A forest stream with moss-covered trees and dense undergrowth.

Lake Oswego Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Lake Oswego holiday rentals

1. #StayInMyDistrict Lake Oswego Honey Bee Cottage

#StayInMyDistrict Lake Oswego Honey Bee Cottage
First Addition
9.2 out of 10, Wonderful, (47 reviews)
"Very nice stay. I would just recommend a making the address numbers more visible."
United States
Marlene P.
The price is NZ$488
includes taxes & fees
15 Nov - 16 Nov
#StayInMyDistrict Lake Oswego Honey Bee Cottage

2. Stylish Lake Oswego Retreat - All new high end furnishings and amazing patio

Stylish Lake Oswego Retreat - All new high end furnishings and amazing patio
McVey-South Shore
10.0 out of 10, Exceptional, (49 reviews)
"Once again a great stay here. Wonderful home in a great location "
United States
Greg D.
The price is NZ$1,999
includes taxes & fees
27 Nov - 28 Nov
Stylish Lake Oswego Retreat - All new high end furnishings and amazing patio

3. Delightful 2BR Lakefront - Patio

Delightful 2BR Lakefront - Patio
Blue Heron
The price is NZ$1,550
includes taxes & fees
11 Nov - 12 Nov
Delightful 2BR Lakefront - Patio

4. Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park

Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park
Mount Park
9.8 out of 10, Exceptional, (18 reviews)
"Great location. "
United States
Carrie S.
The price is NZ$353
includes taxes & fees
5 Dec - 6 Dec
Charming 1-Bedroom Entire Condo Loft in Scenic Mountain Park

5. The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors

The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors
Lake Oswego
9.8 out of 10, Exceptional, (27 reviews)
"We really enjoyed our stay. So fun for the kids!"
United States
Stephanie W.
The price is NZ$457
includes taxes & fees
11 Nov - 12 Nov
The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors

6. Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.

Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.
Oak Grove
9.0 out of 10, Wonderful, (20 reviews)
"This was a very comfortable stay, Some quirky features, which give it character. Nice neighbors and neighborhood. We enjoyed our stay very much! Nothing over extravagant, just basic furniture."
United States
Vivian K.
The price is NZ$498
includes taxes & fees
11 Nov - 12 Nov
Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.

7. Inn at Northrup Station

Inn at Northrup Station
3.0 star property
Northwest Portland
9.4 out of 10, Exceptional, (2,286 reviews)
"Really enjoyed our stay. The ambiance is very Portland! The staff was so helpful too."
United States
Celia
The price is NZ$265
includes taxes & fees
16 Nov - 17 Nov
Inn at Northrup Station

8. Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream
2.0 star property
Rosemont Summit
10.0 out of 10, Exceptional, (1 review)
The price is NZ$470
includes taxes & fees
22 Nov - 23 Nov
Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

9. Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2,326 reviews)
"Nice comfortable stay"
United States
Dennis
The price is NZ$172
includes taxes & fees
15 Nov - 16 Nov
Larkspur Landing Extended Stay Suites Hillsboro

10. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Great location near Sellwood shops & tea, bakery & restaurants."
United States
dan v.
The price is NZ$387
includes taxes & fees
11 Nov - 12 Nov
#StayinMyDistrict Sellwood Coco Rose Retreat

11. Walkable Sellwood 2BR Apartment

Walkable Sellwood 2BR Apartment
Southeast Portland
10.0 out of 10, Exceptional, (111 reviews)
"This VRBO apartment is so comfortable and well designed that we hope to stay again on our next visit. It is wonderfully located and charming."
United States
Jane F.
Walkable Sellwood 2BR Apartment

12. Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views
Southwest Portland
10.0 out of 10, Exceptional, (136 reviews)
"The place was very comfortable. Highly recommended."
United States
Raymond C.
The price is NZ$632
includes taxes & fees
11 Nov - 12 Nov
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

