Lake Oswego Holiday Rentals

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Holiday Rentals in Lake Oswego

Property grounds
#StayInMyDistrict Lake Oswego Honey Bee Cottage
10.0 out of 10, Exceptional, (14)
"This cottage was perfect while visiting family in First Addition. Spacious and bright with many thoughtful touches within the cottage to make your stay comfortable. Would highly recommend!"
The price is NZ$443
includes taxes & fees
19 May - 20 May
#StayInMyDistrict Lake Oswego Honey Bee Cottage
Property entrance
Larkspur Landing Hillsboro - An All-Suite Hotel
3.0 star property
8.2 out of 10, Very good, (1473)
"Other than this being a dated property, it was a lovely place to stay, with a kitchenette, living area, and separate bedroom. It was close to a beautiful park on a local creek, with springtime flowers, squirrels, ducks, and bullfrogs. The staff was helpful."
The price is NZ$191
includes taxes & fees
19 May - 20 May
Larkspur Landing Hillsboro - An All-Suite Hotel
Building design
Inn at Northrup Station
3.0 star property
9.4 out of 10, Exceptional, (1891)
"kitschy"
The price is NZ$298
includes taxes & fees
21 May - 22 May
Inn at Northrup Station
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Exterior
Modern Chateau on private hillside with breathtaking views of the Columbia River
10.0 out of 10, Exceptional, (7)
"It was a beautiful home and the view was amazing. Communication with the owner was easy and responses were helpful and quick. I would recommend this home, and hope to go back sometime."
Modern Chateau on private hillside with breathtaking views of the Columbia River
Interior
World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland
10.0 out of 10, Exceptional, (13)
"As we work hard and play harder, this place was great. We used this house for offsite retreat for a few executives. They were able to hunker down, get work done and play some games. Lots of space to spread out."
World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland
Property grounds
Panoramic Riverside and Lush Forests Views, Pet Friendly, New Décor, Steps Away From Dockside
10.0 out of 10, Exceptional, (32)
"This rental surpassed all our expectations in every way! I’ve stayed in numerous vacation rentals over the years, and this one was by far the best. The setting in the forest and on the Tualatin River was surreal. The attention to detail amazing. The Goat Shed & Zen dens were quite clean & cozy. As 2 older women, we felt very safe staying here. Overall centrally located and a quick drive down the road into West Linn offered several wonderful dining options. Definitely plan on staying here again....
Panoramic Riverside and Lush Forests Views, Pet Friendly, New Décor, Steps Away From Dockside
Terrace/patio
A garden view hideaway in the Irvington neighborhood
9.6 out of 10, Exceptional, (273)
"Very nice, very clean,and very comfortable"
The price is NZ$402
includes taxes & fees
20 May - 21 May
A garden view hideaway in the Irvington neighborhood
2 bedrooms, iron/ironing board, WiFi, bed sheets
MEDITERRANEAN URBAN VILLA
9.8 out of 10, Exceptional, (204)
"We really enjoyed our stay. We wish we had more time to just hang out and walk around the community. Everything in the unit was great ( except the beds). Both beds were extremely firm. For this reason alone i would have second thoughts about staying again. If the beds are replaced with medium soft beds we would stay again. Not a major issue but the parking was full both nights we were there and we had to park on the street. I drive a Ram 2500 Mega Cab so that was a trick to find a place big...
The price is NZ$567
includes taxes & fees
20 May - 21 May
MEDITERRANEAN URBAN VILLA
Fridge, microwave, oven, stovetop
Portland Sanctuary
10.0 out of 10, Exceptional, (40)
"The accommodations were wonderful and it felt like home. We had room to gather together and room to spend alone, as needed. Beds were very comfortable and we slept so well. It was close to all the activities we wanted to experience. Veronica was helpful and willing to make suggestions for our stay. It was our first trip to Portland and i would definitely return to this lovely home for any future trips. I can’t say enough good things about it!"
The price is NZ$414
includes taxes & fees
20 May - 21 May
Portland Sanctuary
Property grounds
Sleek Townhome w/ Patio - Walk to Amazing Restaurants, Breweries, Trails & Shops
9.2 out of 10, Wonderful, (117)
"Spacious & centrally located"
The price is NZ$672
includes taxes & fees
20 May - 21 May
Sleek Townhome w/ Patio - Walk to Amazing Restaurants, Breweries, Trails & Shops
Outdoor dining
Quaint private cottage apt. in highly desireable area, close to everything
10.0 out of 10, Exceptional, (143)
"The apartment was everything we expected. What you see in the pictures is absolutely accurate. The outside garden/side yard was just beautiful! Bob always answered any questions in a timely manner and was available by phone if we needed. The house is located in a wonderful neighborhood. We went for a long weekend and was able to walk to the park. Uber is readily available if you don't rent a car. We highly recommend this apartment and hope to stay here again in the future."
Quaint private cottage apt. in highly desireable area, close to everything
Interior
1 block to Washington Park & short walk to shops, eateries on NW 23rd, Downtown
9.8 out of 10, Exceptional, (226)
"This is a cozy efficiency in very quiet and beautiful neighborhood near the park. Easy walk to park and shops and restaurants on 23rd. Hostess is lovely and all communications with her were prompt and helpful! Would definitely stay here again!"
The price is NZ$391
includes taxes & fees
20 May - 21 May
1 block to Washington Park & short walk to shops, eateries on NW 23rd, Downtown
TV, books, video library
Newly Finished Nob Hill Condo w/ Central Location Perfect for Exploring the City
9.6 out of 10, Exceptional, (84)
"Excellent stay at a comfortable apartment in really nice building. Great place to explore from."
The price is NZ$656
includes taxes & fees
19 May - 20 May
Newly Finished Nob Hill Condo w/ Central Location Perfect for Exploring the City
Exterior
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row
10.0 out of 10, Exceptional, (253)
"Clean apartment and close to everything. Free parking on the street."
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row
Fridge, microwave, oven, stovetop
Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything
9.2 out of 10, Wonderful, (99)
"This property is well appointed and worked perfectly for our family of four. The space is wonderful, the location is great and very walkable. I would highly recommend and would stay again."
The price is NZ$684
includes taxes & fees
19 May - 20 May
Beautiful Space w/ Patio & Central Location - Walk to Absolutely Everything
Exterior
Tiny A-Frame Farm Meadow Retreat minutes from downtown
10.0 out of 10, Exceptional, (1)
"We had a wonderful time. The A frame is super cozy and great for a couples night out. You're in the privacy of the woods and even when it’s raining it’s beautiful. Loved the animals on the property too. They’re adorable."
The price is NZ$300
includes taxes & fees
20 May - 21 May
Tiny A-Frame Farm Meadow Retreat minutes from downtown
Property grounds
Two Rivers Relaxing Retreat
9.8 out of 10, Exceptional, (33)
"The apartment was in the basement of the home. It was clean and well appointed. My only issue is my wife and I are tall...6'3 and 5'10. A shorter person would not have to dodge the support beams...LOL! Other than that and not seeing the cats it was a very comfortable stay."
The price is NZ$365
includes taxes & fees
29 May - 30 May
Two Rivers Relaxing Retreat
Lake
Live the Dream on the Lovely Willamette River
9.4 out of 10, Exceptional, (185)
"We stayed for three nights in May. We really enjoyed the beautiful landscaping and looking out over the Willamette River. The ducks, geese and other birds are numerous. The house had the basic supplies needed for cooking and enjoying our stay. I recommend having the early birds stay in the master bedroom since it shares the space with the kitchen and living room. Access to our events downtown was an easy 10 to 15 min drive along the river. We enjoyed hanging out in the hot tub along the shores...
Live the Dream on the Lovely Willamette River
Fridge, microwave, oven, stovetop
New Condo Offers Great Location, Plenty of Services, Walk Everywhere
9.4 out of 10, Exceptional, (58)
"My son and his wife live in this neighborhood. So many wonderful places to eat. Great grocery store right across the street. The condo is as it looks. Nicely supplied, but as someone else said, only one wine glass? The washing machine does not work. We were there for 3 nights. Slept well. Very quiet. Easy to check in and out. Would stay here again."
The price is NZ$550
includes taxes & fees
29 May - 30 May
New Condo Offers Great Location, Plenty of Services, Walk Everywhere
Exterior
Exquisite Historic Suite Close to Downtown 14-21673
10.0 out of 10, Exceptional, (436)
"The architecture is breathtaking. It was hard to leave this oasis and go do things in Portland. The studio apartment is so cozy quiet. I couldn’t wait to get back to the deck."
The price is NZ$300
includes taxes & fees
20 May - 21 May
Exquisite Historic Suite Close to Downtown 14-21673
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See all available properties in Lake Oswego
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Lake Oswego you may be interested in

