Book Holiday Homes in Oregon

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Explore these top cities in Oregon

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
Stay at this vacation home in Fort Klamath. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions 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
Stay at this vacation home in Cannon Beach. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Cannon Beach and Haystack ...
Cozy townhome | Close to Haystack | Dog-friendly
Charming oceanview | Dog-friendly | Steps to sand

Charming oceanview | Dog-friendly | Steps to sand

Cannon Beach
Stay at this vacation home in Cannon Beach. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Cannon Beach and Haystack Rock ...
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
Book a stay at this ski vacation home in Bend. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Hayden Homes Amphitheater and Old Mill ...
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
Stay at this vacation home in Bay City. Enjoy laundry facilities, a picnic area, and patios. Popular attractions 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
Stay at this 3-star vacation home in Newport. Enjoy free WiFi, free parking, and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this vacation home in Lincoln City. Enjoy balconies, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Chinook Winds Casino ...
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
Book a stay at this beach vacation home in Lincoln City. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this vacation home in Troutdale. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Sandy River and Reed Island State ...
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
9463 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
Stay at this 3.5-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
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
Stay at this 3.5-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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
Stay at this 3.5-star family-friendly hotel in Eugene. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the comfy rooms in our reviews. ...
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
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Holiday Inn Airport - Portland by IHG
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See all available properties in 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.

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^Subject to availability and chosen travel dates.