Sylvan - Highlands - Southwest Hills Vacations from $223

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Your Sylvan - Highlands - Southwest Hills Vacation

Whether you're into its views or hiking, the neighborhood of Sylvan - Highlands - Southwest Hills has plenty to keep you occupied. Uncover all of this and more with ease by reserving a Sylvan - Highlands - Southwest Hills vacation package. Some popular nearby attractions to see during your trip to Sylvan - Highlands - Southwest Hills include Oregon Zoo, Portland State University and Portland Japanese Garden. Stop dreaming and start doing. When it's time to book your vacation to Sylvan - Highlands - Southwest Hills, Expedia is here to help.

The Latest Sylvan - Highlands - Southwest Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Tides by the Sea

The Tides by the Sea

3 out of 5
Save 100% on your flight
Price was $384, price is now $223 per person
$223
per person
Jan 15 - Jan 18
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Portland (PDX)
7/10 Good! (2 reviews)
Black Walnut Inn & Vineyard

Black Walnut Inn & Vineyard

4 out of 5
Save 100% on your flight
Price was $1,691, price is now $946 per person
$946
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
10/10 Exceptional! (62 reviews)
Beautiful and Peaceful. Large room, wonderful sunrise views and amazing breakfasts. Friendly staff that respect your privacy and peace, so much that on a couple occasions I couldn’t find anyone. But if you want a quiet get away with a loved one, you’ll get it here.

Reviewed on Sep 26, 2025

Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
Price was $925, price is now $552 per person
$552
per person
Jan 11 - Jan 16
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
9.8/10 Exceptional! (85 reviews)
Extra Blankets that were provided were a life saver! Had a great stay while celebrating a birthday and our Honeymoon. 10/10 would love to come back.

Reviewed on Nov 22, 2025

Sentinel Hotel

Sentinel Hotel

5 out of 5
Downtown Portland
Save 100% on your flight
Price was $429, price is now $262 per person
$262
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
8.8/10 Excellent! (1,005 reviews)
Beautiful hotel. Staff was nice. No breakfast bar to speaf of, just coffee.

Reviewed on Oct 25, 2025

Columbia Gorge Hotel and Spa

Columbia Gorge Hotel and Spa

3.5 out of 5
Save 100% on your flight
Price was $367, price is now $231 per person
$231
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Portland (PDX)
9/10 Wonderful! (1,001 reviews)
A lovely find close to I84 and for travelers going to visit Mt Hood.. The hotel has an old world charm with staff operated elevators and particularly curated hallways and rooms. The Christmas decor was soft and comforting and the amazing piano at night elevated the experience. Add in the views from outside, and it makes for a place that I will definitely come back to

Reviewed on Dec 1, 2025

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Where to stay in Sylvan - Highlands - Southwest Hills

Find the best Sylvan - Highlands - Southwest Hills areas and neighborhoods for the activities you enjoy most. Learn more about Sylvan - Highlands - Southwest Hills
Downtown Portland - South Waterfront showing picnicing, boating and a bay or harbor

Downtown Portland

1 out of top 10 points of interest in this area
4.5/5(4,488 area reviews)

Explore the Portland Art Museum, Oregon Historical Society, and Tom McCall Waterfront Park in this central business district with high-rise buildings. Enjoy walkable streets, and easily access public transportation like MAX light rail and Portland Streetcar.

Find hotels in Downtown Portland

Sylvan - Highlands - Southwest Hills Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $110 total per night from Dec 21 to Dec 22
$110 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (3,058 reviews)
Yes

Reviewed on Dec 2, 2025

The Paramount Hotel
Embassy Suites by Hilton Portland Airport

Embassy Suites by Hilton Portland Airport

3.5 out of 5
7900 Ne 82nd Ave Portland OR
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Dec 11 to Dec 12
$129 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (2,088 reviews)
Room was spotless.

Reviewed on Dec 2, 2025

Embassy Suites by Hilton Portland Airport
Embassy Suites by Hilton Portland Downtown

Embassy Suites by Hilton Portland Downtown

4 out of 5
319 SW Pine St Portland OR
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $131 total per night from Dec 21 to Dec 22
$131 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,332 reviews)
Room was clean.. friendly staff will stay again

Reviewed on Nov 28, 2025

Embassy Suites by Hilton Portland Downtown
See all 2,819 properties in Sylvan - Highlands - Southwest Hills
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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Discover the most popular places to visit in Sylvan - Highlands - Southwest Hills

Moda Center

Moda Center

4.5/5(1,165 reviews)

See sporting teams do battle and rock out to musical legends at one of Portland’s major venues for sports and big-ticket entertainment events.

Moda Center
Oregon Convention Center

Oregon Convention Center

4.5/5(569 reviews)

Learn about the events happening at Oregon Convention Center during your trip to Portland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Oregon Convention Center
Oregon Zoo featuring zoo animals and landscape views as well as a large group of people

Oregon Zoo

4.5/5(610 reviews)

Awesome beasts native to America have a home alongside exotic and endangered species from around the world at this picturesque Portland attraction.

Oregon Zoo

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

$85
per traveler
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

$87
per adult
98% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Willamette River 2.5-hour Dinner Cruise

$127
per adult
96% of travellers recommend
Portland: Willamette River 2.5-hour Dinner Cruise
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.