Vacation rentals in Lake Oswego

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Top-rated vacation rentals in Lake Oswego

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

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Top guest favorite
Guesthouse in Southwest Portland
5 out of 5 average rating, 161 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.

Top guest favorite
Guesthouse in West Linn
4.97 out of 5 average rating, 172 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.

Top guest favorite
A stunning log home is surrounded by lush greenery and features an expansive front porch with large windows that allow natural light inside. The property is well maintained, showcasing a driveway bordered by manicured lawns and mature trees, providing a welcoming entrance.
Home in West Linn
5 out of 5 average rating, 109 reviews

Knotty Pine - Log Home

Located in the heart of historic Willamette district in West Linn is a beautiful log home situated on 1.3 acres. Short walk to Willamette park (next to the river), walk to shops & restaurants. Private entrance, easy parking. Apartment is on one level, no stairs (800 square feet). Living room, full size kitchen and two bedrooms. Master- king size bed and Guest room - double bed, no closet. Includes a laundry room . Great for extended stay. Close to I-205, 25 min. to PDX and downtown Portland.

Top guest favorite
Guesthouse in Southwest Portland
4.96 out of 5 average rating, 410 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.

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
4.9 out of 5 average rating, 151 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 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, 125 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 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, 108 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
Guest suite in Lake Oswego
4.94 out of 5 average rating, 296 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.

Top guest favorite
The exterior of the guesthouse is framed by vibrant gardens, featuring blooming roses and lush greenery. A winding path leads to the entry, surrounded by neatly trimmed hedges. Colorful flowering bushes add to the serene, natural setting, creating a welcoming environment.
Cottage in Portland
4.92 out of 5 average rating, 466 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.

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
4.88 out of 5 average rating, 194 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

Top guest favorite
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.
Home in Lake Oswego
4.96 out of 5 average rating, 149 reviews

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. The master has a king bed, the other two have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets & TVs, there is a desk and chair for a work space if needed in garage. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Superhost
A gravel pathway leads to a charming gray cottage nestled among tall trees. The setting features a pair of wooden chairs positioned outside, inviting relaxation in the peaceful surroundings. Sunlight filters through the foliage, highlighting the natural beauty of the site.
Guesthouse in Lake Oswego
4.83 out of 5 average rating, 212 reviews

Cottage in the Woods: SANITIZED! FULLY STOCKED!

Cute 500 sq foot cottage behind a main house, located on a 1/2 acre park-like setting lot on a dead end street. Quiet location, easy access to I-5, shopping, Lake Oswego, hiking, and the Tualatin River. The cottage has one bedroom w/ a queen bed, blow up queen mattress, and a large couch. The large fir trees on the property attract many birds and squirrels. We also have a flock of neighborhood peacocks that visit!

Popular amenities for Lake Oswego vacation rentals

When is the best time to visit Lake Oswego?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,374 GYDG$31,374 GYDG$30,328 GYDG$27,191 GYDG$30,328 GYDG$28,446 GYDG$31,374 GYDG$31,374 GYDG$30,328 GYDG$33,047 GYDG$34,930 GYDG$34,511 GYD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Lake Oswego?

    Many visitors choose accommodations near the downtown arts district or close to the waterfront, where cafés and shopping are easily accessible. Residential areas around community parks are also popular for quieter stays.

  • What are the best things to do in Lake Oswego with kids?

    Children often enjoy play areas in local parks, lakeside picnics, or exploring community gardens. The Lake Oswego Public Library regularly hosts family activities and story times.

  • How is the weather in Lake Oswego?

    Lake Oswego experiences cool, rainy winters around 36-47°F (2-9°C) and warm, drier summers near 82°F (28°C). Packing a rain jacket or umbrella is practical for the wetter months, while summer calls for lighter layers.

  • When is the best time to visit Lake Oswego?

    Late spring through early fall is often recommended, with milder temperatures, blooming gardens, and community events. The drier months bring more chances to enjoy lakeside walks and outdoor gatherings.

  • What are the best places to visit in Lake Oswego?

    Explore Millennium Plaza Park for community events and views of the lake, visit the Lake Oswego Public Library, or enjoy exhibitions at the Arts Council of Lake Oswego. The downtown area is popular for boutique shops and local eats.

  • What are some hiking trails in Lake Oswego?

    Try exploring Tryon Creek State Natural Area, which has wooded trails, or follow paths in local parks around the lake. Some trails are suitable for all ages and connect with peaceful green spaces.

  • What are some family activities we can do in Lake Oswego?

    Families can explore walking trails, take part in workshops at cultural centers, or enjoy seasonal events. Parks often feature playgrounds and open lawns suitable for games or picnics.

  • What are some of the best day trip ideas from Lake Oswego?

    Visitors frequently explore nearby wineries, scenic hiking areas, or neighboring arts districts with galleries and cafes. The surrounding Willamette Valley is known for nature spots and seasonal farm events.

  • Are there any pet friendly accommodations available in Lake Oswego?

    Many Lake Oswego hosts welcome guests traveling with pets, particularly in areas near parks and walking trails. It is helpful to check individual listings for specific details on pet amenities and guidelines.

  • What are some local tips for visiting Lake Oswego?

    Arrive early if you plan to visit popular parks or farmers’ markets, especially during weekends or community events. Locals enjoy morning walks by the lake and recommend exploring independent cafés for pastries and coffee.

  • What is Lake Oswego known for?

    Lake Oswego is known for its scenic namesake lake, vibrant arts community, and tree-lined neighborhoods. Locals value outdoor recreation, frequent farmers’ markets, and year-round cultural events.

  • What are the best hidden gems to explore in Lake Oswego?

    Explore local art galleries, peaceful nature preserves, and community parks tucked around the lake. Try following art walks or visiting neighborhood gardens, which are frequently suggested by residents.

  • What are the best foods to try in Lake Oswego?

    Lake Oswego’s dining scene features Pacific Northwest ingredients—expect salmon, locally sourced berries, and artisan cheeses. Bakeries and cafés around town are known for pastries and regional coffee.

  • What should I bring for a trip to Lake Oswego?

    Bring weather-appropriate clothing, such as a light rain jacket for cooler months and comfortable walking shoes for outdoor activities. Lighter layers work well for summer visits, and a reusable water bottle is helpful for exploring local parks.

  • What is the nightlife in Lake Oswego like?

    Lake Oswego's nightlife centers around cozy wine bars, lounges, and restaurants that host live music on weekends. Evenings tend to be relaxed, with opportunities for socializing over local food and drinks.

  • What are the most popular events or festivals in Lake Oswego?

    Lake Oswego hosts art festivals in summer, family events during the winter holiday season, and outdoor concerts in parks throughout warmer months. Farmers’ markets draw both locals and visitors with regional produce and music.

  • Are there family friendly vacation rentals in Lake Oswego?

    Lake Oswego has many vacation rentals suitable for families, including homes with kitchens, multiple bedrooms, and access to parks or lakefront areas. Neighborhoods with nearby green spaces are frequently suggested for guests with children.

  • Are there vacation rentals with a dedicated workspace in Lake Oswego?

    Yes! Work meets play with ease at over 130 vacation rentals in Lake Oswego featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in Lake Oswego

  • Total vacation rentals

    Explore 220 vacation rentals in Lake Oswego

  • Nightly prices starting at

    Lake Oswego vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 14,090 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Lake Oswego vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Lake Oswego stays are highly rated by guests—averaging 4.9 out of 5!

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