Waterfront vacation rentals in Lake Oswego

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Top-rated waterfront rentals in Lake Oswego

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of the cottage is showcased, featuring a bright orange facade and white trim. Two windows are visible on the side, with a glass door that leads to the patio. Surrounding greenery includes tall grasses and various plants, contributing to a natural setting.
Guesthouse in Westmoreland
4.97 out of 5 average rating, 606 reviews

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!

Top guest favorite
A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.
Guest suite in Milwaukie
4.95 out of 5 average rating, 436 reviews

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.

Top guest favorite
A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.
Guesthouse in Clackamas
4.97 out of 5 average rating, 224 reviews

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!!

Top guest favorite
A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.
Guest suite in Milwaukie
4.96 out of 5 average rating, 182 reviews

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.

Guest favorite
A serene river view is visible, framed by lush trees and greenery. The clear water reflects the sky, while a gentle wake from a boat creates ripples. A sandy beach area is located in the foreground, alongside a manicured lawn and a fire pit.
Guesthouse in Milwaukie
4.88 out of 5 average rating, 183 reviews

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.

Guest favorite
A cozy outdoor deck area is furnished with a glass-top table and two chairs. Lush green grass and trees are visible in the background, along with a serene stream that meanders through the landscape.
Home in Portland
4.87 out of 5 average rating, 683 reviews

A River (stream) Runs Through It

Okay, well, it's a stream, but it's all yours to enjoy. For the nature lovers we have deer, beavers, ducks, nutria, fish, etc. (think wetlands). For everyone, the house (duplex) is fully equipped with a fireplace, BBQ, hot tub central gas heat and central AC. This is a bright, clean and cozy space to land for folks who love the suburbs (not in the city city but we are close drive to the city center) but want to be surrounded by nature. With ambient noise from the creek and highway.

Guest favorite
A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.
Home in Portland
4.93 out of 5 average rating, 261 reviews

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.

Guest favorite
A dining area features a wooden table with seating for four, complemented by a vibrant abstract painting on the wall. A living space showcases a gray sofa and side tables, with a fireplace and mounted television creating a cozy atmosphere. Natural light filters through the window.
Condo in Portland
4.9 out of 5 average rating, 185 reviews

Stunning Portland Condo | Parking, River & Dining

Explore Portland in style! Our freshly renovated top-floor condo offers 2BR/2BA, breathtaking views, and a private deck. Enjoy the convenience of secured parking, complimentary WiFi, and a fully furnished space ready for your stay, whether it's for a night, a month, or longer. Perfectly situated near OHSU, Lewis & Clark, and major medical centers. Steps away from Zupans Market and Willamette River parks. Ideal for travelers seeking comfort and convenience in a prime location.

Guest favorite
The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.
Cabin in Milwaukie
4.89 out of 5 average rating, 730 reviews

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.

Top guest favorite
A spacious living area features light green walls and hardwood flooring. A gray sofa and a blue accent chair offer comfortable seating, complemented by a wooden coffee table. The open kitchen is visible in the background, showcasing modern appliances and warm wood cabinetry.
Guesthouse in Milwaukie
4.99 out of 5 average rating, 351 reviews

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.

Superhost
Condo in Portland
4.89 out of 5 average rating, 122 reviews

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!

Superhost
Home in Troutdale
4.87 out of 5 average rating, 141 reviews

Luxe Riverfront A-Frame | Hot Tub | Fishing

Discover serenity along the Sandy River in Troutdale, OR. Expansive windows flood this modern cabin with natural light and offer breathtaking views of the glacier-fed river and lush forest. Relax on the spacious deck with a private hot tub, enjoy direct river access, and explore the nearby Columbia River Gorge. Whether unwinding in nature or adventuring on trails, this is your perfect PNW getaway.

Popular amenities for Lake Oswego waterfront rentals

When is the best time to visit Lake Oswego?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,956 GYDG$46,090 GYDG$38,165 GYDG$40,459 GYDG$42,753 GYDG$41,710 GYDG$41,710 GYDG$41,710 GYDG$39,416 GYDG$37,122 GYDG$39,833 GYDG$41,293 GYD
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Quick stats about waterfront rentals in Lake Oswego

  • Total vacation rentals

    Explore 20 vacation rentals in Lake Oswego

  • Nightly prices starting at

    Lake Oswego vacation rentals start at G$8,342 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,650 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Lake Oswego vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lake Oswego rentals

  • 4.8 Average rating

    Lake Oswego stays are highly rated by guests—averaging 4.8 out of 5!

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