Book Holiday Homes in Lake Oswego

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 Lake Oswego

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of Oregon Convention Center and Moda Center.
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row
Large Cozy Home

Large Cozy Home

Happy Valley
The price is AU$612 per night from 4 Mar to 5 Mar
AU$612
includes taxes & fees
4 Mar - 5 Mar
With a stay at this vacation home in Happy Valley (Southgate), you'll be within a 5-minute drive of Clackamas Town Center and Kaiser Permanente Sunnyside Medical ...
Large Cozy Home
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

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

Troutdale
The price is AU$302 per night from 23 Feb to 24 Feb
AU$302
includes taxes & fees
23 Feb - 24 Feb
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
Save an average of 15% on thousands of hotels when you're signed in
Exquisite Historic Suite Close to Downtown  14-21673

Exquisite Historic Suite Close to Downtown 14-21673

Portland
The price is AU$292 per night from 23 Feb to 24 Feb
AU$292
includes taxes & fees
23 Feb - 24 Feb
With a stay at this vacation home, you'll be centrally located in Portland, a 4-minute drive from Portland State University and 9 minutes from Oregon Convention ...
Exquisite Historic Suite Close to Downtown 14-21673
Lush Paradise 4 BR/2BA~Next to Park~ Walkscore 98

Lush Paradise 4 BR/2BA~Next to Park~ Walkscore 98

Portland
With a stay at this vacation home in Portland (Northeast Portland), you'll be a 4-minute drive from Oregon Convention Center and 5 minutes from Moda Center.
Lush Paradise 4 BR/2BA~Next to Park~ Walkscore 98
Gem in Milwaukie 2 bedroom - 2 Bathroom -  Huge yard

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Milwaukie
The price is AU$489 per night from 23 Feb to 24 Feb
AU$489
includes taxes & fees
23 Feb - 24 Feb
With a stay at this vacation home in Milwaukie, you'll be within a 15-minute drive of Oregon Convention Center and Oregon Health and Science University.
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Single Level, Pet Friendly, Fenced Backyard, Close to Nike, Shopping, Portland

Single Level, Pet Friendly, Fenced Backyard, Close to Nike, Shopping, Portland

Beaverton
Located in Beaverton (Cedar Hills), this vacation home is within a 10-minute drive of Oregon Zoo and Washington Square Mall.
Single Level, Pet Friendly, Fenced Backyard, Close to Nike, Shopping, Portland
Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything

Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything

Portland
With a stay at this vacation home in Portland (Northwest Portland), you'll be a 5-minute drive from Portland State University and 5 minutes from Moda ...
Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything
Remodeled one level w/ yard , heart of lake oswego

Remodeled one level w/ yard , heart of lake oswego

Lake Oswego
Located in Lake Oswego, this vacation home is within a 15-minute drive of Washington Square Mall and Portland State University.
Remodeled one level w/ yard , heart of lake oswego
Don't see what you're looking for?
See all available properties in Lake Oswego
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.

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

Holiday houses in Lake Oswego 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 Lake Oswego 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 Lake Oswego adventures, obvs.

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

Lake Oswego Holiday Homes essential information

Accommodation
973 Holiday Homes
Lowest Price
AU$141
Highest Price
AU$612
Popular accommodation
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row, Large Cozy Home, Springdale Farm & Views - the Gorge, Downtown, Mt. Hood, Exquisite Historic Suite Close to Downtown 14-21673, Lush Paradise 4 BR/2BA~Next to Park~ Walkscore 98, Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard, Single Level, Pet Friendly, Fenced Backyard, Close to Nike, Shopping, Portland, Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything, Remodeled one level w/ yard , heart of lake oswego

Top trending hotels in Lake Oswego

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 2 Mar to 3 Mar
AU$180
includes taxes & fees
2 Mar - 3 Mar
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
Hyatt House Portland/Downtown

Hyatt House Portland/Downtown

3 out of 5
2080 SW River Drive, Portland, OR
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 1 Mar to 2 Mar
AU$201
includes taxes & fees
1 Mar - 2 Mar
Hyatt House Portland/Downtown is centrally located in Portland, a 5-minute walk from Oregon Health and Science University and 9 minutes by foot from Portland ...
Hyatt House Portland/Downtown
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 AU$141 per night from 24 Feb to 25 Feb
AU$141
includes taxes & fees
24 Feb - 25 Feb
With a stay at Red Lion Hotel Portland Airport in Portland (Northeast Portland), you'll be within a 15-minute drive of Oregon Convention Center and Moda ...
Red Lion Hotel Portland Airport
Save an average of 15% on thousands of hotels when you're signed in
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 AU$159 per night from 26 Feb to 27 Feb
AU$159
includes taxes & fees
26 Feb - 27 Feb
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
Don't see what you're looking for?
See all available properties in Lake Oswego
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.