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, 176 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, 526 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.

Top guest favourite
A detached studio features a charming A-frame design, surrounded by lush greenery. A stone patio with outdoor seating complements the inviting entrance, where large windows allow natural light to fill the space. The setting provides a serene atmosphere, ideal for relaxation.
Guest house in Portland
4.98 out of 5 average rating, 688 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

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, 326 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, 101 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 neatly arranged bedroom features a white metal headboard with soft linens. A pillow with 'Aloha' is centered on the bed. A bedside lamp and a small table book are visible next to the bed, complemented by a subtle wall design that adds texture.
Guest suite in Lake Oswego
4.88 out of 5 average rating, 237 reviews

~Clean Aloha House in Lovely Lake Oswego~

Aloha! Welcome to your quiet, relaxing getaway You’ll have private access to your bedroom, bathroom, living room, and kitchenette. The entire lower level of our home is yours. The host may occasionally need access to the w/d in your unit, but we will always communicate first and be non-intrusive. Please note, we are a quiet family living above, so you may hear footsteps. We do have a golden retriever who is EXTREMELY friendly. He might bark when you arrive to say hello.

Top guest favourite
An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.
Guest house in Portland
4.96 out of 5 average rating, 513 reviews

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Top guest favourite
A private hot tub is prominently positioned, surrounded by lush greenery and tall trees. Nearby, a gas barbecue is visible on a patio, along with a set of two chairs and a small table under a shaded gazebo, creating a serene outdoor dining space.
Cottage in Portland
4.94 out of 5 average rating, 244 reviews

Romantic Urban Oasis in the City-Owl Forest Studio

PORTLAND CITY PERMIT #14-248488-000-00-HO Debi's pronouns: she/her Rob's pronouns: he/him *Private Hot Tub *Separate Entrance *Private Parking *King Bed, Tuft & Needle Mattress *Large Garden *Kitchenette with Full-size Fridge and Cooking Supplies (No oven) *Gas BBQ *Good Location *Garden Hammock in good weather LGBTQ Friendly, All Races Welcome. We celebrate diversity and welcome all loving hearts, regardless of gender or race. Portland Permitted Property

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
4.91 out of 5 average rating, 105 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 spacious living area features light green walls and hardwood flooring. A gray sofa and a blue accent chair offer comfortable seating, complemented by a wooden coffee table. The open kitchen is visible in the background, showcasing modern appliances and warm wood cabinetry.
Guest house in Milwaukie
4.98 out of 5 average rating, 364 reviews

River Forest Guest House, River and Dock access

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

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, 739 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, 271 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.

Popular amenities for Oswego Lake holiday rentals

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