Overlook Vacations from $284

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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.
Kimpton Hotel Vintage Portland by IHG

Kimpton Hotel Vintage Portland by IHG

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $478, price is now $284 per person
$284
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9/10 Wonderful! (1,000 reviews)
The place was very understaffed, but all the staff was very excellent. They always accommodated any requests I made and overall it was a very nice stay worth the price.

Reviewed on Aug 15, 2025

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $671, price is now $375 per person
$375
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,667 reviews)
We were in town from SoCal helping a family member out during a very difficult time. The hotel location and property were great. The best part of the stay was definitely the service from Timmy at the front desk. I looked forward to returning to my room every evening, with hopes that he'd be there at the desk to encourage me to come get happy hour drinks. It was a much needed distraction and act of kindness to offset a sad and stressful time.

Reviewed on Aug 27, 2025

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Save 100% on your flight
Price was $779, price is now $484 per person
$484
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9/10 Wonderful! (1,000 reviews)
Beautiful hotel, friendly staff. Unfortunately area around hotel has a lot of homeless people shouting and it felt a bit unsafe after dark.

Reviewed on Aug 17, 2025

Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
Price was $717, price is now $449 per person
$449
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PDX)
9.8/10 Exceptional! (55 reviews)
The views were amazing! Also, Zack was so welcoming and made us feel comfortable.

Reviewed on Aug 20, 2025

Hotel Lucia

Hotel Lucia

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $534, price is now $336 per person
$336
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,219 reviews)
Older hotel, renovated in very hip style. Seems to appeal to a younger crowd.

Reviewed on Aug 20, 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

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

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
1000 NE Multnomah Street, Portland, OR
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Sep 3 to Sep 4
$138 total
Sep 3 - Sep 4
Total with taxes and fees
8.2/10 Very Good! (1,013 reviews)
"We enjoyed our stay and went to a concert."

Reviewed on Aug 25, 2025

DoubleTree by Hilton Hotel Portland
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
$119 nightly
The price is $138 total per night from Sep 3 to Sep 4
$138 total
Sep 3 - Sep 4
Total with taxes and fees
8.6/10 Excellent! (1,951 reviews)
"No issues with the hotel. Unfortunately Downtown Portland is filled with homeless people and drug use."

Reviewed on Aug 23, 2025

Courtyard by Marriott Portland City Center
The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Sep 22 to Sep 23
$121 total
Sep 22 - Sep 23
Total with taxes and fees
9.2/10 Wonderful! (2,730 reviews)
"a nice hotel, friendly staff, a lot of homeless people nearby, difficult to find day parking"

Reviewed on Aug 25, 2025

The Paramount Hotel
See all 2,708 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

Patton Square Park

Patton Square Park is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Wander around the area's picturesque gardens or experience its acclaimed theater scene.

Patton Square Park

Historic Overlook House

You can find out about the history of Portland with a trip to Historic Overlook House. Stroll along the area's riverfront or experience its acclaimed art scene.

Historic Overlook House

Things to do

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
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 Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$7
per adult
Downtown Golden Adventure Quest Experience in Portland
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.