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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, 269 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.

23–30 Jul

$229 SGD per night

Guest favourite

Guest house in Lake Oswego

4.96 out of 5 average rating, 307 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.

14–21 Jun

$125 SGD per night

Guest favourite

Guest suite in Portland

4.94 out of 5 average rating, 241 reviews

Super Relaxing Forest Retreat, close to town

Cute + Cozy Apartment in the Forest. 800 sq ft 1 bedroom/1 bath daylight basement apartment. Private entrance, spacious living room w/ sofa bed, balcony and deck, plus a quaint kitchenette. A perfectly peaceful retreat, nestled in the forest yet close to the city. IG: @owlcreekretreat Located in a quiet neighborhood, close to Woods Memorial Park. Just a 3 minute drive to popular Multnomah Village; 15 minutes from Downtown Portland; less than 10 minutes from Lake Oswego.

28 May – 4 Jun

$145 SGD per night

Guest favourite

Cottage in Portland

4.92 out of 5 average rating, 357 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.

29 Sep – 6 Oct

$226 SGD per night

Guest favourite

Cottage in Lake Oswego

4.93 out of 5 average rating, 224 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!

27 Jul – 3 Aug

$108 SGD per night

Guest favourite

Home in Lake Oswego

4.88 out of 5 average rating, 118 reviews

Charming 1-bedroom house with partial lake view

This home is in a great location only a 10 minute walk to downtown Lake Oswego where you'll find a wide variety of restaurants, bars, and shopping. It's also just a five minute walk from the Willamette River, so bring your kayaks and SUPs to explore all that Lake Oswego has to offer, or take a short Uber ride (10 minutes) into downtown Portland. Lastly, the lot is next to one of the oldest homes in Lake Oswego and part of the Lake Oswego historical society.

24–31 Jul

$313 SGD per night

Guest favourite

Guest house in Portland

5.0 out of 5 average rating, 261 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

21–28 Feb

$183 SGD per night

Guest favourite

Guest house in West Linn

4.93 out of 5 average rating, 336 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.

10–17 Feb

$114 SGD per night

Guest house in Lake Oswego

4.84 out of 5 average rating, 140 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!

31 Aug – 7 Sep

$172 SGD per night

Guest favourite

Guest suite in West Linn

4.96 out of 5 average rating, 284 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.

20–27 Feb

$132 SGD per night

Guest favourite

Guest house in Portland

4.97 out of 5 average rating, 452 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.

30 Jan – 6 Feb

$135 SGD per night

Guest favourite

Guest suite in Lake Oswego

4.89 out of 5 average rating, 175 reviews

~Clean Aloha House in Lovely Lake Oswego~

Aloha and welcome to your lovely, quiet and relaxing getaway! You will have private outdoor access to your own bedroom, bathroom, living room and kitchenette. The entire lower level of our home is for you only. Host may need to access the washer/dryer in your unit occasionally. We will always communicate with you first and be non-intrusive.

17–24 Sep

$111 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

4.9 out of 5 average rating, 312 reviews

Multnomah Village Studio

26 Oct – 2 Nov

$100 SGD per night

Guest favourite

Flat in Portland

4.99 out of 5 average rating, 207 reviews

Lewis and Clark Hide-A-Way Apartment

10–17 Oct

$130 SGD per night

Guest favourite

Guest suite in Lake Oswego

4.94 out of 5 average rating, 254 reviews

Peaceful 2 Bdrm Suite 1000 sq ft. Upscale Location

17–24 May

$276 SGD per night

Guest favourite

Guest suite in Tigard

4.97 out of 5 average rating, 149 reviews

Wilson's Guesthouse

16–23 Jul

$171 SGD per night

Guest favourite

Guest suite in Portland

4.93 out of 5 average rating, 195 reviews

Chez Modern

10–17 Dec

$160 SGD per night

Guest favourite

Flat in Lake Oswego

5.0 out of 5 average rating, 5 reviews

Lake Oswego Apartment Studio

23–30 May

$145 SGD per night

Guest favourite

Guest suite in Lake Oswego

4.99 out of 5 average rating, 73 reviews

Peaceful Tree-Lined, Private ADU Retreat

15–22 Aug

$170 SGD per night

Guest favourite

Guest house in Lake Oswego

5.0 out of 5 average rating, 87 reviews

Oswego Empty Nest

3–10 Oct

$193 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

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