Vacation rentals in Oswego Lake

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Top-rated vacation rentals in Oswego Lake

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Top guest favorite

An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.

Guesthouse in West Linn

4.96 out of 5 average rating, 148 reviews

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

Guest favorite

A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.

Home in Portland

4.96 out of 5 average rating, 117 reviews

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.

Guest favorite

A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.

Guesthouse in Portland

4.96 out of 5 average rating, 112 reviews

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

Guest favorite

A tree-lined pathway leads to a wooden staircase bordered by blooming flowers. The pathway features a gentle slope with a railing, guiding visitors toward a secluded entrance nestled among greenery. Lush foliage and vibrant blooms provide a natural, tranquil setting.

Guesthouse in Lake Oswego

4.95 out of 5 average rating, 381 reviews

Cozy and Charming

The studio unit has a queen size bed equipped with full kitchen and bathroom as well as working area with wifi and HBO, Showtime. It has separate entrance and located at secluded hilly area. There are 8-9 steps to the unit and maybe difficult for some guests. Washer/dryer are in the house, guests can let us know if they like to use. During a winter snow/ice storm, our location can be challenging. You may need to cancel or change your reservation accordingly if there are snow/ice storm.

Top guest favorite

The entrance features a welcoming design with a small bicycle parked beside a potted plant. A doormat with the word 'WELCOME' is placed at the threshold, leading into a bright and inviting interior visible through the open door.

Home in Lake Oswego

4.93 out of 5 average rating, 125 reviews

#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.

Top guest favorite

The exterior of the Pheasant Hill Carriage House is showcased, featuring a stone and shingle facade with a welcoming porch. Lush flower beds display vibrant blooms, and an American flag is proudly displayed. Large windows invite natural light, enhancing the charming entrance.

Apartment in Lake Oswego

5 out of 5 average rating, 102 reviews

Pheasant Hill Carriage House

Pheasant Hill Carriage House has been described by guests as " Better than a five-star hotel -- you won't want to leave." We provide the best in hospitality, the amenities of home in a beautiful park-like setting, and a relaxing night's sleep in a premium king-sized bed, . Great for an extended business trip or a romantic getaway. Private entrance, high-speed Wi-Fi, central air, professional quality exercise equipment, full-sized kitchen, full-sized washer and dryer.

Top guest favorite

A comfortable sleeping area is featured, with a queen bed dressed in neutral bedding and accented by a blue throw pillow. Two bedside lamps provide soft lighting, and a dresser stands beside the bed. Natural light enters through a nearby window, with curtains partially drawn.

Cottage in Lake Oswego

4.94 out of 5 average rating, 306 reviews

Peacock Grove Cottage in Lake Oswego, OR

Sunny, private one bedroom cottage in quiet, wooded neighborhood. Separate dwelling behind main house. Queen bed, sofa bed, TV, WiFi, A/C, full kitchen, washer & dryer, bathroom with shower and beautiful patio. One mile from I-5 and 8 miles to downtown Portland. Short drive to downtown Lake Oswego. Walking distance, just two blocks, to La Provence, Jefe, Zupans, Albertsons, Starbucks, Waluga Park. Perfect for families or the business traveler. Come stay!

Guest favorite

The exterior of a charming white house is visible, featuring a sloped roof and large front windows. Two black chairs are positioned on the porch, surrounded by a lush green lawn and mature trees, creating a serene outdoor setting.

Home in Lake Oswego

4.89 out of 5 average rating, 176 reviews

“Sucker Creek Inn” - with partial lake view

This home is in a great location only a 10 minute walk to downtown Lake Oswego where you'll find a wide variety of restaurants, bars, and shopping. It's also just a five minute walk from the Willamette River, so bring your kayaks and SUPs to explore all that Lake Oswego has to offer, or take a short Uber ride (10 minutes) into downtown Portland. Lastly, the lot is next to one of the oldest homes in Lake Oswego- built when Lake Oswego was known as Sucker Creek

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, 714 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 compact kitchen area features a farmhouse sink with a decorative faucet and a wooden countertop. Shelves hold glassware and dishware, while a coffee maker and other appliances are neatly arranged. Soft lighting creates a welcoming environment for meal preparation.

Guest suite in Lake Oswego

4.93 out of 5 average rating, 690 reviews

The Hen Den

Light filled and cozy 600 sf private guest suite with private entry in a private garden setting. Grill up a burger or head down to the local French restaurant for some tasty food. Rent gear at the REI down the road and head to Mt. Hood for an adventure. Close to Bridgeport Mall and amazing restaurants with easy access to I-5, I-205 and I-117 to head to the coast, the Columbia River Gorge or downtown Portland.

Guest favorite

A mesmerizing mirrored room features a thick tatami mat rolled out for sleeping. Soft ambient lighting highlights the infinite reflections, creating a whimsical atmosphere. The bedding is neatly arranged, inviting guests to experience a truly unique and immersive stay.

Home in Lake Oswego

4.97 out of 5 average rating, 218 reviews

Signal House – Light Up The Portal

Signal House is an immersive art home from The Book of Houses in Pudding Heroes – a living chapter of the story. It is an overnight experiential stay, for travelers looking to jump off to the next dimension. Our 3 room home's highlight is the fully mirrored experience with sound /mood lighting for play & sleep. We have a cat meme lounging experience in the media room. 15 minutes from Portland on I-5.

Top guest favorite

A cottage with light yellow siding is nestled among greenery, featuring two windows adorned with flower boxes. A stone pathway leads to the entrance, flanked by ferns and a decorative stone lantern. Lush trees provide a serene backdrop.

Guesthouse in Portland

4.96 out of 5 average rating, 674 reviews

Portland Cottage with Kitchenette

Our cottage is in a quiet southwest Portland neighborhood. It includes a pillow top queen size bed, microwave, refrigerator, Keurig coffee maker, toaster oven, 2 burner hotplate, hair dryer, soap & shampoo. Easy access to I-5 and downtown Portland by car or public transportation.