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Holiday rentals in Lake Oswego

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Top-rated holiday rentals in Lake Oswego

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest suite in Lake Oswego

4.95 out of 5 average rating, 270 reviews

The Lake Oswego Guesthouse

Lovely, private guesthouse located in an upscale, residential Lake Oswego neighborhood. Lake Oswego shops, restaurants, parks, Oswego Lake and farmer's market (open seasonally) are all very close by. Quick and easy drive or bus ride into downtown Portland (approx 15 min drive). The Studio is located above our garage - a comfortable queen bed with high end linens, kitchenette including small refrigerator and coffee/tea making equipment, living room with cable tv and workspace with wifi.

27 Aug – 3 Sep

$229 SGD per night

Guest favourite

Guest house in Lake Oswego

4.96 out of 5 average rating, 310 reviews

Cozy and Charming

The studio unit has a queen size bed equipped with full kitchen and bathroom as well as working area with wifi and HBO, Showtime and other cable programs. This studio unit has separate entrance and located at secluded and quiet area. There are 8-9 steps to the unit. Washer/dryer are in the house, guests can let us know if they like to use. During a winter snow/ice storm, our location can be challenging. Accordingly, you should have a suitable vehicle for safe travel.

27 Jun – 4 Jul

$127 SGD per night

Guest favourite

Cottage in Portland

4.91 out of 5 average rating, 363 reviews

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

18–25 Nov

$231 SGD per night

Guest favourite

Cottage in Lake Oswego

4.93 out of 5 average rating, 227 reviews

Peacock Grove Cottage in Lake Oswego, OR

Sunny, private one bedroom cottage in quiet, wooded neighborhood. Separate dwelling behind main house. Queen bed, sofa bed, TV, WiFi, A/C, full kitchen, washer & dryer, bathroom with shower and beautiful patio. One mile from I-5 and 8 miles to downtown Portland. Short drive to downtown Lake Oswego. Walking distance, just two blocks, to La Provence, Jefe, Zupans, Albertsons, Starbucks, Waluga Park. Perfect for families or the business traveler. Come stay!

26 Oct – 2 Nov

$109 SGD per night

Guest favourite

Guest house in Portland

5.0 out of 5 average rating, 266 reviews

Newly Built Guesthouse with Private Courtyard

Newly built one-bedroom guesthouse with charming private backyard in the popular Maplewood neighborhood. Light-filled, open floor plan with vaulted ceilings. Walk to Maplewood Coffee & Tea. Located 1 ½ miles from Multnomah Village, 3-4 miles from downtown Portland, Lewis & Clark College and OHSU, 7 miles from Nike. Easy day trips to the Oregon Coast, Columbia River Gorge, Mt Hood, and Yamhill County’s Wine Country. ASTR Permit #18-220704-HO

25 Jan – 1 Feb

$208 SGD per night

Guest favourite

Guest house in West Linn

4.93 out of 5 average rating, 340 reviews

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! COVID-19 UPDATE: For Social Distancing get togethers, there is a cozy, covered, and private 12' x 11' outdoor space attached to the cottage, with lights. 4 or 5 people could easily sit over 6 feet apart.

23–30 Jan

$117 SGD per night

Guest house in Lake Oswego

4.85 out of 5 average rating, 145 reviews

Cottage in the Woods: SANITIZED! FULLY STOCKED!

Cute 500 sq foot cottage behind a main house, located on a 1/2 acre park-like setting lot on a dead end street. Quiet location, easy access to I-5, shopping, Lake Oswego, hiking, and the Tualatin River. The cottage has one bedroom w/ a queen bed, blow up queen mattress, and a large couch. The large fir trees on the property attract many birds and squirrels. We also have a flock of neighborhood peacocks that visit!

13–20 Sep

$139 SGD per night

Guest favourite

Guest suite in West Linn

4.96 out of 5 average rating, 300 reviews

Studio in-law suite just south of PDX

Recently updated pricing and NOW NO CLEANING FEES! Quiet basement studio with efficiency kitchen and full bath with rain shower. Located a short distance south of downtown Portland, West Linn is a quiet suburb on the Willamette River. Our home is walkable to a great pub, groceries and other restaurants. This listing includes a lofted queen bed with charming barn door for privacy.

