Holiday rentals in Lake Oswego

Guest house in Lake Oswego

5 out of 5 average rating, 129 reviews

Oswego Empty Nest

The Oswego Empty Nest is a newly remodeled, cozy, one bedroom unit located in Lake Oswego with a private entrance and 500 sq ft of living space. Prepare your own meals in the beautiful full kitchen. Relax, work or entertain yourself in the living space with a large TV with Roku or rest in the quiet comfortable bedroom with an en suite bathroom. Easy access to restaurants, New Seasons, Columbia Outlet, and hiking trails all within walking distance. Close to downtown and quick airport access.

4.96 out of 5 average rating, 136 reviews

Guest house in West Linn

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

4.96 out of 5 average rating, 195 reviews

"OMG! Blow Your Mind! Unbelievable" Cats n Mirrors

The portal is an overnight experiential stay by artist Steven Ochs, for travelers looking to jump off to the next dimension. Our 3 room home's highlight is the fully mirrored experience with sound /mood lighting for play & sleep. We have a cat meme lounging experience in the media room also, both of these have won Best-in-Show at Rose City Comic Con. Private lake access starts June 17 and ends August 27: only blocks away for a wonderful summer trip. We're only 15 minutes from Portland on I-5

Guest house in Lake Oswego

4.97 out of 5 average rating, 102 reviews

Secluded Willamette River Apartment in Lake Oswego

Enjoy a private stay full of nature with a river view! Newly remodeled 1 bedroom private apartment secluded and quiet. Apt is completely separate from main house. 10 min wlk to Mary's Woods Ret. Comm, 20 mins to George Rogers Park, 10 more to DT Lake Oswego w/shops, restaurants and theaters. Private, wooded property along the Willamette River. Fully rmld kit. & BR, LR with large 50” Smart TV, fast wifi. Q-bed + twin in sunroom, table/work area + wa/dr below. 8 stair entrance at back.

Guest house in West Portland Park

4.96 out of 5 average rating, 371 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 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. You may need to cancel or change your reservation accordingly if there are snow/ice storm.

4.95 out of 5 average rating, 126 reviews

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. All bedrooms have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets, one bedroom has a desk and chair for a work space if needed. There is a yoga space set up in the garage w/ mat and mirrors that you are welcome to use. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Home in Beaverton-Hillsboro

4.97 out of 5 average rating, 129 reviews

Maple Cottage - Enchanting, Cozy and Private

Nestled on a quiet treed street in the upscale First Addition neighborhood of Lake Oswego, Maple Cottage is a tastefully decorated single level home waiting for you. Enjoy total privacy! Maple Cottage is cozy and clean. This beautiful 720 sq. ft. private cottage has two bedrooms, one bath, a fully equipped kitchen and a living room where you can relax. Stroll to restaurants, bars, shops, the local movie theater, parks, grocery store and more. First Addition is a walker's paradise.

4.93 out of 5 average rating, 291 reviews

Cottage in Lake Oswego

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!

4.9 out of 5 average rating, 165 reviews

“Sucker Creek Inn” - 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- built when Lake Oswego was known as Sucker Creek

Guest suite in Lake Grove

4.93 out of 5 average rating, 661 reviews

The Hen Den

Light filled and cozy 600 sf guest suite with private entry in a private garden setting. Grill up a burger or head down to the local French restaurant for some tasty food. Rent gear at the REI down the road and head to Mt. Hood for an adventure. Close to Bridgeport Mall and amazing restaurants with easy access to I-5, I-205 and I-117 to head to the coast, the Columbia River Gorge or downtown Portland.

4.95 out of 5 average rating, 407 reviews

Guest suite in West Linn

Evergreen Escape - Relaxing South Metro Studio

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.

Guest house in West Portland Park

4.95 out of 5 average rating, 661 reviews

Portland Cottage with Kitchenette

Our cottage is in a quiet southwest Portland neighborhood. It includes a pillow top queen size bed, microwave, refrigerator, Keurig coffee maker, toaster oven, 2 burner hotplate, hair dryer, soap & shampoo. Easy access to I-5 and downtown Portland by car or public transportation.

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Other great holiday rentals in Lake Oswego

4.89 out of 5 average rating, 47 reviews

Home in Portland

Charming Tiny Forest Home, PDX next to Lake Oswego

JennaRating, 5 stars1 week ago

Super cute and cozy, close to down town, nice walking paths, had everything we needed for a night away.

4.87 out of 5 average rating, 63 reviews

Beautiful Spacious Downstairs Daylight Ranch in LO

EmmetRating, 5 stars2 weeks ago

Our stay was great! The place was very nice and well maintained, and John was proactive in making sure we had a good experience.

Guest house in Lake Oswego

4.84 out of 5 average rating, 182 reviews

Cottage in the Woods: SANITIZED! FULLY STOCKED!

TimRating, 5 stars2 months ago

The cottage was perfect for a traveling couple. Quiet and peaceful surroundings but a 5-minute drive to plenty of shopping and restaurants. Really enjoyed visits from the beautiful peacocks. We will return in September!

4.92 out of 5 average rating, 61 reviews

Guest suite in Milwaukie

Spacious Private BIG Yard

SerenaRating, 5 starstoday

The place was super clean especially for being pet friendly. large very nice yard to hang out in right next to a cute park. cozy and comfy and the hair was super helpful and responsive :)

4.87 out of 5 average rating, 31 reviews

Guest suite in Uplands

The Nook

JennyRating, 5 stars3 days ago

Bret’s place was perfect for a quick overnight stay. The Nook is tucked away making you feel like you’re in your own private space. Loved waking up to the trees and a peaceful view!

5 out of 5 average rating, 52 reviews

New, modern and cozy home on Lakeview

DaleRating, 5 stars5 months ago

Our best Airbnb experience ever We will rent anytime we’re going to be in Portland

Guest suite in Mountain Park

4.88 out of 5 average rating, 199 reviews

~Clean Aloha House in Lovely Lake Oswego~

AnnaRating, 5 stars1 week ago

Annette's place was the cleanest AirBnB I've stayed in. The high end touches like the white rug were cozy and made the place feel like home. Easy to use coffee maker and appreciated the electric kettle. There are very nice (hidden) options for walks in the neighborhood. The community has a network of paved trails that run inbetween houses and by natural areas. To locate the closest trail follow the sidewalk outside the cul-de-sac up the hill, you will very soon be in the trail system. This is a high end neighborhood and feels very safe. I was commuting across I-5 to Tigard and got to my destination in 5'. Trader Joe's and a natural grocery store were also close by. I ended up leaving a few days early because of a crisis at home. Annette offered to reimburse me for the days I couldn't stay, even though it was too late for her to rebook the AirBnB. I thought that was very kind of her.