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 $800

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (2,405 reviews)

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland

CA $956

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (1,008 reviews)

Great

Reviewed on Sep 1, 2026

The Independence

CA $1,062

per person

Oct 19 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PDX)

9.6/10 Exceptional! (1,016 reviews)

The Tides by the Sea

CA $1,673

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PDX)

8.6/10 Excellent! (52 reviews)

The Spinn

CA $1,149

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PDX)

9.2/10 Wonderful! (86 reviews)

Great location and very nice rooms

Reviewed on Sep 1, 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

2 out of top 10 points of interest in this area

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 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 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 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

2 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

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $130

CA $151 total

Sep 2 - Sep 3

includes taxes & fees

DoubleTree by Hilton Hotel Portland

1000 NE Multnomah Street Portland OR

Fully refundableReserve now, pay when you stay

CA $169

CA $197 total

Sep 13 - Sep 14

includes taxes & fees

8.6/10 Excellent! (1,221 reviews)

"Very nice clean friendly place to stay. We will come again"

Reviewed on Sep 1, 2026

Country Inn & Suites by Radisson, Portland International Airport, OR

7025 NE Alderwood Rd Portland OR

Fully refundable

CA $154

CA $180 total

Oct 1 - Oct 2

includes taxes & fees

See all 2,833 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.