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

Milwaukie 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 Milwaukie holiday rentals

1. Inn at Northrup Station

Inn at Northrup Station
3.0 star property
Northwest Portland
9.4 out of 10, Exceptional, (2,262 reviews)
"Cute decor, thoughtful details, great location. Quiet location and parking is easy."
United States
Shannon
The price is NZ$311
includes taxes & fees
26 Oct - 27 Oct
Inn at Northrup Station

2. 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$460
includes taxes & fees
12 Oct - 13 Oct
Oregon Jade Lodging- Spacious 2 Bedrooms, Ev Charger, Quite By Stream

3. Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2,279 reviews)
"Good stay, decent price for what we got. Definitely recommend."
United States
Eric
The price is NZ$175
includes taxes & fees
13 Oct - 14 Oct
Larkspur Landing Extended Stay Suites Hillsboro

4. Pomeroy

Pomeroy
2.0 star property
Northwest Portland
10.0 out of 10, Exceptional, (1 review)
"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$457
includes taxes & fees
30 Sept - 1 Oct
Pomeroy

5. Walk to Park & Creekside Trails! Modern Sandy Home

Walk to Park & Creekside Trails! Modern Sandy Home
3.0 star property
Sandy
Walk to Park & Creekside Trails! Modern Sandy Home
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 Milwaukie Hotel Reviews

Find out more about Milwaukie

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 Milwaukie 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 Milwaukie. 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 Milwaukie. Seeing all the best attractions is bound to make you fall in love with Milwaukie. 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 Milwaukie short-term rentals, that won’t be hard to do.

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.