Vacation rentals in Lake Oswego

Guesthouse in Lake Oswego

A newly remodeled kitchen features white cabinetry and a patterned backsplash. Stainless steel appliances, including a refrigerator, stove, and microwave, complement the space. A dark mat lies in front of the sink area, enhancing the warm wood flooring.

5 out of 5 average rating, 140 reviews

Oswego Empty Nest

The Oswego Empty Nest is a newly remodeled, cozy, one bedroom unit located in Lake Oswego with a private entrance and 500 sq ft of living space. Prepare your own meals in the beautiful full kitchen. Relax, work or entertain yourself in the living space with a large TV with Roku or rest in the quiet comfortable bedroom with an en suite bathroom. Easy access to restaurants, New Seasons, Columbia Outlet, and hiking trails all within walking distance. Close to downtown and quick airport access.

4.96 out of 5 average rating, 148 reviews

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

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.

Guesthouse in West Portland Park

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.

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.

Home in Beaverton-Hillsboro

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.

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.

A single-story house with a welcoming front porch is surrounded by a lush, green lawn. The exterior features a mix of white siding and dark roofing, with two garage doors on one side. Tall trees provide a natural backdrop, enhancing the tranquil setting.

4.96 out of 5 average rating, 136 reviews

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. All bedrooms have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets, one bedroom has a desk and chair for a work space if needed. There is a yoga space set up in the garage w/ mat and mirrors that you are welcome to use. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Home in Beaverton-Hillsboro

A charming single-level cottage is set on a grassy lawn, framed by vibrant trees. The front porch offers a welcoming entry, while flowering shrubs add color to the landscape. A fence provides privacy, and the home's exterior reflects a warm, inviting character.

4.97 out of 5 average rating, 138 reviews

Maple Cottage - Enchanting, Cozy and Private

Nestled on a quiet treed street in the upscale First Addition neighborhood of Lake Oswego, Maple Cottage is a tastefully decorated single level home waiting for you. Enjoy total privacy! Maple Cottage is cozy and clean. This beautiful 720 sq. ft. private cottage has two bedrooms, one bath, a fully equipped kitchen and a living room where you can relax. Stroll to restaurants, bars, shops, the local movie theater, parks, grocery store and more. First Addition is a walker's paradise.

Apartment in Forest Highlands

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.

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.

Guest suite in Mountain Park

A living area is shown with comfortable seating, featuring a large television mounted on the wall. A dining table is set for four, surrounded by natural wood chairs. Decorative plants and framed artwork add warmth to the inviting space.

4.94 out of 5 average rating, 289 reviews

Peaceful 2 Bdrm Suite 1000 sq ft. Upscale Location

Your home away from home includes your own suite of 2 bedrooms, a beautiful kitchen & living area, & bathroom. The home is in a quiet, safe & friendly neighborhood with scenic hiking trails just out the back door. There are several shopping complexes less than 2 miles away. Amenities include high end linens, HD cable pkg, broadcast networks, Netflix & Amazon Prime. 5 min off of I-5 freeway, approx. 15 min to downtown Portland, 10 min to Lewis & Clark college.

4.92 out of 5 average rating, 436 reviews

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

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.

4.94 out of 5 average rating, 306 reviews

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

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!

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.

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

5 out of 5 average rating, 251 reviews

A serene outdoor space features a patio area with two Adirondack chairs positioned around a stone fire pit. An umbrella provides shade over the seating. Lush greenery surrounds the space, and a lighted petanque court is visible in the background.

Guest suite in West Linn

Arbor Suite Apartment - Washer/Dryer, Desk, A/C!

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!

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Popular amenities for Lake Oswego vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake Oswego fishing vacation rentals

4.95 out of 5 average rating, 427 reviews

Guest suite in Milwaukie

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

4.92 out of 5 average rating, 63 reviews

Guesthouse in West Linn

Luxe Apartment on the Willamette River, Wineries

4.97 out of 5 average rating, 174 reviews

A serene lake view is presented, surrounded by lush greenery and trees. The reflection of the trees is visible on the water's surface. A small shed is seen by the water's edge, and a canoe rests on the shoreline, inviting outdoor activity.

Cottage in Newberg

Oxberg Lake Retreat, lake & farm view in wine ctry

4.96 out of 5 average rating, 157 reviews

The exterior of a red barn-style building is featured, with a prominent white star design above the entrance. Two garage doors and multiple windows allow natural light. A stone pathway leads to a small seating area with two chairs, while a BBQ grill is positioned nearby.

Barn in Brush Prairie

Hockinson Carriage House - You Won't Want to Leave

4.92 out of 5 average rating, 128 reviews

An inviting deck is surrounded by lush greenery, featuring two wooden Adirondack chairs positioned near the entrance of a Lotus Belle Tent. The tent's white fabric blends harmoniously with the natural setting, providing a cozy and secluded atmosphere.

Tent in Oregon City

Stargazing Glamping | Swim | Oasis

4.97 out of 5 average rating, 192 reviews

Guesthouse in Clackamas

Luxurious Riverfront GuestHouse, Sauna & HotTub.

4.99 out of 5 average rating, 78 reviews

An outdoor deck is shown, featuring two lounge chairs positioned with a view of a calm lake. The deck is surrounded by a sleek railing and a tree is visible nearby, with cloudy skies reflecting softly over the water.

Apartment in Vancouver

Upscale Lakefront ADU w/ Access to Pickleball Ct.

4.88 out of 5 average rating, 24 reviews

The image features a serene lakefront setting with boats docked along a wooden deck. Paddleboards rest against the dock, surrounded by lush greenery. The sky is painted in pastel colors, reflecting a calm evening atmosphere over the water, enhancing the peaceful surroundings.

