House vacation rentals in Lake Oswego

Hidden Garden Cottage

This 850 sf. cottage is a century old but was completely updated 12 years ago with era-appropriate furnishings, giving it a period (and safe) feel. Breakfast goodies, art, books, and a woodstove make it cozy. It sits on half an acre so lots of room for kids . It's in SW Portland, minutes from downtown. It's quiet, great for working or vacationing. An outdoor fire pit and gardens make it unique. There's even a zip line for kids. Family gatherings also fine. (Note: There is a $60 fee per dog.)

Charming home on private street with hot tub

Keep it simple at this conveniently situated retreat, just a 10-minute drive from downtown Portland and moments away from Multnomah Village. Nestled at the end of a private street in a desirable neighborhood, this charming home offers a spacious interior (with recently added centralized A/C) and inviting shared outdoor spaces. Relax and unwind in the hot tub, gather around the barbecue, or enjoy the patio and fireplace. Remote worker? Come be productive in our sitting/standing desk station.

#StayInMyDistrict Lake Oswego Honey Bee Cottage

#StayinMyDistrict Lake Oswego Honey Bee Cottage. Live like a local while experiencing the trendy Lake Oswego District! 5 blks to coffee shops, restaurants, shopping & local hot spots! Convenient to West Linn, SW Portland & Tigard Neighborhoods. Private Cottage nestled in the trees, and furnished to create a comfortable and charming space! Historic 1 bed/1bath (+sofa bed & Futon) King Suite, Kitchen, W/D, Private Patio & Fenced Yard. FREE Parking. Pre-Approved Dogs w/addt’l $50 per pet fee.

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Spacious and serene. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Please note that owners live on site as required by Portland laws. Located in a quiet neighborhood, close to hiking trails. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland

Quaint Garden Cottage

This garden charmer is the perfect place to call your home away from home and has room for the whole family! Featuring central heat and AC, 2 bedrooms w/Queen beds & closets, couch with pull-out bed, 50in Smart TV, free wifi, bathroom with shower and full sized bathtub, kitchen with gas stovetop/oven, dishwasher, and Keurig coffee maker, dining room, your own washer and dryer, onsite parking, charming front porch and back deck, and secret garden backyard all make this a must-stay spot!

Chateau Lesieutre atop Dundee Hills’ Highest Point

Wake up above the Willamette Valley, surrounded by Oregon’s most celebrated wineries. Located at the highest point in Dundee, this serene retreat offers exquisite views. Sip your morning coffee on the terrace, enjoying the fresh country air and feeling as though you’re floating above the hills. With more than 10 wineries within two miles, it’s an ideal base for exploring wine country. After a day out, return home to unwind with evening stargazing in the courtyard or on the terrace.

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.

Live Like a Local in Artful Craftsman by Division

Beautiful 1916 Portland bungalow - bursting with character, original woodwork & striking local artwork. Located on a quiet residential street, it is steps away from the bustling Division/Clinton corridor filled with restaurants, shops, and bars!. Easy street parking surrounds the whole house in this charming, tree-lined neighborhood. From the covered front porch to the charming backyard, and everything in between- spread out and enjoy all Portland has to offer!

“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

Central Cozy Modern 3Bd Oasis

Centrally located in West Linn. Safe, Clean, Great for Families! Minutes from Award Winning Wineries, Lake Oswego, Oregon City, and Downtown! This home is minutes walk North Willamette Park! Stylish, comfortable, and clean with all the amenities you need to make your vacation or business trip a success. Property is a unit in a newly renovated duplex. Enjoy the private fenced back yard and patio / common yard with picnic tables / Free private parking!

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.

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.