Uplands Vacation Packages

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Top Holiday Package Deals in Uplands

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

Hood River Hotel

CA $688

per person

Oct 26 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

9/10 Wonderful! (1,006 reviews)

Clean and cozy, and kind staff.

Reviewed on Sep 23, 2026

Inn of the White Salmon

CA $773

per person

Oct 26 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PDX)

9.4/10 Exceptional! (113 reviews)

Very small, quiet room, tiny bath, nice shower, bed ok but too soft for me, awkward bedside lamp switches, lovely, very quiet, outdoor lounge/garden areas, really cute quiet, friendly town. Price was right.

Reviewed on Sep 18, 2026

Darlingwood

CA $902

per person

Nov 5 - Nov 8

found 14 hours ago

Roundtrip non-stop flight included

Detroit (DTT) to Portland (PDX)

9.6/10 Exceptional! (4 reviews)

The setting is tranquil, with beautiful views, and the home itself is lovely. Our host was welcoming and gracious. The B&B is about two miles down gravel roads with fairly deep washboards, so guests should be prepared for a rough drive. We love staying at true bed and breakfasts, and for us, part of the charm is the experience of a thoughtfully prepared, homemade breakfast. Unfortunately, the breakfast we received was a bit disappointing—a scone, two strawberries, and five blueberries left us wanting more. In fairness, the fault is partly ours for not having more realistic expectations about what was included. The property and setting are beautiful, and the host was very welcoming, but the breakfast experience did not live up to what we typically expect from a bed and breakfast.

Reviewed on Aug 10, 2026

Heathman Hotel

Downtown Portland

CA $977

per person

Nov 5 - Nov 8

found 14 hours ago

Roundtrip non-stop flight included

Detroit (DTT) to Portland (PDX)

9.2/10 Wonderful! (1,091 reviews)

Excellent location, and wonderful vibe.

Reviewed on Sep 25, 2026

Jupiter NEXT

Southeast Portland

CA $977

per person

Nov 19 - Nov 22

found 6 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

9.2/10 Wonderful! (708 reviews)

Where to stay in Uplands

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

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

Downtown Portland

1 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 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

1 out of top 10 points of interest in this area

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

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.

Uplands Hotel Deals

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $167

CA $194 total

Oct 14 - Oct 15

includes taxes & fees

9.2/10 Wonderful! (3,720 reviews)

"The room was tidy and bright. We had an issue with the mini-fridge not working and they replaced it as soon as we called the front desk about it. They were very attentive!"

Reviewed on Sep 26, 2026

Heathman Hotel

1001 SW Broadway Portland OR

Fully refundableReserve now, pay when you stay

CA $142

CA $213 total

Oct 18 - Oct 19

includes taxes & fees

9.2/10 Wonderful! (1,084 reviews)

"Excellent location, and wonderful vibe."

Reviewed on Sep 25, 2026

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

7025 NE Alderwood Rd Portland OR

Fully refundable

CA $143

CA $167 total

Oct 27 - Oct 28

includes taxes & fees

8.8/10 Excellent! (3,253 reviews)

"This place was a dump. Save your money and go elsewhere."

Reviewed on Sep 25, 2026

See all 2,861 properties in Uplands

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.