Pleasant Valley Vacations from $402

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Your Pleasant Valley Vacation

Lock in a Pleasant Valley vacation package that includes everything you need without any unnecessary extras. Good for shopping, nightlife and bars and pubs, consider basing yourself in the neighborhood of Mississippi District. Fill up your itinerary with visits to Clackamas Town Center, Mt Hood Community College - Gresham Campus and Mall 205, some of the top attractions you really should see during your trip to Pleasant Valley. Stop dreaming and start adventuring. Browse the wide range of options on Expedia today and finally put your Pleasant Valley vacation plans in motion!

The Latest Pleasant Valley Vacation Packages

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

The Fireside Inn

$402
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Portland (PDX)
9.4/10 Exceptional! (920 reviews)
We arrived after hours and called the number left on the door. They were extremely helpful and sent a text with our sign in information and our passcode to get into our room. The room was quiet and clean and the bed comfortable. Nice place and I’d stay again!

Reviewed on Oct 7, 2026

The Grey Piper by Avantstay Ocean Views + Fire Pit + BBQ Walk to Beach

The Grey Piper by Avantstay Ocean Views + Fire Pit + BBQ Walk to Beach

Save 100% on your flight
$4,127
per person
Dec 27 - Jan 2
found 24 hours ago
Roundtrip flight included
Houston (HOU) to Portland (PDX)
No reviews
Portland's White House

Portland's White House

Northeast Portland
$687
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

Mark Spencer Hotel

Mark Spencer Hotel

Downtown Portland
$441
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (2,476 reviews)
Milwaukie Inn Portland South

Milwaukie Inn Portland South

Oak Grove
$493
per person
Dec 25 - Dec 30
found 5 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Portland (PDX)
7.6/10 Good! (602 reviews)

Where to stay in Pleasant Valley

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

Pleasant Valley Hotel Deals

Oxford Suites Portland - Jantzen Beach

Oxford Suites Portland - Jantzen Beach

12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
$114 nightly
$132 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,869 reviews)
"Great stay! The room was spacious, clean, comfortable, and quiet. Breakfast was delicious, and the staff were friendly. We appreciated the gated parking, with few additional parking outside. A car is recommended since the hotel is a little far from the main attractions. Overall, a pleasant stay!"

Reviewed on Oct 6, 2026

Oxford Suites Portland - Jantzen Beach
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

7101 NE 82nd Ave Portland OR
Fully refundableReserve now, pay when you stay
$96 nightly
$112 total
Oct 8 - Oct 9
Total with taxes and fees
Red Lion Hotel Portland Airport
Heathman Hotel

Heathman Hotel

1001 SW Broadway Portland OR
Fully refundableReserve now, pay when you stay
$141 nightly
$164 total
Oct 18 - Oct 19
Total with taxes and fees
9.2/10 Wonderful! (1,096 reviews)
"Hotel beautiful ~ staff very nice and accommodating. Location perfect for walking. Breakfast overpriced."

Reviewed on Oct 7, 2026

Heathman Hotel
See all 2,764 properties in Pleasant Valley
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.

Stay near popular Pleasant Valley attractions

Lakeside Gardens

Explore the lovely green spaces of Lakeside Gardens and also enjoy the biking trails in Portland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Leach Botanical Garden

Enjoy the beautiful waterfalls and explore Leach Botanical Garden, a lovely green space in Portland. Wander the riverfront and picturesque gardens in the area.
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Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

$88
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

$129
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
Picture 11 for Activity Portland: Champagne Brunch Cruise on Willamette River

Portland: Brunch Cruise on Willamette River

$105
per adult
92% of travellers recommend
Portland: Brunch Cruise on Willamette River
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.