Holiday rentals with a fireplace in Lake Oswego

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 completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

Beautiful townhome on bike trail with river views

Welcome to Miles Street, a unique 2200 sq ft bright and airy 2 bedroom 4 story townhome on Portland's 26 mi riverfront trail with Willamette river views. An entertainer's dream with open concept 4th floor kitchen, dining and living room with fireplace, balcony, and river views. Two 3rd floor bedrooms including master with fireplace and balcony, & bathroom with heated floors, open shower & soaking tub. 5th floor rooftop deck has gas grill & firepit table with view of the Willamette and Mt. Hood.

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!!

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

Sherwood Hollow- Senior discount (60+) $88/night

Welcome to Sherwood Hollow! This completely refurbished retreat is a large 1200 square foot downstairs suite in our 1960's home. This spacious area has a large living room, eat-in kitchen, and spacious bedroom. The unit is private and completely closed off from the upstairs. Our home is located just a short walk from Old Town Sherwood and beautiful Stella Olsen park. This unit is near the bottom of a hill, a bit of a climb coming up from Old Town, and the driveway is on an incline.

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.

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. 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. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

Secret Garden Guesthouse!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

Newly Built Guesthouse with Private Courtyard

Newly built one-bedroom guesthouse with charming private backyard in the popular Maplewood neighborhood. Light-filled, open floor plan with vaulted ceilings. Walk to Maplewood Coffee & Tea. Located 1 ½ miles from Multnomah Village, 3-4 miles from downtown Portland, Lewis & Clark College and OHSU, 7 miles from Nike. Easy day trips to the Oregon Coast, Columbia River Gorge, Mt Hood, and Yamhill County’s Wine Country. ASTR Permit #18-220704-HO

Lovely Loft Apartment

Spend a night in our spacious and bright loft apartment. Enjoy the unique and homey interior, or take a walk around our 1.5 acre property. Perhaps even enjoy a cup of wine on our deck by a fire. If you're interested in getting out, we are only a 20 minute drive from Portland and at the center of many other attractions. At the end of the day enjoy the wonderful view of the sunset and settle down in a comfortable king sized bed.

Cottage in the Woods: SANITIZED! FULLY STOCKED!

Cute 500 sq foot cottage behind a main house, located on a 1/2 acre park-like setting lot on a dead end street. Quiet location, easy access to I-5, shopping, Lake Oswego, hiking, and the Tualatin River. The cottage has one bedroom w/ a queen bed, blow up queen mattress, and a large couch. The large fir trees on the property attract many birds and squirrels. We also have a flock of neighborhood peacocks that visit!