
Holiday houses in Oswego Lake
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Top-rated holiday rentals in Oswego Lake
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Rose City Park Retreat
Located in beautiful Rose City Park, our studio is built with our guests in mind. It is clean and bright with 16 ft vaulted ceilings and skylights. Every detail has been thought of to make this a comfortable and inviting experience while you explore all that Portland has to offer. Beautifully tiled shower. Bamboo sheets and plush down pillows. You are within walking distance of restaurants, parks, bars, and food carts along with public transportation. We are close to downtown and PDX airport.

Luxurious Riverfront GuestHouse, Sauna & HotTub.
Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

#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.

Crossroads Country Cottage
Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

The Wee Humble Cottage
Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

A Cute, Clean, & Comfy SW Portland Guest Apartment
Jasper House is a very clean, pet friendly one bedroom "in-law" apartment in Garden Home. Located on a quiet Culdesaq. Easy access to 217 and I-5. The perfect West side location, close to everything. Great for business and pleasure travelers a like! No additional pet fees for up to 3 pets! This 450 sq ft apartment has a private deck, cozy sitting room w/double futon, 40" TV w/Roku, dining table & kitchenette. The bedroom has a comfy King bed & vanity/desk. We have A/C as well!

Garden Home Backyard Yurt Experience
Our cozy-comfy 4 season yurt is nestled under majestic trees on a beautifully landscaped 1/3 acre. Located in a quiet, safe SW Portland neighborhood with a park, hike/bike trail a block away. We are 6 miles from downtown, with beaches, gorge and Mt. Hood accessible for day outings. There is a full kitchen, a natural gas fireplace and complete electrical and plumbing service. The guests full bathroom is located in the home's utility room a short lighted pathway walk from the yurt.

Multnomah Hidden Pond - stunning upscale romantic!
Our B&B is an *experience* and not just a place to spend the night. Situated in the coveted neighborhood of Multnomah Village, this is a super romantic garden cottage style gem. Here, you will feel like royalty sleeping in the carved mahogany four-poster QUEEN SIZE bed, embraced by an amazing mattress, and surrounded by designer bed colors, prints and toss pillows. You will find a gorgeous, top-notch tiled bathroom, a modern beautiful kitchen and many delightful surprises..

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.

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.

Light Filled Garden Studio
Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

South Portland Luxury Condo, City & Mountain Views
Discover our South Portland penthouse condo, where luxury meets comfort. Enjoy views of the city skyline and distant mountain views from this bright, 1350 sq ft space. Perfect for leisure or work, our condo offers a spacious bedroom, office, and top amenities in a secure, family-friendly area. Steps away from shopping, dining, and transport, with secure parking included. Experience the best of Portland in style!
Popular amenities for Oswego Lake holiday rentals
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- Moda Center
- Silver Falls State Park
- Timberline Lodge
- Laurelhurst Park
- Mt. Hood Skibowl
- Oregon Zoo
- Providence Park
- Enchanted Forest
- The Grotto
- Portland Japanese Garden
- Beacon Rock State Park
- Wonder Ballroom
- Wings & Waves Waterpark
- Powell's City of Books
- Hoyt Arboretum
- Tom McCall Waterfront Park
- Oaks Amusement Park
- Arlene Schnitzer Concert Hall
- Portland Art Museum
- Evergreen Aviation & Space Museum
- Pittock Mansion
- Reed College
- Tryon Creek State Natural Area
- Council Crest Park




