Milwaukie Holiday Rentals

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Our top choices for Milwaukie holiday rentals

Holiday Home in Island Station

Live the Dream on the Lovely Willamette River
9.4 out of 10, Exceptional, (205)
"Great host and property"
United States
Jason W.
Live the Dream on the Lovely Willamette River
9.6 out of 10, Exceptional, (100)
"Great place to stay for a trip. Private and has everything you need. "
United States
Eli S.
The price is AU$234
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy apartment in a lovely and quiet neighborhood
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 AU$508
includes taxes & fees
21 Dec - 22 Dec
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
3.0 star property
8.2 out of 10, Very good, (2017)
"Very clean room, breakfast was very good"
United States
Brett
The price is AU$167
includes taxes & fees
31 Dec - 1 Jan 2026
Larkspur Landing Extended Stay Suites Hillsboro

Aparthotel in Northwest Portland

Inn at Northrup Station
3.0 star property
9.4 out of 10, Exceptional, (2132)
"Room was clean, staff was friendly"
United States
Enrique Gonzalez
The price is AU$260
includes taxes & fees
28 Dec - 29 Dec
Inn at Northrup Station
10.0 out of 10, Exceptional, (33)
"This was a fantastic house for our family reunion. It comfortably accomodated our group of 16. The kitchen was well appointed, beds clean and the game room, pool, extensive outdoor space and beautiful surroundings made this a truly memorable stay! The location is very convenient to Portland. Hosts were very responsive. Highly recommend!"
United States
Zainab K.
World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland
10.0 out of 10, Exceptional, (326)
"Great location and easy check in! Property was as described and our family had a great stay."
United States
Deanna & Peter M.
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

Apartment in Walluga

Quarry Commons
3.0 star property
Quarry Commons
10.0 out of 10, Exceptional, (19)
"We had a group of 6 attending the Craft Wine event and it was a great location with a great space! "
United States
Athena B.
The price is AU$660
includes taxes & fees
7 Jan - 8 Jan 2026
2,100 SqFt Contemporary Home W/ Jacuzzi & Fire Pit

Holiday Home in Southeast Portland

Tiny Farmhouse - Walk to Local Shops & Restaurants
10.0 out of 10, Exceptional, (3)
"First (and not last) tiny home stay! Perfectly appointed and comfortable space. Conveniently located with ample street parking. Great experience - would definitely book again."
United States
Darleen S.
The price is AU$280
includes taxes & fees
14 Dec - 15 Dec
Tiny Farmhouse - Walk to Local Shops & Restaurants
9.8 out of 10, Exceptional, (319)
"great get away and location. "
United States
Mark G.
The price is AU$277
includes taxes & fees
14 Dec - 15 Dec
Pet friendly apartment with covered patio and fenced-in yard.

Apartment in Northeast Portland

Portland Sanctuary
9.8 out of 10, Exceptional, (100)
"Great stay, lovely place, excellent communication. "
United States
Jen S.
The price is AU$392
includes taxes & fees
14 Dec - 15 Dec
Portland Sanctuary
9.0 out of 10, Wonderful, (35)
"Place was clean and cozy. Host was very informative for check in process. Views were great to wake up to in the morning and hot tub was a good relaxer after a good day of exploring. Would definitely stay here again."
United States
Evelyn M.
The price is AU$393
includes taxes & fees
17 Dec - 18 Dec
The "Old Barn" in the woods. Peace, Romance, Ahhh
10.0 out of 10, Exceptional, (97)
"Wonderful stay at quaint location"
United States
Yvonne M.
The price is AU$287
includes taxes & fees
12 Dec - 13 Dec
Springdale Farm & Views - the Gorge, Downtown, Mt. Hood

Holiday Home in Harney Heights

A Grand House
9.8 out of 10, Exceptional, (39)
"Lovely little guest house north of Portland. Great parking, comfy beds, and very commincative host."
United States
Mary V.
The price is AU$501
includes taxes & fees
30 Dec - 31 Dec
A Grand House

Apartment in Northeast Portland

Modern Sanctuary in the heart of Concordia
10.0 out of 10, Exceptional, (139)
"We enjoyed our stay! It was very clean and convenient to walking to restaurants in the area."
United States
Karen K.
The price is AU$371
includes taxes & fees
19 Dec - 20 Dec
Modern Sanctuary in the heart of Concordia

Holiday Home in Walnut Grove

Peace House
2.0 star property
6.4 out of 10, (6)
"We enjoyed our stay. The house was lovely and clean. Our host was very easy to get a hold of and our check in was easy. The kitchen had everything we needed for our two day stay We would stay here again. "
United States
Anonymous traveller
The price is AU$655
includes taxes & fees
17 Dec - 18 Dec
Peace House
2.0 star property
9.4 out of 10, Exceptional, (6)
"Everything that we needed for a quiet night away from a busy life. Thank you!! We will definitely come back. "
United States
Dana S.
The price is AU$230
includes taxes & fees
17 Dec - 18 Dec
Margaux the Vintage Airstream - Portland's Glamping Garden Oasis

Holiday Home in Ellsworth

Bungalow Guest House
8.8 out of 10, Excellent, (33)
"Had an amazing stay!"
United States
Gabriel S.
The price is AU$293
includes taxes & fees
21 Dec - 22 Dec
Bungalow Guest House
9.8 out of 10, Exceptional, (20)
"Comfortable and cozy stay near everything we needed. "
United States
Verenice S.
Eco-friendly Tiny Home in Alberta Arts District
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 favourite 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 depend 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 AU$167 per night. Entering your travel dates in the search wizard might find you 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 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 39 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.