Overlook Vacations from $205

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Your Overlook Vacation

Book a tailored Overlook vacation package that includes everything you need without any unnecessary extras. Good for shopping, nightlife and bars and pubs, consider staying in the neighborhood of Mississippi District. Ready to get out and explore? Oregon Zoo, Portland State University and Portland Japanese Garden are a few of the top places to visit during your trip to Overlook. Your perfect Overlook vacation is clicks away. Search airfares, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Overlook Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Shilo Inn Suites Hotel - Warrenton

Shilo Inn Suites Hotel - Warrenton

2.5 out of 5
Save 100% on your flight
Price was $314, price is now $205 per person
$205
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Portland (PDX)
7.4/10 Good! (1,000 reviews)
It was good except the hot tub was broken

Reviewed on Dec 1, 2025

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

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 1 day ago
Roundtrip flight included
Phoenix (PHX) to Portland (PDX)
7/10 Good! (2 reviews)
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 20 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

Seagull Beachfront Inn

Seagull Beachfront Inn

3 out of 5
Oceanlake
Save 100% on your flight
Price was $613, price is now $376 per person
$376
per person
Feb 13 - Feb 17
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
7.6/10 Good! (861 reviews)
Lovely stay. The woman at the desk was very nice. Our room was very comfortable. The hot tub is just what we needed after hiking for several day. And the view was the best. Thank you

Reviewed on Nov 30, 2025

Where to stay in Overlook

Find the best Overlook areas and neighborhoods for the activities you enjoy most. Learn more about Overlook
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

Overlook 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 10 to Dec 11
$129 total
Dec 10 - Dec 11
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 2,800 properties in Overlook
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Overlook

Swan Island

Swan Island

You can find out about the history of Portland when you stop by Swan Island. Stroll along the riverfront or visit the shops in the area.

Swan Island

Overlook Park

After visiting Overlook Park, make a plan to see the other sights and activities in Portland. Stroll along the area's riverfront or experience its great live music.

Overlook Park

Interstate Firehouse Cultural Center

After visiting Interstate Firehouse Cultural Center, make a plan to see the other sights and activities in Portland. Wander the riverfront and picturesque gardens in the area.

Interstate Firehouse Cultural Center

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.