23–30 May

$181 SGD per night

Guest favourite

Guest house in Portland

4.97 out of 5 average rating, 458 reviews

Private & Cozy Casita

Private unattached ADU, new, cute and comfortable, light and bright, off-street parking, quiet neighborhood, close to public transportation, 10 minutes from downtown, hiking trails, parks, near Portland Community College, one hour to the beach, one hour to Mt Hood. Portland is known for its good food, breweries, wineries, coffee shops, shopping, all close by.

16–23 Nov

$137 SGD per night

Guest favourite

Guest suite in Portland

4.93 out of 5 average rating, 195 reviews

Chez Modern

Private modern guest house near Multnomah Village and Gabriel Park. Just 10 minutes from downtown Portland, tucked away in the SW hills on a forested half-acre property. Unit has a private driveway, a full kitchen, full bath, full laundry, 1 bedroom and a deep sofa. Heated floor, AC, rain shower. Walk or bike to bars, restaurants, shops, etc.

6–13 Dec

$162 SGD per night

Guest favourite

Guest suite in West Linn

5.0 out of 5 average rating, 207 reviews

Private Casita in Historic Willamette

Located in the highly desired Historic Willamette district of West Linn, this newly-built casita provides a private bedroom and bathroom with its own entrance. Enjoy walking to restaurants, coffee shops, beer pubs, wine bars, and retail shopping all within several blocks, or take a stroll to the Willamette Park just six blocks south.

9–16 Mar

$177 SGD per night

Guest favourite

Guest suite in Lake Oswego

4.95 out of 5 average rating, 196 reviews

Private Lake Oswego Guest Cottage

Beautiful cottage in Lake Oswego's quiet and scenic First Addition neighborhood. The cottage is spacious, comfortable, and has everything you need to feel at home. It's an easy walk to parks, restaurants, grocery stores, shops, Tryon Creek hiking trails, and a short drive to Portland (10 min)!

20–27 Oct

$270 SGD per night

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Popular amenities for Lake Oswego holiday rentals

Free parking on premises

Air conditioning

Stay near Lake Oswego's top sights

Tryon Creek State Natural Area137 locals recommend

Oswego Grill16 locals recommend

McMenamins John Barleycorns8 locals recommend

Salt & Straw19 locals recommend

Babica Hen Cafe23 locals recommend

Zupan's Markets - Lake Oswego12 locals recommend

Other great holiday rentals in Lake Oswego

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 775 reviews

Granny Flat in leafy SW Portland

26 Apr – 3 May

$175 SGD per night

Guest favourite

Home in Lake Oswego

4.88 out of 5 average rating, 121 reviews

Charming 1-bedroom house with partial lake view

16–23 Oct

$317 SGD per night

Guest favourite

Flat in Portland

4.99 out of 5 average rating, 211 reviews

Lewis and Clark Hide-A-Way Apartment

14–21 Jan

$132 SGD per night

Guest favourite

Guest suite in Milwaukie

4.96 out of 5 average rating, 376 reviews

River Forest Lake Apt w/hot tub. HOT find!

23–30 Mar

$189 SGD per night

Guest favourite

Guest suite in Milwaukie

4.98 out of 5 average rating, 260 reviews

Light Filled Garden Studio

20–27 Oct

$151 SGD per night

Guest favourite

Guest suite in Portland

4.94 out of 5 average rating, 242 reviews

Relax in a Peaceful Forest Retreat, close to town

16–23 Aug

$165 SGD per night

Guest favourite

Guest house in Portland

4.97 out of 5 average rating, 541 reviews

The Westmoreland Lighthouse - Private studio in SE

26 Apr – 3 May

$150 SGD per night

Guest favourite

Yurt in Portland

4.99 out of 5 average rating, 1209 reviews

Garden Home Backyard Yurt Experience

27 Mar – 3 Apr

$122 SGD per night

Quick stats about holiday rentals in Lake Oswego

Total rentals
190 properties
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
10K reviews

Destinations to explore