Milwaukie Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Milwaukie holiday rentals

Outdoor dining
Beautiful Art Filled Home 15 minutes to Downtown

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 HK$1,248
HK$2,151 total
includes taxes & fees
29 Dec - 30 Dec
Beautiful Art Filled Home 15 minutes to Downtown
Property grounds
Cozy apartment in a lovely and quiet neighborhood

Cozy apartment in a lovely and quiet neighborhood

Cozy apartment in a lovely and quiet neighborhood
Milwaukie
9.6 out of 10, Exceptional, (101)
"Great place to stay for a trip. Private and has everything you need. "
United States
Eli S.
The price is HK$574
HK$1,253 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy apartment in a lovely and quiet neighborhood
Property grounds
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

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 HK$1,104
HK$2,816 total
includes taxes & fees
11 Jan - 12 Jan 2026
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Terrace/patio
Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Margaux the Vintage Airstream - Portland's Glamping Garden Oasis
2.0 star property
Southeast Portland
9.4 out of 10, Exceptional, (6)
"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 HK$560
HK$1,176 total
includes taxes & fees
29 Dec - 30 Dec
Margaux the Vintage Airstream - Portland's Glamping Garden Oasis
Exterior
Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro

Larkspur Landing Extended Stay Suites Hillsboro
3.0 star property
Hillsboro
8.2 out of 10, Very good, (2033)
" Excellent for our weekend stay."
United States
MEREDITH
The price is HK$621
HK$705 total
includes taxes & fees
1 Jan - 2 Jan 2026
Larkspur Landing Extended Stay Suites Hillsboro
Terrace/patio
#StayinMyDistrict Sellwood Coco Rose Retreat

#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 HK$420
HK$1,559 total
includes taxes & fees
30 Dec - 31 Dec
#StayinMyDistrict Sellwood Coco Rose Retreat
Property grounds
Cozy Wine Country Suite

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 HK$385
HK$922 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Wine Country Suite
Fridge, microwave, oven, stovetop
#StayInMyDistrict St. Johns Bungalow

#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 HK$672
HK$2,287 total
includes taxes & fees
29 Dec - 30 Dec
#StayInMyDistrict St. Johns Bungalow
Fridge, microwave, oven, stovetop
#StayinMyDistrict Alberta Arts Daylight Studio

#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 HK$405
HK$1,496 total
includes taxes & fees
29 Dec - 30 Dec
#StayinMyDistrict Alberta Arts Daylight Studio
Fridge, microwave, oven, stovetop
Downtown Camas Apartment

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 HK$855
HK$1,445 total
includes taxes & fees
3 Jan - 4 Jan 2026
Downtown Camas Apartment
Exterior detail
Private, cozy, airy garden studio suite, for 1 or 2 guests

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 HK$363
HK$1,183 total
includes taxes & fees
5 Jan - 6 Jan 2026
Private, cozy, airy garden studio suite, for 1 or 2 guests
Smart TV, books, music library, video library
❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE

❤️ 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 HK$539
HK$1,918 total
includes taxes & fees
29 Dec - 30 Dec
❤️ CLEAN ★ NEAR DOWNTOWN | PRIVATE PATIO ★ WALKABLE
Fridge, microwave, oven, stovetop
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT

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 HK$676
HK$2,437 total
includes taxes & fees
30 Dec - 31 Dec
BOOK 7 NITES AND GET A DISCOUNT 2 BEDROOM PRIVATE UNIT
TV
Private Basement Guest Suite w/Hot Tub

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
Interior
Vibrant Portland Getaway - Chic Flat

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 HK$865
HK$1,971 total
includes taxes & fees
26 Jan - 27 Jan 2026
Vibrant Portland Getaway - Chic Flat
Outdoor dining
#StayInMyDistrict Downtown Loft

#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 HK$448
HK$1,490 total
includes taxes & fees
30 Dec - 31 Dec
#StayInMyDistrict Downtown Loft
Fridge, microwave, oven, stovetop
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views

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 HK$1,017
HK$2,909 total
includes taxes & fees
3 Jan - 4 Jan 2026
Modern Portland Condo, Near Zupan’s, OHSU, River Trails, Dining & Skyline Views
Interior
Private Greenhouse Suite for 1 or 2 Guests

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 HK$588
HK$1,488 total
includes taxes & fees
7 Jan - 8 Jan 2026
Private Greenhouse Suite for 1 or 2 Guests
Outdoor dining
Retro Hideaway - Trendy Location - 2BR - Sleeps 4

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 HK$841
HK$2,488 total
includes taxes & fees
5 Jan - 6 Jan 2026
Retro Hideaway - Trendy Location - 2BR - Sleeps 4
Exterior detail
#StayinMyDistrict Sellwood Private Garden Casita

#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 HK$385
HK$1,515 total
includes taxes & fees
29 Dec - 30 Dec
#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

AC Hotel by Marriott Portland Downtown, OR

AC Hotel by Marriott Portland Downtown, OR

10/10 Excellent
" Nice spot. Super convenient for in/out around town. Room was slick. I would be stoked to stay again. "
Joel 1-night trip
Posted 1 day ago
AC Hotel by Marriott Portland Downtown, OR

Find out more about Milwaukie

Search for holiday rentals in Milwaukie on Expedia! You can easily find your home rentals, villas, holiday apartments in Milwaukie using one of the methods below:

  • View our selection of featured holiday rentals in Milwaukie
  • Use the map to find apartments and other holiday homes in the Milwaukie neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Milwaukie while they last

Look no further and take a look at our great range of rental properties in Milwaukie!

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 Lovely 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.