Book Holiday Homes in Oregon

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Oregon

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
Elegant & Modern, 3 Min. Walk to SHARC & Passes, Hot Tub, Fireplace, Bikes

Elegant & Modern, 3 Min. Walk to SHARC & Passes, Hot Tub, Fireplace, Bikes

Sunriver
Book a stay at this family-friendly vacation home in Bend. Enjoy free WiFi, a water park, and patios. Popular attractions Sunriver Homeowners Aquatic & Recreation ...
Elegant & Modern, 3 Min. Walk to SHARC & Passes, Hot Tub, Fireplace, Bikes
Ocean Front Luxury Home

Ocean Front Luxury Home

Gleneden Beach
Book a stay at this beach vacation home in Gleneden Beach. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. ...
Ocean Front Luxury Home
Save an average of 15% on thousands of hotels when you're signed in
Designer Owned House on Vibrant Williams Avenue near Mississippi

Designer Owned House on Vibrant Williams Avenue near Mississippi

Portland
The price is NZ$539 per night from 5 Jan to 6 Jan
NZ$539
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Portland. Enjoy free WiFi, a garden, and patios. Popular attractions Moda Center and Oregon Zoo are located nearby.
Designer Owned House on Vibrant Williams Avenue near Mississippi
Hot Tub, Steps to Deschutes River, SHARC Passes, Ping Pong, Foosball

Hot Tub, Steps to Deschutes River, SHARC Passes, Ping Pong, Foosball

Bend
Book a stay at this family-friendly vacation home in Bend. Enjoy free WiFi, a water park, and tennis courts. Popular attractions Fort Rock Park and Sunriver ...
Hot Tub, Steps to Deschutes River, SHARC Passes, Ping Pong, Foosball
Remodeled! Close to Village, SHARC Passes, Hot Tub, Bikes, Luxury Linens

Remodeled! Close to Village, SHARC Passes, Hot Tub, Bikes, Luxury Linens

Sunriver
Book a stay at this family-friendly vacation home in Bend. Enjoy a water park, tennis courts, and patios. Popular attractions The Village and Sunriver Homeowners ...
Remodeled! Close to Village, SHARC Passes, Hot Tub, Bikes, Luxury Linens
A/C, Hot Tub, 3 King Beds, Easy Walk to SHARC-includes passes & Ft Rock Park, Bikes

A/C, Hot Tub, 3 King Beds, Easy Walk to SHARC-includes passes & Ft Rock Park, Bikes

Sunriver
Book a stay at this family-friendly vacation home in Bend. Enjoy a water park, tennis courts, and patios. Popular attractions Fort Rock Park and Sunriver Homeowners ...
A/C, Hot Tub, 3 King Beds, Easy Walk to SHARC-includes passes & Ft Rock Park, Bikes
Sensational Designer's Townhouse in the heart of Eagle Crest.

Sensational Designer's Townhouse in the heart of Eagle Crest.

Redmond
Stay at this vacation home in Redmond. Enjoy tennis courts, patios, and air conditioning. Popular attractions Eagle Ridge Sports Center and Spa and Juniper Trailhead ...
Sensational Designer's Townhouse in the heart of Eagle Crest.
Isolated beach front house

Isolated beach front house

Otter Rock
Stay at this vacation home in Otter Rock. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attractions Flying Dutchman Winery and ...
Isolated beach front house
Don't see what you're looking for?
See all available properties in Oregon
View all properties
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
7439 Holiday Homes
Lowest Price
NZ$155
Highest Price
NZ$539
Popular accommodation
The Landing at Newport, Elegant & Modern, 3 Min. Walk to SHARC & Passes, Hot Tub, Fireplace, Bikes, Ocean Front Luxury Home, Designer Owned House on Vibrant Williams Avenue near Mississippi, Hot Tub, Steps to Deschutes River, SHARC Passes, Ping Pong, Foosball, Remodeled! Close to Village, SHARC Passes, Hot Tub, Bikes, Luxury Linens, A/C, Hot Tub, 3 King Beds, Easy Walk to SHARC-includes passes & Ft Rock Park, Bikes, Sensational Designer's Townhouse in the heart of Eagle Crest. , Isolated beach front house

Top trending hotels in Oregon

Holiday Inn Airport - Portland, an IHG Hotel

Holiday Inn Airport - Portland, an IHG Hotel

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
The price is NZ$183 per night from 27 Dec to 28 Dec
NZ$183
includes taxes & fees
27 Dec - 28 Dec
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, an IHG 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
The price is NZ$189 per night from 26 Dec to 27 Dec
NZ$189
includes taxes & fees
26 Dec - 27 Dec
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
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave, Portland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$155 per night from 31 Dec to 1 Jan
NZ$155
includes taxes & fees
31 Dec - 1 Jan 2025
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, a free airport shuttle, and a fitness center. Our guests praise the helpful staff and ...
Red Lion Hotel Portland Airport
Save an average of 15% on thousands of hotels when you're signed in
Moxy Portland Downtown

Moxy Portland Downtown

3 out of 5
585 SW 10TH AVENUE, Portland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 26 Dec to 27 Dec
NZ$199
includes taxes & fees
26 Dec - 27 Dec
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, 4 restaurants, and a fitness center. Our guests praise the helpful staff and the clean ...
Moxy Portland Downtown
Don't see what you're looking for?
See all available properties in Oregon
View all properties
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.