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

Gem in Milwaukie 2 bedroom - 2 Bathroom -  Huge yard

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Milwaukie
The price is AU$424 per night from 10 Nov to 11 Nov
AU$424
includes taxes & fees
10 Nov - 11 Nov
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
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

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

Troutdale
The price is AU$291 per night from 8 Nov to 9 Nov
AU$291
includes taxes & fees
8 Nov - 9 Nov
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
Designer Owned House on Vibrant Williams Avenue near Mississippi

Designer Owned House on Vibrant Williams Avenue near Mississippi

Portland
The price is AU$530 per night from 11 Nov to 12 Nov
AU$530
includes taxes & fees
11 Nov - 12 Nov
With a stay at this vacation home, you'll be centrally located in Portland, a 5-minute drive from Oregon Convention Center and 5 minutes from Moda Center.
Designer Owned House on Vibrant Williams Avenue near Mississippi
Save an average of 15% on thousands of hotels when you're signed in
Secluded large home. Wooded setting. Easy commute to downtown.

Secluded large home. Wooded setting. Easy commute to downtown.

Portland
When you stay at this vacation home in Portland, you'll be within a 10-minute drive of Willamette River and Forest Park.
Secluded large home. Wooded setting. Easy commute to downtown.
Camas Lakehouse With Private Hot Tub

Camas Lakehouse With Private Hot Tub

Camas
With a stay at this vacation home in Camas, you'll be on a lake, within a 10-minute drive of Columbia River Gorge National Scenic Area and Lacamas Lake Regional ...
Camas Lakehouse With Private Hot Tub
Estate Surrounded By Trees, Hills, and Farmland, w/ Fire-Pits, Air Hockey, Foosball, BBQ, Pet-Friend

Estate Surrounded By Trees, Hills, and Farmland, w/ Fire-Pits, Air Hockey, Foosball, BBQ, Pet-Friend

Damascus
With a stay at this vacation home in Damascus, you'll be in the mountains, within a 15-minute drive of Columbia River Gorge National Scenic Area and Gresham ...
Estate Surrounded By Trees, Hills, and Farmland, w/ Fire-Pits, Air Hockey, Foosball, BBQ, Pet-Friend
Exquisite Historic Suite Close to Downtown  14-21673

Exquisite Historic Suite Close to Downtown 14-21673

Portland
The price is AU$282 per night from 10 Nov to 11 Nov
AU$282
includes taxes & fees
10 Nov - 11 Nov
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
Large Cozy Home

Large Cozy Home

Happy Valley
The price is AU$640 per night from 11 Nov to 12 Nov
AU$640
includes taxes & fees
11 Nov - 12 Nov
With a stay at this vacation home in Happy Valley (Southgate), you'll be within a 15-minute drive of Hawthorne District and Clackamas Town Center.
Large Cozy Home
Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country

Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country

Yamhill
Located in Newberg, this vacation home is a 4-minute drive from WillaKenzie Estate and 7 minutes from Adea Wine Company.
Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country
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
924 Holiday Homes
Lowest Price
AU$86
Highest Price
AU$640
Popular accommodation
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard, Springdale Farm & Views - the Gorge, Downtown, Mt. Hood, Designer Owned House on Vibrant Williams Avenue near Mississippi, Secluded large home. Wooded setting. Easy commute to downtown. , Camas Lakehouse With Private Hot Tub, Estate Surrounded By Trees, Hills, and Farmland, w/ Fire-Pits, Air Hockey, Foosball, BBQ, Pet-Friend, Exquisite Historic Suite Close to Downtown 14-21673, Large Cozy Home, Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country

Top trending hotels in Lake Oswego

Motel 6 Tigard, OR - Portland South - Lake Oswego

Motel 6 Tigard, OR - Portland South - Lake Oswego

2 out of 5
17950 SW Mcewan Ave, Lake Oswego, OR
Fully refundableReserve now, pay when you stay
The price is AU$86 per night from 24 Nov to 25 Nov
AU$86
includes taxes & fees
24 Nov - 25 Nov
Located in Lake Oswego, Motel 6 Tigard, OR - Portland South - Lake Oswego is a 2-minute drive from Bridgeport Village and 13 minutes from Portland State ...
Motel 6 Tigard, OR - Portland South - Lake Oswego
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$169 per night from 10 Nov to 11 Nov
AU$169
includes taxes & fees
10 Nov - 11 Nov
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
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$149 per night from 20 Nov to 21 Nov
AU$149
includes taxes & fees
20 Nov - 21 Nov
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
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 AU$157 per night from 17 Nov to 18 Nov
AU$157
includes taxes & fees
17 Nov - 18 Nov
With a stay at Holiday Inn Airport - Portland, an IHG Hotel in Portland (Northeast Portland), you'll be a 3-minute drive from Cascade Station and 11 minutes ...
Holiday Inn Airport - Portland, an IHG Hotel
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.