Highland Vacation Packages

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Top Holiday Package Deals in Highland

Price found within the past 48 hours. Click for updated prices.

Mark Spencer Hotel

Downtown Portland

CA $700

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

9.2/10 Wonderful! (2,476 reviews)

Timmy checked us in and was very friendly and helpful.

Reviewed on Oct 17, 2026

Hotel deLuxe

Downtown Portland

CA $782

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

8.6/10 Excellent! (1,135 reviews)

The Hotel Zags Portland

Downtown Portland

CA $724

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

8.6/10 Excellent! (1,236 reviews)

Reviewed on Oct 18, 2026

Portland's White House

Northeast Portland

CA $1,466

per person

Jan 6 - Jan 10

found 3 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Portland (PDX)

10/10 Exceptional! (1 review)

Such a great stay, warm and welcoming host. I only had one issue and the host took care of it immediately. The breakfast was amazing and the coffee was hot which was huge for me. My first B&B stay but definitely not my last.

Reviewed on Sep 27, 2026

Park Lane Suites and Inn

Southwest Portland

CA $736

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

8.6/10 Excellent! (1,966 reviews)

Great place stayed for the weekend they were able to check us in a little earlier

Reviewed on Oct 18, 2026

Where to stay in Highland

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

Two people sitting on a blanket by a marina with boats docked in the background.

Downtown Portland

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.

A forested area with a stone structure, wooden benches, and a pathway leading to a central point.

Northeast Portland

1 out of top 10 points of interest in this area

Inner Northeast Portland boasts shopping areas like Lloyd District and Alberta Arts District, while the area near Burnside Bridge offers a lively nightlife with bars such as The Chesterfield and music venues like The Doug Fir Lounge.

A street with a modern building featuring large murals, parked cars, and a café with outdoor seating.

Pearl District

Discover art galleries like Elizabeth Leach Gallery, dine at diverse restaurants, and unwind in public plazas such as Jamison Square. Easily navigate with the Portland Streetcar and explore nearby iconic Powell's City of Books.

A dinosaur statue in front of a building with a glass facade and the letters 'OMS' on it.

Southeast Portland

Stretching from the Willamette River to Gresham, Southeast Portland boasts the scenic Mt. Tabor Park and the quirky Hawthorne district with its subculturally oriented shops. Don't miss exploring Reed College campus!

A cable car system, a cityscape with high-rise buildings, a river, and a mountain in the background.

Southwest Portland

3 out of top 10 points of interest in this area

Downtown Portland boasts cultural, educational, and retail hotspots, with attractions like Tom McCall Waterfront Park, Portland Art Museum, and Pioneer Place mall. Enjoy pedestrian-friendly streets and unique residential areas in Southwest Portland.

Highland Hotel Deals

Oxford Suites Portland - Jantzen Beach

12226 N JANTZEN DRIVE Portland OR

Fully refundableReserve now, pay when you stay

CA $123

CA $159 total

Nov 1 - Nov 2

includes taxes & fees

9/10 Wonderful! (1,912 reviews)

"We stayed there for 3 days. The staff at the bar where we were supposed to get our "free" drinks, was rude. It took me 3 times to get my "free" drink because she was so unhelpful. Then the soup that they served was discusting, watery mushy vegetables. The "secure" gate to the parking lot was broken ..."

Reviewed on Oct 18, 2026

Red Lion Hotel Portland Airport

7101 NE 82nd Ave Portland OR

Fully refundableReserve now, pay when you stay

CA $115

CA $134 total

Nov 1 - Nov 2

includes taxes & fees

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $139

CA $162 total

Nov 15 - Nov 16

includes taxes & fees

See all 2,843 properties in Highland

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.