Holiday rentals in Oswego Lake

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Top-rated holiday rentals in Oswego Lake

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

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Top guest favourite
An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.
Guest house in West Linn
4.97 out of 5 average rating, 177 reviews

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.

Guest favourite
Treehouse in Portland
4.82 out of 5 average rating, 530 reviews

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

Guest favourite
A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.
Guest house in Portland
4.93 out of 5 average rating, 160 reviews

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

Top guest favourite
A tree-lined pathway leads to a wooden staircase bordered by blooming flowers. The pathway features a gentle slope with a railing, guiding visitors toward a secluded entrance nestled among greenery. Lush foliage and vibrant blooms provide a natural, tranquil setting.
Guest house in Lake Oswego
4.95 out of 5 average rating, 416 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. It has separate entrance and located at secluded hilly area. There are 8-9 steps to the unit and maybe difficult for some guests. 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.

Top guest favourite
A bright, modern room features a Queen Murphy bed with crisp white linens and yellow accent pillows. Two windows allow natural light, with views of a fenced outdoor space, enhancing the airy atmosphere. A small built-in sofa is positioned beside the bed, offering additional seating.
Guest suite in Milwaukie
4.99 out of 5 average rating, 327 reviews

Room In Between

Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

Top guest favourite
An open and airy living area features a light-colored sectional sofa with a navy throw, centered on a patterned area rug. A coffee table sits in front, and a television is positioned nearby. The space is complemented by dining and kitchen areas in the background.
Guest suite in Milwaukie
4.95 out of 5 average rating, 102 reviews

Spacious and Private Place with a BIG Yard

Private and quiet space with over 800sq/ft of living space. Big living room and fully stocked kitchen. Relax in a queen sized bed next to an indoor fireplace. Kick back in the open concept space. Plenty of natural sunlight, separate key code entrance, and a big gated yard. 15 min to downtown Portland. Plenty of parking, close to the river and next door to a park which has tennis and basketball courts and is wonderful to walk and great for dogs. Can’t wait for your Portland

Top guest favourite
A charming guesthouse is nestled within a lush garden, surrounded by colorful flowering bushes and sculpted hedges. The structure features large windows that offer a glimpse of the serene interior. The path leading to the guesthouse is intertwined with greenery, enhancing the tranquil atmosphere.
Cottage in Portland
4.92 out of 5 average rating, 472 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.

Guest favourite
The exterior of a charming white house is visible, featuring a sloped roof and large front windows. Two black chairs are positioned on the porch, surrounded by a lush green lawn and mature trees, creating a serene outdoor setting.
Home in Lake Oswego
4.88 out of 5 average rating, 199 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

Top guest favourite
A charming tiny house is visible, framed by tall trees and lush greenery. The exterior features a sloped roof, with large windows offering natural light. Stone steps lead to the entrance, which is surrounded by vibrant foliage and a serene path, emphasizing the privacy of the retreat.
Home in Portland
4.92 out of 5 average rating, 106 reviews

Charming Tiny Forest Home, PDX next to Lake Oswego

Relax at this serene Portland retreat on the Lake Oswego border, near Tryon Creek State Park and Lewis & Clark College in the prestigious Dunthorpe neighborhood. Explore the park, bike, hike, swim the river, and sample top local cuisine and wine at two of Willamette Valley’s best tasting rooms, all just minutes away in downtown Lake Oswego. A quick 10 minute drive takes you to downtown Portland and Portlandia! One-night weekend stays require approval.

Top guest favourite
A compact kitchen area features a farmhouse sink with a decorative faucet and a wooden countertop. Shelves hold glassware and dishware, while a coffee maker and other appliances are neatly arranged. Soft lighting creates a welcoming environment for meal preparation.
Guest suite in Lake Oswego
4.93 out of 5 average rating, 743 reviews

The Hen Den

Light filled and cozy 600 sf private 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.

Top guest favourite
A fully mirrored room creates an immersive experience with soft blue mood lighting. A thick mat covered with clean linens and pillows is laid out for sleeping. The reflections on the mirrored walls enhance the unique ambiance, inviting guests to rest and explore.
Home in Lake Oswego
4.97 out of 5 average rating, 272 reviews

Signal House – Light Up The Portal

Signal House is an immersive art home from The Book of Houses in Pudding Heroes – a living chapter of the story. It is an overnight experiential stay, 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. 15 minutes from Portland on I-5.

Top guest favourite
A cozy living area features a green sofa with decorative pillows and a wooden coffee table. A dining table with high chairs is visible in the background, alongside a kitchen area equipped with modern appliances and light-colored cabinetry.
Guest suite in West Linn
4.96 out of 5 average rating, 522 reviews

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.

Popular amenities for Oswego Lake holiday rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Clackamas County
  5. Lake Oswego
  6. Oswego Lake