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Portland, Oregon, is one of my favorite cities in the U.S. It has incredible restaurants, stunning parks, a great art scene, and many outdoor activities, especially near Mt. Hood and the Columbia River Gorge. So I’ve rounded up the best vacation home rentals in Portland, Oregon.
Plan The Perfect Trip To Portland, Oregon
Whether you’re on a road trip around the Pacific Northwest or you’re looking for a weekend getaway, you’ll fall in love with these unique, inviting, and cozy homes.
Here are the coolest vacation home rentals in Portland, Oregon!
Sun-Filled Home
5 guests bedrooms beds1 bath
Built in 1911, this craftsman-style home is the perfect mix of modern amenities and vintage charm. The home is in a historic neighborhood close to downtown, parks, the Alberta Arts District, and restaurants. You’ll love the high ceilings, large original windows, original vintage fixtures, and the rough-hewn stone fireplace
Modern Skyhouse
8 guests bedrooms beds baths
This home’s cutting-edge architecture and design make it one of the most unique houses in the city. You’ll feel like you’re floating above Forest Park with incredible views of the Willamette Valley and the Oregon Coast Range.
Urban Oasis
8 guests beds bathrooms
You’ll love this home’s iconic pacific northwest architecture. The house is close to downtown, parks, and trails. This home also has an open floor plan, large windows, spacious living and dining areas, and a large fenced-in backyard with a BBQ.
Mid-Century Modern
6 guests beds baths
This newly renovated home has some of the best views in the city. You’ll love the open living and dining rooms, spa-like bathrooms, mid-century furniture and decor, and the wrap-around deck with a BBQ and al fresco dining.
Chic Apartment
2 guests1 bedroom1 bed1 bath
This newly built condo unit is light, bright, airy, and minimalist, making it a tranquil city getaway. This is a budget-friendly accommodation in Portland, and you’ll love the city views.
Forest Retreat
4 guests bedrooms beds1 bath
Get ready to fall in love with this secluded and wooded retreat just minutes from downtown. This colorful, cozy house is located on the edge of the Wildwood Trail that connects Washington Park and Forest Park. So this is the perfect home for outdoor lovers.
Castle Estate
16 guests bedrooms beds3 baths
Have you ever wanted to stay in a castle? Then this elaborate home is for you! You’ll fall in love with the house’s architecture and views. There are vaulted ceilings, curved rooms, two fireplaces, beautiful tile work, hardwood floors, two jacuzzis, and a hot tub.
Million-Dollar Views
3 guests1 bedroom2 beds1 bath
If you want a property that makes you feel like you’re in a high-end hotel, then this highrise apartment is for you. This home is in the heart of the city, just two blocks from Pioneer Courthouse Square and five blocks from the Pearl District. You’ll have incredible views of the city, and you can bring your furry friends with you.
Recommended Tours in Portland
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What are your favorite vacation home rentals in Portland, Oregon? Share with us in the comments!
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Vacation Home Rentals in Portland, Oregon
Frequently Asked Questions
How much does it cost to rent a vacation home in Portland, Oregon?
The average nightly rate of a vacation home in Portland, Oregon, is around $150 per night. Vacation home prices are highest during the summer, and the lowest vacation home prices are in the winter.
What is the best time of year to go to Portland, Oregon?
Portland is a year-round destination. But depending on what you want to do, some seasons will be better than others for you to visit. June – August has the warmest, sunniest weather. The city’s roses are in full bloom, and the summer is when the city’s outdoorsy culture thrives. But these months are also the most crowded and expensive, so budget accordingly and book ahead of time.
From March – May, you can experience the city’s Spring beauty while beating the summer crowds and prices. Temperatures will be in the mid-40s to upper 60s (7 – 20ºC), so bring layers, and be prepared for rain.
In September – November, the city’s deciduous trees turn beautiful colors, Mt. Hood and the Columbia River Gorge are still fully open and accessible, and the summer crowds and prices will taper off. Temperatures will drop from the mid-70s to low 50s (24 – 11ºC) as Fall progresses, so pack accordingly. There’s less chance of rain in Autumn than Spring, but make sure you still have rain gear.
If you’re here from December – February, be prepared for rain every day. Museums will be open, but the parks and gardens have reduced hours, so always confirm opening and closing times beforehand. While the city usually doesn’t get cold enough for snow, Mt. Hood has plenty of snow this time of year, so you can take day trips to its slopes.
Is Portland, Oregon a walkable city?
Portland is a very walkable city. Portland also has good public transportation and is very bikeable.
Is Portland or Seattle better to visit?
Portland and Seattle are both incredible destinations, and they will each give you very different experiences.
Seattle is usually more popular, expensive, and crowded than Portland, and Seattle has a bigger city “vibe.”
Portland is traditionally less-visited with a “chiller” vibe than Seattle. Both cities have fantastic foodie scenes, great outdoor activities, and beautiful architecture, so I highly recommend visiting both of these cities!
What is there to do in Portland, Oregon?
Top things to do in Portland, Oregon:
1. Explore Pittock Mansion
2. Visit Pioneer Courthouse Square, aka “Portland’s Living Room”
3. Hike in Forest Park – an urban forest reserve
4. Relax at the Japanese Garden
5. See The Grotto
6. Do a Pub Crawl
7. Ride the Arial Tram
8. Take a photo in front of the White Stag Sign
9. Visit Cathedral Park
10. Visit the Columbia River Gorge
What are the best viewpoints in Portland, Oregon?
Where to go for the best views of Portland and Mount Hood:
1. Upper OHSU Tram Station
2. Eastbank Esplanade
3. Rocky Butte
4. Pittock Mansion (pictured above)
5. Japanese Garden
6. Mount Tabor Park
7. Willamette Falls Viewpoint
8. Sunrise Point
How many days do you need to visit Portland, Oregon?
Give yourself at least 3-4 days to explore Portland. This will give you plenty of time to see the sites, enjoy the food scene, and take a day trip.
What should I not miss in Portland, Oregon?
Top things to do in Portland, Oregon:
1. Explore Pittock Mansion
2. Visit Pioneer Courthouse Square, aka “Portland’s Living Room”
3. Hike in Forest Park – an urban forest reserve
4. Relax at the Japanese Garden
5. See The Grotto
6. Do a Pub Crawl
7. Ride the Arial Tram
8. Take a photo in front of the White Stag Sign
9. Visit Cathedral Park
10. Visit the Columbia River Gorge
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This article about the best Vacation Home Rentals in Portland, Oregon, is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the best Vacation Home Rentals in Portland, Oregon are affiliate links, and, at no cost to you, I may earn a small commission.
