Family-friendly holiday rentals in Lake Oswego

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.

Indoor spaces · Family · Hiking

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.

Kitchen · Family · Sleep quality

Knotty Pine - Log Home

Located in the heart of historic Willamette district in West Linn is a beautiful log home situated on 1.3 acres. Short walk to Willamette park (next to the river), walk to shops & restaurants. Private entrance, easy parking. Apartment is on one level, no stairs (800 square feet). Living room, full size kitchen and two bedrooms. Master- king size bed and Guest room - double bed, no closet. Includes a laundry room . Great for extended stay. Close to I-205, 25 min. to PDX and downtown Portland.

Indoor spaces · Kitchen · Hospitality

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.

Indoor spaces · Kitchen · Sleep quality

#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.

Kitchen · Indoor spaces · Quiet

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.

Indoor spaces · Kitchen · Hiking

Pheasant Hill Carriage House

Pheasant Hill Carriage House has been described by guests as " Better than a five-star hotel -- you won't want to leave." We provide the best in hospitality, the amenities of home in a beautiful park-like setting, and a relaxing night's sleep in a premium king-sized bed, . Great for an extended business trip or a romantic getaway. Private entrance, high-speed Wi-Fi, central air, professional quality exercise equipment, full-sized kitchen, full-sized washer and dryer.

Indoor spaces · Family · Bathroom

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.

Kitchen · Family · Parking

Peaceful 2 Bdrm Suite 1000 sq ft. Upscale Location

Your home away from home includes your own suite of 2 bedrooms, a beautiful kitchen & living area, & bathroom. The home is in a quiet, safe & friendly neighborhood with scenic hiking trails just out the back door. There are several shopping complexes less than 2 miles away. Amenities include high end linens, HD cable pkg, broadcast networks, Netflix & Amazon Prime. 5 min off of I-5 freeway, approx. 15 min to downtown Portland, 10 min to Lewis & Clark college.

Kitchen · Indoor spaces · Getting around

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! Please be advised that beginning Dec19, 2025, construction has begun on three homes behind our cottage. Work can begin at 7:00AM-7:00PM Mon-Fri., 9:00AM-5:00PM Sat.-Sun. There could be noise during those hours, it's out of our control.

Indoor spaces · Kitchen · Getting around

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!

Kitchen · Family · Walkability

“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

Kitchen · Family · Beach