Reception
Motel 6 Tigard, OR - Portland South - Lake Oswego
2.0 star property
7.2 out of 10, Good, (1006)
"The parking lot felt unsafe but the staff and room were excellent!"
The price is NZ$129
includes taxes & fees
20 May - 21 May
Motel 6 Tigard, OR - Portland South - Lake Oswego
Lobby
The Paramount Hotel
3.5 star property
9.2 out of 10, Wonderful, (1860)
"Love this place"
The price is NZ$220
includes taxes & fees
20 May - 21 May
The Paramount Hotel
Lobby
Red Lion Hotel Portland Airport
3.0 star property
7.2 out of 10, Good, (2025)
"Convenient for the Airport ... comparatively decent price ... staff knowledgeable & helpful."
The price is NZ$162
includes taxes & fees
24 May - 25 May
Red Lion Hotel Portland Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lake Oswego holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lake Oswego. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Lake Oswego. Seeing all the best attractions is bound to make you fall in love with Lake Oswego. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Lake Oswego short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Lake Oswego?

Yes, there are holiday rentals in Lake Oswego close to Bike Gallery, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic lakeside in Lake Oswego. While you're here, grab a bite or have a drink at the top-notch restaurants.

What are some of the best holiday rentals that Lake Oswego has to offer?

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row: This holiday home rental outside of Lake Oswego is located on a river, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Lake Oswego?

Choose from 35 Expedia holiday rentals in Lake Oswego for a memorable holiday.

What can I see and do in Lake Oswego?

Cultural attractions include Arts Council of Lake Oswego and Lakewood Center for the Arts, whereas Willamette River and Millenium Plaza City Park are a couple of picturesque spots to enjoy the outdoors. Lake Oswego Farmers' Market and Portland Temple Visitors' Center are other places to visit while you're in town.

What are holiday rentals like in Lake Oswego?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lake Oswego. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.

Recent reviews of Lake Oswego properties
Expedia verified reviews

Heathman Lodge

Heathman Lodge

5/5 Excellent
"Great staff nice place"
A verified traveller stayed at Heathman Lodge
Posted 5 hours ago
Heathman Lodge