Milwaukie Holiday Rentals

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Our top choices for Milwaukie holiday rentals

Beautiful Art Filled Home 15 minutes to Downtown

Beautiful Art Filled Home 15 minutes to Downtown
Ardenwald
10.0 out of 10, Exceptional, (73)
"Cute clean house. Very much enjoyed the stay."
United States
John C.
The price is NZ$459
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Art Filled Home 15 minutes to Downtown

Cozy apartment in a lovely and quiet neighborhood

Cozy apartment in a lovely and quiet neighborhood
Milwaukie
9.6 out of 10, Exceptional, (102)
"Great place to stay for a trip. Private and has everything you need. "
United States
Eli S.
The price is NZ$276
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy apartment in a lovely and quiet neighborhood

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Milwaukie
9.6 out of 10, Exceptional, (103)
"The property was lovely. Kitchen is fabulous. Had a lovely stay. Would highly recommend. The host was easy to communicate with and very accommodating. "
United States
Sally
The price is NZ$596
includes taxes & fees
11 Jan - 12 Jan 2026
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Margaux the Vintage Airstream - Portland's Glamping Garden Oasis
2.0 star property
Southeast Portland
9.6 out of 10, Exceptional, (7)
"Amazing host with great communication, a gorgeous and perfectly placed spot, and a fun, cozy place that had everything I needed. The commissary was incredible, and the whole experience was perfect!"
United States
Kierra P.
The price is NZ$259
includes taxes & fees
4 Jan - 5 Jan 2026
Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2037)
" Excellent for our weekend stay."
United States
MEREDITH
The price is NZ$154
includes taxes & fees
5 Jan - 6 Jan 2026
Larkspur Landing Extended Stay Suites Hillsboro

#StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
2.0 star property
Southeast Portland
10.0 out of 10, Exceptional, (33)
"Beautiful little space, steps away from great food and coffee."
United States
Christine M.
The price is NZ$352
includes taxes & fees
6 Jan - 7 Jan 2026
#StayinMyDistrict Sellwood Coco Rose Retreat

Cozy Wine Country Suite

Cozy Wine Country Suite
Sherwood - Tualatin South
9.4 out of 10, Exceptional, (16)
"The room was clean, well appointed,ina great location, and we enjoyed our short stay. Would definitely stay here again when in the area. "
United States
Brayden C.
The price is NZ$203
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Wine Country Suite

#StayInMyDistrict St. Johns Bungalow

#StayInMyDistrict St. Johns Bungalow
2.0 star property
North Portland
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 NZ$520
includes taxes & fees
4 Jan - 5 Jan 2026
#StayInMyDistrict St. Johns Bungalow

#StayinMyDistrict Alberta Arts Daylight Studio

#StayinMyDistrict Alberta Arts Daylight Studio
2.0 star property
Northeast Portland
10.0 out of 10, Exceptional, (7)
"I had a wonderful stay "
United States
Sharada B.
The price is NZ$399
includes taxes & fees
29 Jan - 30 Jan 2026
#StayinMyDistrict Alberta Arts Daylight Studio

Downtown Camas Apartment

Downtown Camas Apartment
Camas
10.0 out of 10, Exceptional, (8)
"We had a great visit in Camas. Easy access to freeway and still very quiet."
United States
James F.
The price is NZ$319
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Camas Apartment

Private, cozy, airy garden studio suite, for 1 or 2 guests

Private, cozy, airy garden studio suite, for 1 or 2 guests
Northeast Portland
9.8 out of 10, Exceptional, (20)
"Beautiful location, not far from dowtown portland, and was a very relaxing stay."
United States
Kelsey L.
The price is NZ$261
includes taxes & fees
5 Jan - 6 Jan 2026
Private, cozy, airy garden studio suite, for 1 or 2 guests

❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE

❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE
Northeast Portland
9.8 out of 10, Exceptional, (152)
"Great location, comfortable and well stocked!"
United States
Edla P.
The price is NZ$432
includes taxes & fees
2 Jan - 3 Jan 2026
❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE

BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT

BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
Northeast Portland
9.6 out of 10, Exceptional, (19)
"Lovely space. Easy to find. Very accessible. Host is an excellent communicator. We loved staying below a home filled with children and loving energy. We especially loved hearing the patter of little feet :-) "
United States
Anne deLain W C.
The price is NZ$537
includes taxes & fees
31 Dec - 1 Jan 2026
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT

Private Basement Guest Suite w/Hot Tub

Private Basement Guest Suite w/Hot Tub
2.0 star property
Camas
9.2 out of 10, Wonderful, (9)
"We enjoyed our stay. The location is great, the decor is attractive and the setting is comfortable. "
United States
Sheila O.
Private Basement Guest Suite w/Hot Tub

Vibrant Portland Getaway - Chic Flat

Vibrant Portland Getaway - Chic Flat
2.0 star property
Southeast Portland
10.0 out of 10, Exceptional, (4)
"Great spot right in the heart of SE Portland!"
United States
Scotty S.
The price is NZ$435
includes taxes & fees
26 Jan - 27 Jan 2026
Vibrant Portland Getaway - Chic Flat

#StayInMyDistrict Downtown Loft

#StayInMyDistrict Downtown Loft
Downtown Vancouver
9.6 out of 10, Exceptional, (7)
"Great location highly recommended"
United States
John B.
The price is NZ$330
includes taxes & fees
4 Jan - 5 Jan 2026
#StayInMyDistrict Downtown Loft

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, (120)
"Check in was easy - and kitchen had everything necessary to make our stay enjoyable. We especially appreciated the electric kettle!"
United States
Lynne R.
The price is NZ$641
includes taxes & fees
3 Jan - 4 Jan 2026
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

Private Greenhouse Suite for 1 or 2 Guests

Private Greenhouse Suite for 1 or 2 Guests
Northeast Portland
10.0 out of 10, Exceptional, (17)
"Nice neighborhood, very convenient for us"
United States
Ted B.
The price is NZ$328
includes taxes & fees
7 Jan - 8 Jan 2026
Private Greenhouse Suite for 1 or 2 Guests

Retro Hideaway - Trendy Location - 2BR - Sleeps 4

Retro Hideaway - Trendy Location - 2BR - Sleeps 4
2.0 star property
Northeast Portland
10.0 out of 10, Exceptional, (4)
"Great spot, either walking distance or many great restaurants or just a short drive away. "
United States
Bryan R.
The price is NZ$552
includes taxes & fees
5 Jan - 6 Jan 2026
Retro Hideaway - Trendy Location - 2BR - Sleeps 4

#StayinMyDistrict Sellwood Private Garden Casita

#StayinMyDistrict Sellwood Private Garden Casita
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 NZ$349
includes taxes & fees
4 Jan - 5 Jan 2026
#StayinMyDistrict Sellwood Private Garden Casita
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$154 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. 

Frequently asked questions

Can I find holiday rentals in Milwaukie?

Yes, there are holiday rentals in Milwaukie close to Bike N Hike, 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?

Live the Dream on the Beautiful Willamette River: This highly rated holiday home rental in Milwaukie is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Milwaukie?

Choose from 41 Expedia holiday rentals in Milwaukie for a memorable holiday.

What can I see and do in Milwaukie?

Family-friendly attractions include Bike N Hike and North Clackamas Aquatic Park, whereas Willamette River and Elk Rock Island are a couple of great spots to enjoy the outdoors. Milwaukie Farmers Market and Milwaukie Museum 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.