Vacation rentals in Oswego Lake

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Top-rated vacation rentals in Oswego Lake

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

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Guest favorite
Treehouse in Portland
4.82 out of 5 average rating, 536 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 favorite
A spacious living area is adorned with natural stone flooring and features a grand piano. French doors open to the outdoor space, allowing for natural light. A plush couch, a wooden table, and a stylish armchair provide comfortable seating, accompanied by a decorative area rug.
Home in Lake Oswego
4.94 out of 5 average rating, 66 reviews

Beautiful Italian-style Villa in Lake Oswego

Beautiful private 1907 Italian-style villa in Lake Oswego w 100' trees. Views of the lake. Private. Gourmet kitchen. Ingredients for cooking There are 3 bedrooms: - Room 1 has a queen-sized bed - Room 2 has 2 twin beds. - Room 3 has a double bed Please see the last image in the listing for details on how the bedrooms are arranged Large stone patio for outdoor dining All the construction in the neighborhood is finished, and we have a perfect new road! Lots of room for your get-together.

Top guest favorite
A charming outdoor area is visible, featuring a stone pathway leading to a cozy seating arrangement with two black chairs. The bungalow is framed by lush greenery, with warm light emanating from the windows, inviting a peaceful ambiance.
Home in Southwest Portland
4.97 out of 5 average rating, 173 reviews

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

Guest favorite
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, 113 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.

Guest favorite
A modern kitchen is highlighted by sleek cabinetry and stainless steel appliances. A spacious island with seating invites gatherings while abundant natural light streams through large windows, illuminating the counters. A dining set completes the area, offering a comfortable space for meals.
Home in Tualatin
4.85 out of 5 average rating, 272 reviews

Charming Urban Farm House - 24 hour self check in

This charming 2 story house that is a full time Airbnb home and has 5 bedrooms and was recently remodeled and resembles the charm of the tv show fixer upper. Huge yard, new hardwoods, remodeled kitchen, comfortable furniture and close to everything. 20 min to downtown. This house is a full time Airbnb listing, has super fast internet/wifi, has a Samsung SmartTV and is close to everything. 24hour self check in and check out. Tons of parking.

Top guest favorite
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.
Guesthouse in Milwaukie
4.98 out of 5 average rating, 373 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 favorite
A single-story house with a welcoming front porch is surrounded by a lush, green lawn. The exterior features a mix of white siding and dark roofing, with two garage doors on one side. Tall trees provide a natural backdrop, enhancing the tranquil setting.
Home in Lake Oswego
4.96 out of 5 average rating, 159 reviews

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. The master has a king bed, the other two have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets & TVs, there is a desk and chair for a work space if needed in garage. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Top guest favorite
Home in Lake Oswego
4.98 out of 5 average rating, 49 reviews

The Walking Woods Retreat in Lake Oswego

Escape to Lake Oswego in this beautifully remodeled 3-bed, 2.5-bath home blending Northwest charm with modern updates. Vaulted ceilings and clerestory windows fill the space with natural light. A private top-floor master retreat offers seclusion, while the lower level includes two bedrooms, a cozy family room, and full bath. Nestled on a wooded corner lot, enjoy serene privacy and nature. Relax on 3 patios with outdoor dining.

Top guest favorite
Home in Lake Oswego
4.97 out of 5 average rating, 102 reviews

Luxury Lake Oswego Retreat - all new & great patio

Luxury Lake Oswego retreat just 3 blocks from George Rogers Park and New Seasons Market. This exceptional custom home, valued at over $1.2M, features 3 bedrooms (2 king, 1 queen), all-new upscale furnishings, a gourmet kitchen with a Jura E6 espresso machine, cozy gas fireplace, and a huge covered patio with a firepit, outdoor TV, and comfortable seating. Perfect for families seeking comfort, style, and an ideal location

Top guest favorite
A spacious studio layout is highlighted, featuring a large bed with a cozy throw. A modern kitchenette is visible in the background, along with a dining table and chairs. A wall-mounted TV offers entertainment options, and natural light fills the room.
Apartment in Lake Oswego
5.0 out of 5 average rating, 24 reviews

Entire Rental Unit Ground Level Lake Oswego, OR

Welcome to comfort and convenience in our new ground level studio, centrally located near a variety of restaurants, coffee shops, and grocery stores. This unit is the most spacious out of our three and is ideal for solo adventurers or couples. Enjoy easy freeway access, proximity to Bridgeport Village, a 4K SmartTV for streaming, high-speed internet, kitchenette and laundry. Perfect for both relaxation and exploration!

Top guest favorite
A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.
Home in Southwest Portland
4.96 out of 5 average rating, 164 reviews

Portland Modern

Welcome to our Midcentury Modern, a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. License number is 26ASTR-REN-00301

Top guest favorite
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, 755 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.

Popular amenities for Oswego Lake vacation rentals