Lake Oswego Guest Houses

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Guest Houses in Lake Oswego

Portland International Guesthouse

2185 NW Flanders St Portland OR

$90 nightly

$108 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Portland International Guesthouse in Portland (Northwest Portland), you'll be within a 5-minute drive of Portland State University and Portland Japanese Garden.

Breakfast included

Free WiFi

Evermore Guesthouse

3860 SE Clinton Street Portland OR

$138 nightly

$164 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Portland (Southeast Portland), Evermore Guesthouse is within a 5-minute drive of Reed College and Aladdin Theater.

Breakfast included

Free WiFi

Remodeled Guesthouse with separate Riverfront Patio and dock+river access

Milwaukie OR

$305 nightly

$310 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse in Milwaukie (Oak Grove), you'll be within a 15-minute drive of Oregon Health and Science University and Willamette River.

Pet friendly

Free WiFi

Light and bright family-friendly cottage

Portland OR

With a stay at this guesthouse in Portland (Southeast Portland), you'll be within a 15-minute drive of Moda Center and Oregon Health and Science University.

Free WiFi

Air conditioning

Two Rivers Tiny Red Gem

portland OR

$196 nightly

$231 total

Dec 16 - Dec 17

Total with taxes and fees

Located in Portland (Northeast Portland), this guesthouse is within a 10-minute drive of Moda Center and Oregon Convention Center.

Pet friendly

Free WiFi

Elegant apartment in Eastmoreland

Portland OR

With a stay at this guesthouse in Portland (Southeast Portland), you'll be within a 15-minute drive of Moda Center and Oregon Health and Science University.

Magic Barn, Walk Score 93!

Portland OR

$129 nightly

$154 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this guesthouse in Portland (Southeast Portland), you'll be within a 10-minute drive of Moda Center and Oregon Convention Center.

Hot Tub

Free WiFi

The Multnomah Guest House

Portland OR

With a stay at this guesthouse, you'll be centrally located in Portland, within a 10-minute drive of Portland State University and Oregon Health and Science University.

Air conditioning

Parking available

Spacious, peaceful tiny house retreat, half a block to Alberta Arts District

Portland OR

With a stay at this guesthouse in Portland (Northeast Portland), you'll be within a 10-minute drive of Moda Center and Oregon Convention Center.

Free WiFi

Air conditioning

HotTub, Fast WiFi, cozy & convenient-Casita Morado

Portland OR

With a stay at this guesthouse in Portland (Northeast Portland), you'll be within a 10-minute drive of Moda Center and Oregon Convention Center.

Hot Tub

Air conditioning

{Lake Front Fun} The Little Cottage on West Bay of Lake Oswego

Lake Oswego OR

With a stay at this guesthouse in Lake Oswego, you'll be on the waterfront, within a 10-minute drive of Washington Square Mall and Bridgeport Plaza Mall.

Free WiFi

Air conditioning

Lovely "Wine Country Casita" - Private Guesthouse, Beautiful Views

Sherwood OR

Located in Sherwood, this guesthouse is in the mountains, a 5-minute drive from Tualatin River National Wildlife Refuge and 8 minutes from Chehalem Winery.

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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.