Portland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Portland Vacation
Entertainment, history, art and more … There's so much to immerse yourself in with a Portland vacation package. And with the ability to easily customize your city getaway, it's guaranteed to be one that's tough to forget. Every trip to Portland needs a well-thought-out itinerary. Fill yours with major attractions like Shawnee Golf Resort, Lakota Wolf Preserve and Pocono Snake and Animal Farm. Expedia is here to help you escape your routine. Tailor your vacation to Portland to suit your travel style, whatever that may look like.
Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chateau Resort & Conference Center
CA $787
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Allentown (ABE)
7.4/10 Good! (1,085 reviews)
Property is definitely outdated. My room was right next to the elevator so I didn’t sleep well with all the noise.
Reviewed on Sep 6, 2026
Ready to book your vacation to Portland?
Portland Hotel Deals
Mount Airy Casino Resort - Adults Only 21+
312 Woodland Road Mount Pocono PA
Fully refundableReserve now, pay when you stay
CA $159
CA $225 total
Sep 8 - Sep 9
includes taxes & fees
9/10 Wonderful! (3,261 reviews)
"We loved our three night stay! Everything and everyone was above and beyond! Played golf next door at the Mount Airy GC... incredible shape, well maintained and beautiful!!! Not gamblers, so no idea what that is all about."
Reviewed on Sep 6, 2026
The Swiftwater
2060 Pennsylvania 611 Swiftwater PA
Fully refundableReserve now, pay when you stay
CA $255
CA $278 total
Sep 27 - Sep 28
includes taxes & fees
Great Wolf Lodge Pocono Mountains, PA
1 Great Wolf Dr Scotrun PA
CA $282
CA $307 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (1,139 reviews)
"Friendly staff"
Reviewed on Sep 6, 2026
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 Portland vacation package cost?
Offering excellent value package deals from CA $787 on Expedia, you'll be surprised at how little a vacation to Portland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Portland?
January, February and March are great times to search for cheap Portland vacation packages. Opting to travel in less busy periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Portland?
Generally, a few days is ideal for a Portland vacation. With a carefully crafted itinerary, you can visit all the main sights such as Brook Hollow Winery, as well as explore some hidden gems along the way.
How to find the best Portland package deals?
Finding a cheap Portland package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Portland package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Portland getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Portland?
If you're considering a spontaneous Portland vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Portland?
- Pick your travel dates: The things you plan to do in Portland and your preferred season can help you decide when to get away.
- Work out your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Portland.
- Set the duration of your trip: Start by listing all the sights and activities you want to get to in Portland. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Portland vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