13. Beautiful Art Filled Home 15 minutes to Downtown

Beautiful Art Filled Home 15 minutes to Downtown
Ardenwald
10.0 out of 10, Exceptional, (85 reviews)
"Close to shops and restaurants."
United States
Greenie D.
The price is NZ$538
includes taxes & fees
29 Nov - 30 Nov
Beautiful Art Filled Home 15 minutes to Downtown

14. Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland

Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland
Bolton
10.0 out of 10, Exceptional, (26 reviews)
"Just loved the music vibe. Well appointed it’s all those little things I always seem to forget. Loved watching the eagles too"
United States
Robert
The price is NZ$343
includes taxes & fees
15 Nov - 16 Nov
Riverfront Cottage on the Willamette · Blue Heron Sanctuary near Portland

15. Exquisite Forested Retreat, Pet Friendly, Huge Patio w/ Fire-Table and TV, Steps From Dockside

Exquisite Forested Retreat, Pet Friendly, Huge Patio w/ Fire-Table and TV, Steps From Dockside
West Linn
10.0 out of 10, Exceptional, (36 reviews)
"Pretty area"
United States
Jennifer
The price is NZ$713
includes taxes & fees
11 Nov - 12 Nov
Exquisite Forested Retreat, Pet Friendly, Huge Patio w/ Fire-Table and TV, Steps From Dockside

16. Granny Flat in leafy SW Portland

Granny Flat in leafy SW Portland
Southwest Portland
9.6 out of 10, Exceptional, (31 reviews)
"The flat was clean and well-appointed. We stayed multiple nights as we were in Portland to see multiple groups of friends. Great location and close to I5. Bed was very comfy and checkin was a breeze. Communication with the host was seamless. The view from the balcony was serene and the kitchen was well-stocked. Great tasting coffee, too! We've found our go-to for our next trip to town. Thank you!"
United States
Lucy B.
The price is NZ$336
includes taxes & fees
7 Dec - 8 Dec
Granny Flat in leafy SW Portland

17. Pomeroy

Pomeroy
2.0 star property
Northwest Portland
10.0 out of 10, Exceptional, (2 reviews)
"The location of this VRBO was wonderful. Lots of great food options and shopping within easy, safe walking distance. There’s a grocery store 2 blocks away. For those who want to use public transport, the #15 stops at the corner."
United States
Richard
The price is NZ$318
includes taxes & fees
16 Nov - 17 Nov
Pomeroy

18. Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Milwaukie
9.4 out of 10, Exceptional, (130 reviews)
"Great location quiet neighborhood clean home with a nice yard and surroundings. Note that is it a shared property with main home but in separate quarters which was no issue to us as it was a very enjoyable stay."
United States
Karin S.
The price is NZ$555
includes taxes & fees
29 Nov - 30 Nov
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

19. #StayInMyDistrict Multnomah Village Modern Retreat

#StayInMyDistrict Multnomah Village Modern Retreat
Southwest Portland
9.2 out of 10, Wonderful, (29 reviews)
"Clean and spacious"
United States
Ruth A.
The price is NZ$483
includes taxes & fees
11 Nov - 12 Nov
#StayInMyDistrict Multnomah Village Modern Retreat

20. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Portland OR
9.8 out of 10, Exceptional, (60 reviews)
"Great value for what we paid! Spacious room with all we needed for a quick stay, including nice amenities like free toiletries."
United States
Anonymous traveller
The price is NZ$167
includes taxes & fees
12 Nov - 13 Nov
2 Queen Beds Non-Smoking
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$172 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Lake Oswego?

Yes, there are holiday rentals in Lake Oswego close to Arts Council of Lake Oswego, 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?

The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors: This highly rated holiday home rental in Lake Oswego is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave. Other favourite homes for rent in Lake Oswego are Stylish Family Retreat w/ Patio, & Game Console in Heart of Lake Oswego’s Westlake Neighborhood and Palais de Leon - Ultra-Luxury Riverfront Estate, Pool, Spa, Theater, Dock, Hot Tubs, Gym on 3 Acres.

How many holiday rentals are there in Lake Oswego?

Choose from 28 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 Oswego Lake 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.