A city skyline with illuminated buildings and a bridge over a calm river.

Jennings Lodge Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Jennings Lodge Vacation

Book a tailored Jennings Lodge vacation package that includes everything you need without any unnecessary extras. Good for shopping, nightlife and bars and pubs, think about staying in the neighborhood of Mississippi District. If taking in sights is on the to-do list during your trip to Jennings Lodge, visit popular attractions like Clackamas Town Center, Waverley Country Club and Milwaukie Farmers Market. Expedia has what you need to escape your daily routine. Tailor your vacation to Jennings Lodge to suit your style of travel, whatever that may look like.

The Latest Jennings Lodge Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 27 - Jan 2

    Portland Marriott Downtown Waterfront + Flight

    Downtown Portland
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,583
    CA $1,320
    per traveller
    found 1 day ago
    Portland Marriott Downtown Waterfront
  • Dec 27 - Jan 2

    Hotel Eastlund, BW Premier Collection + Flight

    Northeast Portland
    6 nights
    4.0 star property
    9.2/10 - Wonderful (2,265 reviews)
    "Great place to stay!"
    Reviewed November 14, 2026
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,655
    CA $1,348
    per traveller
    found 1 day ago
    Hotel Eastlund, BW Premier Collection
  • Dec 27 - Jan 2

    Mark Spencer Hotel + Flight

    Downtown Portland
    6 nights
    3.0 star property
    9.2/10 - Wonderful (2,565 reviews)
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,731
    CA $1,409
    per traveller
    found 1 day ago
    Mark Spencer Hotel
  • Dec 27 - Jan 2

    RiverPlace Hotel + Flight

    Downtown Portland
    6 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,883
    CA $1,533
    per traveller
    found 1 day ago
    RiverPlace Hotel
  • Dec 27 - Jan 2

    Hotel deLuxe + Flight

    Downtown Portland
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,164 reviews)
    "Perfect location!"
    Reviewed November 13, 2026
    Roundtrip • Toronto (YTO) - Portland (PDX)
    YYZ - PDX • 2 stops PDX - YYZ • 2 stops
    CA $1,805
    CA $1,493
    per traveller
    found 1 day ago
    Hotel deLuxe

Where to stay in Jennings Lodge

Find the best Jennings Lodge areas and neighborhoods for the activities you enjoy most.

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.

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.

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.

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!

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.

What to do near Jennings Lodge

Jennings Lodge Hotel Deals

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.

Frequently Asked Questions

How much does a Jennings Lodge vacation package cost?

Starting from as little as CA $1,320, you can tailor your Jennings Lodge package. Simply combine hotels, flights and car rentals and we'll reward you with discounts.

How do I get a cheap travel package to Jennings Lodge?

Think of all the awesome things you could do in Jennings Lodge with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your travel bookings into a Jennings Lodge vacation package. You have loads of choice when you book with Expedia too. In fact, you can pick from more than 550 air carriers and 1,000,000 hotels globally. Whether you're taking off with the family or surprising your special someone, planning a trip to Jennings Lodge is better with a package.

Where should I stay in Jennings Lodge?

If you'll be checking out Bike N Hike, save yourself the hassle of commuting and find a place to stay close by. It's one of the top attractions in this area.

What are the top hotels in Jennings Lodge?

Budget Inn Gladstone By OYO - Portland/Clackamas is one of Jennings Lodge's top properties. Reserve a room here and you can snooze soundly knowing you're in capable hands.

How far in advance should I book my Jennings Lodge vacation?

You'll be rewarded with the biggest variety at the lowest prices by booking your vacation to Jennings Lodge nice and early. Airlines typically sell flight tickets anywhere up to a year in advance, so start your planning as soon as possible. That being said, Expedia is constantly working to give you the best bargains around, so it's always a good time to book your dream vacation!

What does an Expedia Jennings Lodge travel package include?

Flights, rental cars and hotels — you'll find them all here. With Expedia, you can create your Jennings Lodge travel package the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the bigger your savings!

What should I know before booking a Jennings Lodge travel package?

So many places to explore, so many things to experience. With a package, you'll be able to cross more of them off your list. Bundle your hotels, rental cars and flights and land big savings.

Can I choose my airline with a Jennings Lodge Expedia vacation package?

Expedia offers access to more than 550 airline partners globally, so you certainly can. Just choose the airline you want and put together your ideal Jennings Lodge getaway.

If I'm not able to travel, can I cancel my Jennings Lodge vacation package?

We totally understand — unexpected stuff happens. If you've booked a Jennings Lodge vacation package and have to change or cancel it, we can help. It's always worth having a look at our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to change your itinerary for free. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.

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