Crestwood Vacations from $337

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Your Crestwood Vacation

Lock in a Crestwood vacation package and prepare to experience the highlights of this city. Consider staying in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining. Make your trip to Crestwood even more fun and exciting by including some sightseeing. Oregon Zoo, Portland State University and Portland Japanese Garden are some of the most popular attractions you'll want to explore. Whoever you're going away with and whatever your bank balance, your dream Crestwood vacation is just clicks away with Expedia.

The Latest Crestwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a bed, a desk, a chair, a television, and a ceiling fan.
    Jan 8 - Jan 11

    Capitol Hill Motel + Flight

    Southwest Portland
    3 nights
    2.5 star property
    9.2/10 - Wonderful (876 reviews)
    Roundtrip • Los Angeles (QLA) - Portland (PDX)
    LAX - PDX • Nonstop PDX - LGB • 1 stop
    $458
    $337
    per traveler
    found 1 day ago
    Capitol Hill Motel
  • A modern dining area with brick walls, large windows, and a wooden bench.
    Dec 17 - Dec 23

    Mark Spencer Hotel + Flight

    Downtown Portland
    6 nights
    3.0 star property
    9.2/10 - Wonderful (2,534 reviews)
    "Great hotel The lobby has more of an olde timey hotel feel which not everyone will like, but the rooms are great and the staff are friendly and helpful It had all the key things I want when I travel Bed - Ultra comfy - I’m picky, and it was brilliant Blackout curtains - Effective Shower - fantastic - plenty of heat available when you want it, great pressure and shower head Aircon - excellent - effective and not noisy Location - close to the light rail stop etc - walking distance to..."
    Reviewed November 4, 2026
    Roundtrip • Burbank (BUR) - Portland (PDX)
    BUR - PDX • Nonstop PDX - BUR • Nonstop
    Save 100% on your flight
    $789
    $516
    per traveler
    found 1 day ago
    Mark Spencer Hotel
  • A modern lounge area with two green leather sofas, a wooden coffee table, and a bar area with a teal accent wall.
    Jan 8 - Jan 12

    The Dundee - A Trace Hotel + Flight

    Dundee
    4 nights
    2.0 star property
    10/10 - Exceptional (94 reviews)
    Roundtrip • San Diego (SAN) - Portland (PDX)
    SAN - PDX • Nonstop PDX - SAN • Nonstop
    Save 100% on your flight
    $571
    $402
    per traveler
    found 15 hours ago
    The Dundee - A Trace Hotel
  • A large, illuminated hotel with a prominent central building and a boat docked nearby.
    Dec 17 - Dec 23

    RiverPlace Hotel + Flight

    Downtown Portland
    6 nights
    4.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip • Burbank (BUR) - Portland (PDX)
    BUR - PDX • Nonstop PDX - BUR • Nonstop
    Save 100% on your flight
    $954
    $693
    per traveler
    found 1 day ago
    RiverPlace Hotel
  • A living room with a blue sofa, a wooden coffee table, a fireplace, and a ceiling fan.
    Jan 16 - Jan 20

    The Morehead by Stay Portland - Nob Hill + Flight

    Northwest Portland
    4 nights
    2.0 star property
    10/10 - Exceptional (1 review)
    "Great location and lots of space. A little bit of dirty left from the past guests and a locked door to the upstairs which we were told the other guests would not have access to, it just surprised us at first. Nicely styled apartment with well stocked (with basics) kitchen. Overall was a great stay!"
    Reviewed September 23, 2026
    Roundtrip • Dallas (DFW) - Portland (PDX)
    DFW - PDX • Nonstop PDX - DFW • Nonstop
    $1,240
    $913
    per traveler
    found 22 hours ago
    The Morehead by Stay Portland - Nob Hill

Where to stay in Crestwood

Find the best Crestwood areas and neighborhoods for the activities you enjoy most.
A theater marquee with 'Portland' and 'An Evening with Crosby, Stills & Nash' written on it.

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.

The Moda Center with a clear sky, trees, and a pedestrian area.

Northeast Portland

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 large industrial building with a prominent red chimney and the letters "QMS" on its side.

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

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.