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Portland, OR vacations

Experience all that Portland, Oregon has to offer with a flight, hotel, and car rental package from Southwest Vacations®.
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Here are a few of our most popular Portland resorts:

  • TripAdvisor traveler rating
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    Portland, OR


    Crowne Plaza Portland Downtown - Convention Center is a great place to base your next trip to Portland.

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    Portland, OR

    The Nines a Luxury Collection Hotel Portland

    Ideally situated next to Portland’s Pioneer Square and the MAX light Rail.

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    Portland, OR

    The Westin Portland

    A boutique-style hotel in the heart of downtown, ideal for recharging.

Things to do in Portland, OR

  • Skyscraper

    Downtown Portland and City Highlights Tour

    Enjoy a private, informative and interactive downtown Portland and city highlights tour. See the top, can't-be-missed highlights and attractions that the city has to offer.
  • Mount St. Helens National Volcanic Monument

    Mount Saint Helens Tour

    Go on a 10-hour excursion from Portland to Mt. St. Helens (Loowit according to one native tribe). Through hikes, viewpoints, and stories, get intimate with the area around Mt. St. Helens. Snacks and water are provided, and there is a stop for lunch and drinks.
  • Oregon gardens silverton

    Falls, Gardens, and Wine Tour

    A trip to and from the scenic Willamette Valley starts and concludes your day. Stops include a farm, gardens, several waterfalls and wine tasting.

Family activities in Portland, OR

  • The Portland Underground/Shanghai Tunnels

    The Old Portland Underground is a series of subterranean tunnels or passageways, in Portland, mainly under Old Town Chinatown, that connect to the central business section of downtown. Creating a labyrinth connecting hotel basements and taverns to the Willamette River waterfront. Originally used to move goods from the docks of the Willamette to basement storage facilities curbing street congestion and conflict with trains and streetcar routes. "Shanghai Tunnels" comes from urban legends that they were used by organized crime and others to "shanghai" (kidnap) sailors. However, you can book a Portland vacation package with Southwest Vacations of your choosing, no shanghaiing allowed!
  • OMSI

    O.M.S.I., as it is locally known, is the Oregon Museum of Science and Industry. The museum focuses on science and technology. The Portland museum has three large auditoriums: a planetarium, an exhibition hall, and a large-screen theater. Permanent Hands-on exhibits revolve around the natural sciences, industry, and technology. Other traveling or temporary exhibits round out the museum's features and cover a wider range of subjects. The interactive nature of the exhibits delight kids and keep locals coming back frequently.
  • The Oregon Rail Heritage Center

    Why are kids fascinated with trains? This Portland railway museum may have that answer or more. The City of Portland owns three steam locomotives on permanent display: the Oregon Railroad & Navigation Co. 197, the Southern Pacific 4449, and the Spokane, Portland & Seattle 700. The 4449 and the 700 are restored and fully operational. The center rotates other train stock and exhibitions throughout the year. The O.R.H.F.'s purpose is the preserve, educate, and celebrate the railroading history of Oregon. Get up close and personal with these industrial-age historic machines!

Nightlife and entertainment in Portland, OR

  • Fine dining

    Considering the eclectic and creative reputation, the City of Portland has it should come as no surprise that this creativity and variety translates to the cities culinary scene. Portland is host to many, many breweries, coffeehouses, exceptional restaurants, carts, trucks, and markets. Suggested standouts your vacation dining itinerary should include are Ichiza Kitchen, Jaqueline, Nimblefish, Smokin Fire Fish, Stretch the Noodle, and The Sundra. One MUST visit Voodoo Doughnut, for hopefully obvious reasons.
  • Club/dancing

    Jones Night Club, Dirty, The Barrel Room, the list goes on. One might equate the Pacific NW with live rock music, including grunge and punk, but Portland has a thumping club scene. Holocene has themed dance nights several times a week with recurring nights like Emo Night, Snap!, and Dance Yourself Clean. The Lovecraft is for the goth/industrial and spins dark danceable tunes from new wave, no-wave, coldwave, and post-punk bands. Goodfoot hosts Soul Stew an all-vinyl soul dance party. R.E.S.P.E.C.T.
  • Portland Brewery Bike Tour

    Beers and bikes! Not an entirely new concept but for sure a fun one. Portland has a world-famous beer culture, and what better way to experience and enjoy it than with a group of like-minded individuals all pedaling with a common purpose: More Beer! Pedal off the calories as you get to tour the city and visit top-notch microbreweries like Deschutes, Rogue, Bridgeport, and Lucky Lab. Explore Downtown Portland, the Pearl District, and N.W. Portland while making new friends and discover new favorite beers.

Experience all that Portland, Oregon has to offer with a flight, hotel, and car rental package from Southwest Vacations. Considered the most environmentally "green" city in the United States, Portland offers families and active travelers a wealth of dining and entertainment, lovely parks and gardens, and a variety of museums and attractions. Book everything you need for a Portland vacation today and experience first hand the contagious appeal of this Pacific Northwestern cityscape.