Lake Oswego Holiday Rentals

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Our top choices for Lake Oswego holiday rentals

Holiday Home in First Addition

9.6 out of 10, Exceptional, (33)
"Wonderful walking neighborhood, close to all that Lake Oswego has to offer!"
United States
john w.
The price is AU$404
includes taxes & fees
14 Dec - 15 Dec
#StayInMyDistrict Lake Oswego Honey Bee Cottage

Condo in Mount Park

9.8 out of 10, Exceptional, (14)
"We stayed for two nights; the location was great, quiet, easy access to everything we needed. "
United States
Deborah B.
The price is AU$270
includes taxes & fees
15 Dec - 16 Dec
Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park

Holiday Home in Oak Creek

9.8 out of 10, Exceptional, (114)
"Very accommodating, especially for our annual guys trip, where 5 men appreciate having their own space, but also like have place to get together for happy hour. Beds comfortable, communication was instantaneous, and everything was provided as marketed.Very nice property in safe area."
United States
K L.
The price is AU$519
includes taxes & fees
11 Dec - 12 Dec
La Casa with Luxury Amenities -hot tub and massage chair

Holiday Home in Lake Oswego

9.2 out of 10, Wonderful, (5)
"Good location, quite neighborhood, the house is clean and nice backyard patio to enjoy & relax"
United States
Khanhh L.
The price is AU$506
includes taxes & fees
14 Dec - 15 Dec
The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors

Holiday Home in Lake Oswego

The price is AU$548
includes taxes & fees
9 Jan - 10 Jan 2026
Cottage next to historical home in Lake Oswego

Mobile Home in Southeast Portland

2.0 star property
9.4 out of 10, Exceptional, (6)
"Everything that we needed for a quiet night away from a busy life. Thank you!! We will definitely come back. "
United States
Dana S.
The price is AU$231
includes taxes & fees
10 Dec - 11 Dec
Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Aparthotel in Hillsboro

3.0 star property
8.2 out of 10, Very good, (2017)
"Very clean room, breakfast was very good"
United States
Brett
The price is AU$166
includes taxes & fees
12 Dec - 13 Dec
Larkspur Landing Extended Stay Suites Hillsboro

Aparthotel in Northwest Portland

3.0 star property
9.4 out of 10, Exceptional, (2131)
"Nice hotel"
United States
Nancy
The price is AU$260
includes taxes & fees
28 Dec - 29 Dec
Inn at Northrup Station

Holiday Home in Southeast Portland

2.0 star property
10.0 out of 10, Exceptional, (33)
"Lovely gardens patio great bed small but comfy"
United States
Jeff M.
The price is AU$321
includes taxes & fees
10 Dec - 11 Dec
#StayinMyDistrict Sellwood Coco Rose Retreat

Apartment in Southeast Portland

9.2 out of 10, Wonderful, (15)
"What a little slice of heaven! Perfect location and comfortable. I’ll be back:)"
United States
Amy C.
The price is AU$300
includes taxes & fees
10 Dec - 11 Dec
#StayinMyDistrict Sellwood Private Garden Casita

Apartment in Northeast Portland

9.8 out of 10, Exceptional, (18)
"Beautiful location, not far from dowtown portland, and was a very relaxing stay."
United States
Kelsey L.
The price is AU$232
includes taxes & fees
16 Dec - 17 Dec
Private, cozy, airy garden studio suite, for 1 or 2 guests

Holiday Home in Gresham

9.6 out of 10, Exceptional, (21)
"The location is great. Very clean and quiet right on the beautiful beach. rooms are on the small side but comfortable. Would definitely recommend. "
United States
Shawn P.
The price is AU$453
includes taxes & fees
10 Dec - 11 Dec
#StayinMyDistrict Gorge-Mt Hood

Holiday Home in Northeast Portland

9.6 out of 10, Exceptional, (19)
"There's a narrow stairway down but it opens up into a big unit with some great beds for the kids. Huge TV, nice kitchen. Would stay here again when visiting the East side of Portland."
United States
Ariel S.
The price is AU$480
includes taxes & fees
10 Dec - 11 Dec
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT

Apartment in Northeast Portland

2.0 star property
10.0 out of 10, Exceptional, (6)
"I had a wonderful stay "
United States
Sharada B.
The price is AU$358
includes taxes & fees
14 Dec - 15 Dec
#StayinMyDistrict Alberta Arts Daylight Studio

Apartment in Northeast Portland

9.8 out of 10, Exceptional, (150)
"Fantastic property and great hosts. Very well appointed property and great location. "
United States
Shelli L.
The price is AU$383
includes taxes & fees
15 Dec - 16 Dec
❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE

Apartment in Northeast Portland

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great property in a fantastic location in North Portland!"
United States
Anish D.
The price is AU$314
includes taxes & fees
10 Dec - 11 Dec
Modern & Bright Walkable Alberta Condo, Fast WiFi

Condo in Northwest Portland

9.0 out of 10, Wonderful, (89)
"Great location, good space in a building with good amenities."
United States
Gretchen W.
The price is AU$520
includes taxes & fees
10 Dec - 11 Dec
Newly Finished Nob Hill Condo w/ Great Walkability and Central Location

Holiday Home in North Portland

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great property. Comfortable, clean, and easy communication with the host. I am looking forward to staying here again in the future."
United States
Sarah J.
The price is AU$462
includes taxes & fees
10 Dec - 11 Dec
#StayInMyDistrict St. Johns Bungalow

Apartment in Sherwood - Tualatin South

9.4 out of 10, Exceptional, (16)
"Check in was easy and convenient. The mattress was new and very comfortable! Towels were a little mildewy, but overall, a good stay. "
United States
Gina C.
The price is AU$197
includes taxes & fees
15 Dec - 16 Dec
Cozy Wine Country Suite

Apartment in Northeast Portland

10.0 out of 10, Exceptional, (16)
"Nice neighborhood, very convenient for us"
United States
Ted B.
The price is AU$291
includes taxes & fees
16 Dec - 17 Dec
Private Greenhouse Suite for 1 or 2 Guests
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.
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Top Lake Oswego Hotel Reviews

Find out more about Lake Oswego

Everything you need to know about Lake Oswego holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lake Oswego holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lake Oswego holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Lake Oswego holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lake Oswego. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lake Oswego holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lake Oswego holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Lake Oswego rentals

At Expedia, we put the best Lake Oswego holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lake Oswego rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lake Oswego holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lake Oswego. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Lake Oswego?

Yes, there are holiday rentals in Lake Oswego close to Willamette Shore Trolley, 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?

World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland: This holiday home rental outside of Lake Oswego offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Lake Oswego?

Choose from 33 Expedia holiday rentals in Lake Oswego for a memorable holiday.

What can I see and do in Lake Oswego?

Cultural attractions include Lakewood Center for the Arts and Arts Council of Lake Oswego, whereas Willamette River and Millenium Plaza City Park are a couple of picturesque spots to enjoy the outdoors. Lake Oswego Farmers' Market and Willamette Shore Trolley 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.