Guesthouse in Lake Grove

{Lake Front Fun} The Little Cottage on West Bay

Lake side house rentals in Lake Oswego

4.92 out of 5 average rating, 76 reviews

A charming two-story home features a welcoming front staircase leading to the entrance. The house showcases a white exterior with contrasting dark trim. Lush greenery and a well-maintained pathway enhance the inviting appearance, while large windows allow natural light to fill the interior.

Home in Camas

Camas Lakehouse With Private Hot Tub

5 out of 5 average rating, 111 reviews

The lodge-style home displays a spacious driveway leading to the entrance, surrounded by lush greenery and tall trees. Natural stones and wooden accents are featured on the facade, creating an inviting and rustic appearance. Ample parking space is visible in front of the house.

Home in Oregon City

Highland Park- secluded lodge near the city.

Superhost

A spacious game room features a billiard table at its center, surrounded by bar stools and a sofa. Large windows allow natural light to fill the area, with a TV mounted on the wall displaying content. A dining table for four is positioned nearby.

Home in Vancouver

4.85 out of 5 average rating, 20 reviews

Salmon Creek Chalet Daylight Basement

4.82 out of 5 average rating, 310 reviews

The tranquil water pond reflects surrounding greenery, with several tall trees lining the shoreline. The home is positioned nearby, highlighted by a yellow indication. A grassy area extends along the water's edge, creating a serene outdoor environment.

Home in Vancouver

Waterview Oasis Cottage in Park-Like Neighborhood

5 out of 5 average rating, 17 reviews

A modern kitchen features dark cabinetry contrasted by light countertops and backsplash. Three windows with diamond-pane accents provide natural light. A central island serves as a workspace, equipped with a sink and modern appliances, including a stove and microwave situated among organized kitchenware.

Home in Troutdale

Sandy River Lodge

A charming single-story home features a well-maintained front yard, highlighted by a mix of grass and flower beds. A paved driveway leads to the attached garage. Surrounding trees provide natural greenery, with a low stone wall bordering the entrance. A white picket fence can be seen in the background.

5 out of 5 average rating, 8 reviews

Lamont off the Lake

4.94 out of 5 average rating, 343 reviews

A spacious living area features a modern green sectional sofa complemented by decorative pillows. A vibrant piece of abstract art adorns the wall. Natural light pours in from large windows, illuminating the open kitchen and dining area visible in the background.

Home in North Tabor

❤️ CLEAN ★ LUXURY OASIS ★ NEAR DOWNTOWN

4.88 out of 5 average rating, 34 reviews

A stone fireplace serves as a focal point in a cozy living area adorned with wooden walls and beams. A light-colored sofa is positioned nearby, accompanied by a decorative rug that adds warmth to the space. Soft lighting enhances the welcoming ambiance.

Home in Estacada

Cozy & quiet creek cabin

Lake Oswego fishing house rentals

An expansive deck showcases comfortable seating overlooking the river. A mix of greenery and trees is visible in the distance, along with a serene waterway. A patio table and chairs are positioned nearby, inviting relaxation and enjoyment of the scenic environment.

Home in Milwaukie

5 out of 5 average rating, 3 reviews

Oak Shore Retreat.Riverfront.Pool Table,Karaoke,AC

The charming craftsman home, situated on a sunny corner lot, features a welcoming front porch with seating. Lush greenery and blooming flowers enhance the exterior. A well-maintained lawn and a tree provide shade, contributing to a peaceful ambiance in the historic Sellwood neighborhood.

Home in Westmoreland

4.66 out of 5 average rating, 38 reviews

2BR Renovated Craftsman by Sellwood Park

A sweeping aerial view captures the serene landscape surrounding a winding river, bordered by lush greenery and patches of trees. Homes are visible along the riverbank, providing a glimpse into a tranquil residential area nestled within nature.

Home in West Linn

By the river in the woods

A bright living space features large windows offering views of the outdoors. Comfortable seating arrangements include a spacious sectional and cozy armchairs. A circular coffee table sits in the center, complemented by natural light streaming through sheer curtains. Decorative plants add a touch of greenery.

Home in Damascus

New place to stay

River Homestead- on Clackamas River

A spacious kitchen and dining area is presented, featuring wood cabinetry and a central dining table surrounded by black chairs. Stainless steel appliances, including a refrigerator and oven, are visible. Soft, neutral tones are complemented by natural light from the window, enhancing the bright ambiance.

Home in Camas

5 out of 5 average rating, 3 reviews

2 bed 2 Bath -Full Kitchen - 1200 sqft-city center

A living room features a dark leather sectional sofa adorned with a green accent pillow. Natural light floods in through a large window, illuminating the space. A wooden TV stand holds a flat-screen TV, while a comfortable rocking chair sits nearby, completing the inviting atmosphere.

Home in Estacada

4.62 out of 5 average rating, 78 reviews

Estacada Home - Near Milo McIver State Park!

A charming blue front door welcomes guests to the light gray house, framed by neatly trimmed hedges and lush green plants. A brick path leads to the entrance, with bright landscaping providing a vibrant setting. A spacious driveway is visible to the right, offering ample parking.

Home in Camas

4.67 out of 5 average rating, 55 reviews

Cozy 3 bed in downtown Camas. Enjoy the gorge!

A bright bedroom features a spacious bed dressed in neutral tones, with several decorative pillows arranged neatly. Natural light enters through multiple windows, and a mirrored wardrobe stands in the corner, reflecting the soft hues of the room.