A calm lake with reflections of houses and trees, surrounded by a forested area and a cloudy sky.

Milwaukie Holiday Rentals

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Our top choices for Milwaukie holiday rentals

1. 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$537
includes taxes & fees
29 Nov - 30 Nov
Beautiful Art Filled Home 15 minutes to Downtown

2. 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$569
includes taxes & fees
10 Dec - 11 Dec
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

3. Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland

Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland
Oak Grove
9.6 out of 10, Exceptional, (7 reviews)
"My husband and I really enjoyed our stay here. It was very cute and clean. The VRBO building is very close to the main house on the property, but we had no issues with that."
United States
Brittany P.
The price is NZ$529
includes taxes & fees
14 Nov - 15 Nov
Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland

4. Peaceful 2-bedroom Duplex in charming Milwaukie awaits you

Peaceful 2-bedroom Duplex in charming Milwaukie awaits you
Ardenwald
The price is NZ$562
includes taxes & fees
17 Nov - 18 Nov
Peaceful 2-bedroom Duplex in charming Milwaukie awaits you

5. 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$477
includes taxes & fees
16 Nov - 17 Nov
Cowboy Cabana! Hot Tub and Ping Pong! Cozy 3 bedroom home.

6. Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard

Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard
Oatfield
9.8 out of 10, Exceptional, (19 reviews)
"The house was clean and really cute. The set up was great for our stay and host was super helpful. Really enjoyed our stay!"
United States
Dana F.
The price is NZ$467
includes taxes & fees
23 Nov - 24 Nov
Haven Guesthouse in Milwaukie - 2 Bedroom & 2 Bathroom with Fenced Backyard

7. Spacious Home• Gazebo• BBQ• Full Kitchen• 3BR

Spacious Home• Gazebo• BBQ• Full Kitchen• 3BR
Oatfield
9.0 out of 10, Wonderful, (2 reviews)
"Great for myself, partner, kid and grandparents. We had plenty of space to spend time together. Having two full bathrooms was a plus! The backyard is also comfortable and a nice addition."
United States
Trent H.
The price is NZ$964
includes taxes & fees
15 Nov - 16 Nov
Spacious Home• Gazebo• BBQ• Full Kitchen• 3BR

8. Walkable Sellwood 2BR Apartment

Walkable Sellwood 2BR Apartment
Southeast Portland
10.0 out of 10, Exceptional, (111 reviews)
"This VRBO was a very comfortable place to stay in, in a wonderful location. The host was very communicative and we would recommend others to stay there!"
United States
Mary Jo K.
Walkable Sellwood 2BR Apartment

9. #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$402
includes taxes & fees
15 Nov - 16 Nov
#StayinMyDistrict Sellwood Coco Rose Retreat

10. #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$533
includes taxes & fees
7 Dec - 8 Dec
#StayInMyDistrict Lake Oswego Honey Bee Cottage

11. 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$619
includes taxes & fees
30 Nov - 1 Dec
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

12. Inn at Northrup Station

Inn at Northrup Station
3.0 star property
Northwest Portland
9.4 out of 10, Exceptional, (2,287 reviews)
"Really enjoyed our stay. The ambiance is very Portland! The staff was so helpful too."
United States
Celia
The price is NZ$257
includes taxes & fees
30 Nov - 1 Dec
Inn at Northrup Station

13. 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$1,993
includes taxes & fees
27 Nov - 28 Nov
Stylish Lake Oswego Retreat - All new high end furnishings and amazing patio

14. Large Cozy Home

Large Cozy Home
Southgate
9.6 out of 10, Exceptional, (60 reviews)
"Very nice place, comfortable beds, and very clean! We enjoyed our stay very much!"
United States
Breanna D.
The price is NZ$899
includes taxes & fees
15 Nov - 16 Nov
Large Cozy Home

15. Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2,329 reviews)
"excellent place to stay and affordable. second time staying here and would recommend to others."
United States
Sarijah
The price is NZ$170
includes taxes & fees
15 Nov - 16 Nov
Larkspur Landing Extended Stay Suites Hillsboro

16. Margaux · 1967 Airstream · Garden Glamping · PDX

Margaux · 1967 Airstream · Garden Glamping · PDX
Southeast Portland
9.8 out of 10, Exceptional, (21 reviews)
"Great stay at Kayla's Airstream, Margaux. Perfect location and wonderful host. Highly recommend!"
United States
marcus c.
The price is NZ$249
includes taxes & fees
16 Nov - 17 Nov
Margaux · 1967 Airstream · Garden Glamping · PDX

17. #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$488
includes taxes & fees
15 Nov - 16 Nov
#StayInMyDistrict Multnomah Village Modern Retreat

18. 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$317
includes taxes & fees
16 Nov - 17 Nov
Pomeroy

19. 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$469
includes taxes & fees
7 Dec - 8 Dec
Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

20. #StayinMyDistrict Pendelton Place Walk to Mt Tabor

#StayinMyDistrict Pendelton Place Walk to Mt Tabor
Southeast Portland
8.4 out of 10, Very good, (21 reviews)
"Cozy"
United States
Brian K.
The price is NZ$401
includes taxes & fees
17 Nov - 18 Nov
#StayinMyDistrict Pendelton Place Walk to Mt Tabor
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 Milwaukie Hotel Reviews

Find out more about Milwaukie

Everything you need to know about Milwaukie 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 Milwaukie 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 Milwaukie holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Milwaukie holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Milwaukie. 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 Milwaukie 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 Milwaukie holiday rentals we have selected for you start as low as NZ$170 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Milwaukie rentals

At Expedia, we put the best Milwaukie 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 Milwaukie 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 Milwaukie 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 Milwaukie. 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 Milwaukie?

Yes, there are holiday rentals in Milwaukie close to North Clackamas Aquatic Park, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Milwaukie is known for its shops. Make sure you have time to check out the sporting events and lake views during your trip.

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

Magnificent Home on Banks of the Willamette River, Hot Tub, Fire-Pit, Cornhole, 9 Miles to Downtown: This highly rated holiday home rental in Milwaukie is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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 Access to hot tub in this rental home to help you unwind. Some other top choices in Milwaukie are Pacific Northwest Luxury with 270° River Views, Hot Tub, Billiards, Shuffleboard, Karaoke, BBQ and Private Oasis on the Beautiful Willamette River.

How many holiday rentals are there in Milwaukie?

Choose from 47 Expedia holiday rentals in Milwaukie for a memorable holiday.

What can I see and do in Milwaukie?

Family-friendly attractions include North Clackamas Aquatic Park and Bike N Hike, whereas Willamette River and Elk Rock Island are a couple of great spots to enjoy the outdoors. Milwaukie Museum and Milwaukie Farmers Market are other places to visit while you're in town.

What are holiday rentals like in Milwaukie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Milwaukie. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.