Holiday houses in Oswego Lake

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Top-rated holiday rentals in Oswego Lake

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Top Guest favourite
French doors open to a private patio area, revealing outdoor seating under a vibrant green umbrella. A variety of plants and flowers decorate the space, enhancing the inviting atmosphere. A stainless steel refrigerator is positioned nearby, adding functionality to the kitchen setting.
Guesthouse in Portland
4.99 out of 5 average rating, 139 reviews

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.

Top Guest favourite
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 Oregon City
4.97 out of 5 average rating, 250 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!!

Guest favourite
A spacious living area is furnished with two green sofas and a round coffee table atop a geometric-patterned rug. Natural light filters through the large window, illuminating the room's neutral walls and warm wooden flooring.
Apartment in Portland
4.87 out of 5 average rating, 124 reviews

Well-equipped Cozy & Chic 2 bedrooms Apartment

Welcome to this newly remodeled cozy and chic two bedrooms, one bath Fourplex apartment with balcony to unwind and enjoy Oregon’s fresh air. Interiors have been tastefully designed and thoughtfully equipped to offer comfort and convenience for visitor from near and far to ensure it feels like home while traveling. Close to 99W (Pacific Highway), 217 freeway and major groceries stores. For those who love shopping and enjoy Oregon's Free-Sales-Tax, Washington Square Mall is only 5 minutes away.

Top Guest favourite
The kitchen features white cabinetry and a modern countertop with a sink. A coffee maker and tea kettle are visible. Natural light fills the space through nearby windows. A cozy living area can be seen in the background, adding warmth to the environment.
Guesthouse in Lake Oswego
4.97 out of 5 average rating, 122 reviews

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.

Top Guest favourite
The exterior of a modern guest house features a unique sloped roof and large glass doors that open to a patio. A firepit is surrounded by four black wire chairs, and a mix of trees and fencing provides privacy to the space.
Guesthouse in Portland
4.93 out of 5 average rating, 422 reviews

Dwell | Upscale Woodstock Retreat | Walk to Dining

Now Net Zero Energy! Dwell has 18 solar panels that cover more electricity that the building uses! New modern House with gourmet kitchen. Enjoy the tile shower with endless hot water, smart tv, and cozy furniture. Short walk to Woodstock village with Double Mountain Brewing, New Seasons. Easy access to public transportation, or sit back and relax on the patio with firepit. Light and bright guest house and you have the place to yourself. There is a fenced yard that is pretty private.

Guest favourite
A charming blue cottage is framed by a welcoming front porch with wooden railings. Lush green plants and purple flowers decorate the landscape. An American flag is displayed on the railing, and a car is parked in the driveway alongside the property.
Bungalow in Gladstone
4.91 out of 5 average rating, 187 reviews

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.

Top Guest favourite
A lush green yard is framed by trees, featuring a cozy yurt and stone pathway. Colorful flower pots overflow with blossoms, while seating areas with chairs and a small table invite relaxation. A play structure and well-maintained garden add to the inviting atmosphere.
Yurt in Portland
4.99 out of 5 average rating, 1,480 reviews

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.

Guest favourite
An architectural micro home is nestled among lush greenery, surrounded by trees. A wooden exterior enhances the natural setting. The structure features a small side porch and multiple large windows, allowing light to flood the interior. A pathway made of stones leads to the entrance.
Guesthouse in Portland
4.84 out of 5 average rating, 162 reviews

The Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

Top Guest favourite
A charming guesthouse is nestled within a lush garden, surrounded by colorful flowering bushes and sculpted hedges. The structure features large windows that offer a glimpse of the serene interior. The path leading to the guesthouse is intertwined with greenery, enhancing the tranquil atmosphere.
Cottage in Portland
4.92 out of 5 average rating, 456 reviews

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.

Top Guest favourite
A compact patio area is visible, featuring a bistro table and two black chairs. The entrance to the apartment is framed by large windows, showcasing a hint of the interior. A bright red door adds a welcoming touch to the exterior.
Guesthouse in Portland
4.99 out of 5 average rating, 257 reviews

Pure Privacy for 2 in Multnomah Village

Secluded but welcoming, smoke-free, private-entrance, 1-bedroom apartment for 2 people. The apartment is within 3 blocks of historic and unique Multnomah Village. Access to shopping, restaurants, quick freeway access to downtown Portland (approximately 10 minutes), and close proximity to 2 community centers with work-out facilities. The apartment is also within 1.5 hours of beaches, wineries and the mountains if you seek activities that are a bit farther away.

Top Guest favourite
A hot tub is situated on a deck, surrounded by serene views of rolling hills at dusk. String lights hang gently above, providing soft illumination. Green glow from the hot tub reflects off the water, creating a calming atmosphere as twilight descends.
Tiny home in Estacada
4.99 out of 5 average rating, 100 reviews

Luxury Tiny Home with a view!

Escape to peace and tranquility at Tiny Timber, a cozy retreat set on a scenic 65-acre Christmas tree and timber farm. Take in sweeping Cascade views, unwind with luxurious amenities, and enjoy your own private oasis. Start or end your day with a soak in the private hot tub under the open sky. Ideally located near the Clackamas River, Mt. Hood National Forest, and greater Portland, Tiny Timber is your gateway to adventure, exploration, and true relaxation.

Top Guest favourite
A modern kitchenette features sleek white cabinetry and a granite countertop with bar seating. Stainless steel appliances, including a microwave and coffee maker, are visible. Soft lighting from pendant lights and a lamp creates a warm ambiance. A decorative bowl rests on the counter.
Guest suite in West Linn
5 out of 5 average rating, 258 reviews

Arbor Suite Apt - Washer/Dryer, Desk, Free Parking

There is a private entrance to this 725 sq ft. bright, CLEAN, and SANITIZED guest apartment within a home, in a well established neighborhood on the border of West Linn and Lake Oswego. Spacious, beautifully furnished one bedroom with an office/den (includes fiber optic internet & monitor ) in a quiet and desirable suburb of Portland that offers a lush treed garden with a gas fire pit and patio. YouTube TV available. Close to Mary's Woods!

Popular amenities for Oswego Lake holiday rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Clackamas County
  5. Lake Oswego
  6. Oswego Lake