Overlook Vacations from $225

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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
Price was $307, price is now $225 per person
$225
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
9/10 Wonderful! (1,005 reviews)
Tired hotel. Missing detail that we usually enjoy in hotels of this star

Reviewed on Sep 20, 2025

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $459, price is now $252 per person
$252
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
9.2/10 Wonderful! (1,734 reviews)
The hotel is older, when we got to our room, the room was not cleaned. It was stains everywhere and the room had a smell. We ended up moving to another room, that one was a little better. The staff were nice and kind. It’s extremely noisy, but that’s expected staying on a main street.

Reviewed on Oct 12, 2025

Packwood Inn

Packwood Inn

2.5 out of 5
Save 100% on your flight
Price was $523, price is now $354 per person
$354
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
7.6/10 Good! (494 reviews)
Older property. No hairdryer. Frig was loud and so was other people in adjoining rooms. Maybe needs better soundproofing?

Reviewed on Oct 8, 2025

Hotel Lucia

Hotel Lucia

4 out of 5
Downtown Portland
Price was $526, price is now $365 per person
$365
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
9.2/10 Wonderful! (1,225 reviews)
Friendly staff | clean room | conveniently located

Reviewed on Oct 9, 2025

Dossier Hotel

Dossier Hotel

4.5 out of 5
Downtown Portland
Price was $456, price is now $331 per person
$331
per person
Dec 6 - Dec 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PDX)
9.4/10 Exceptional! (1,218 reviews)
The hotel was clean. It was very cold in our room. The heater did not work. When we called the front desk, they have gave us extra blankets but they were thin, itchy, and not something I wanted on my body. They looked like something you would find in an attic. I was very disappointed. We literally slept in sweatshirts. The second night I asked for front desk to charge my Tesla. Woke up the next morning and my car was not charged. This is a service they offer and it was not fulfilled as promised. I would not stay here again.

Reviewed on Oct 13, 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

The Palms Motel

The Palms Motel

2 out of 5
3801 N Interstate Ave, Portland, OR
Fully refundable
$69 nightly
The price is $80 total per night from Oct 20 to Oct 21
$80 total
Oct 20 - Oct 21
Total with taxes and fees
7/10 Good! (15 reviews)
"really good"

Reviewed on Oct 10, 2025

The Palms Motel
Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
$67 nightly
The price is $78 total per night from Oct 19 to Oct 20
$78 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (2,674 reviews)
"Quick shuttle ride was nice after a late flight. Holiday Inn was fantastic."

Reviewed on Oct 12, 2025

Holiday Inn Airport - Portland by IHG
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Oct 20 to Oct 21
$118 total
Oct 20 - Oct 21
Total with taxes and fees
8.6/10 Excellent! (2,128 reviews)
"Great space and price for a short stay"

Reviewed on Oct 12, 2025

Courtyard by Marriott Portland City Center
See all 2,754 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 great live music.

Historic Overlook House

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.