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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.