Waterfront holiday rentals in Lake Oswego

Dream Cottage! Springwater Bike/Walking Path!

Explore, recharge, dream in your own quiet & inspiring country-in-the-city cottage. Sellwood is a great riverside neighborhood, featured in Sunset’s Best Places to Live in the West. Set off on a bike path adventure or start your novel at the writer’s desk. Walk to coffee shops, restaurants & New Seasons Market grocery. Ideal for College visits: drive times, 10 min to Reed, 10 min to Lewis & Clark, 15 min to PSU. Note: PLEASE ASK about weekly or monthly discounts if you're planning extended stay!

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

Gorgeous Lake Front Home, Central Location

Luxurious 3 Bedroom 2.5 Bath home. Gourmet Kitchen; brand new upscale furnishings/artwork. This private, lake-front 2 story end unit with balcony views is in a convenient, central location. You will enjoy the vibrancy of an urban environment; yet still be close to nature. The lake is surrounded by tree lined, brick paved walking paths leading to local eateries, shops and public parks all within walking distance. Approximately 25 additional Restaurants; located within short driving distances!

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!!

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

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

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.

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

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.

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!

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.