Portland Vacations from $374

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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.

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Chateau Resort & Conference Center

Chateau Resort & Conference Center

3 out of 5
Price was $406, price is now $374 per person
$374
per person
Sep 23 - Sep 25
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to Allentown (ABE)
7.4/10 Good! (1,049 reviews)
Hotel is old dirty and is in a desperate need of a renovation. I would never stay here again.

Reviewed on Jun 29, 2026

The Shawnee Inn and Golf Resort

The Shawnee Inn and Golf Resort

3 out of 5
Price was $631, price is now $476 per person
$476
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Allentown (ABE)
7.8/10 Good! (1,010 reviews)
Bartenders stunk. Food not so good. Golf great. Hotdogs great

Reviewed on Jun 26, 2026

Chestnuthill Countryside Manor

Chestnuthill Countryside Manor

2.5 out of 5
Price was $1,038, price is now $902 per person
$902
per person
Aug 24 - Aug 29
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Allentown (ABE)
9.6/10 Exceptional! (18 reviews)

Hillcrest Bed and Breakfast

Hillcrest Bed and Breakfast

2 out of 5
Price was $587, price is now $524 per person
$524
per person
Aug 24 - Aug 29
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Allentown (ABE)
No reviews
Hillcrest is up the hill a few minutes walk to downtown, in a very quiet area. The bedroom could use some updating - old curtains, drapes, bedspread, etc. - looks rundown. Bed was comfortable but room was very dusty. The house was just sold to a new owner, so the house is in transition. I do want to comment that the Innkeeper/B&B hosts that live on the property, Kyle and Christy Ann, (not the owners) are extremely nice and helpful.

Reviewed on Jun 29, 2026

Great Wolf Lodge Pocono Mountains, PA

Great Wolf Lodge Pocono Mountains, PA

3.5 out of 5
Price was $1,108, price is now $989 per person
$989
per person
Aug 24 - Aug 29
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Allentown (ABE)
8.4/10 Very Good! (1,011 reviews)
overall a great family experience, staff could be a little more knowledgeable with certain aspects of the hotel, but overall a good experience

Reviewed on Jun 29, 2026

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Portland Hotel Deals

Mount Airy Casino Resort - Adults Only 21+

Mount Airy Casino Resort - Adults Only 21+

4.5 out of 5
312 Woodland Road Mount Pocono PA
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $199 total per night from Jul 1 to Jul 2
$199 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (3,072 reviews)
"Perfect mini vaca"

Reviewed on Jun 30, 2026

Mount Airy Casino Resort - Adults Only 21+
Camelback Resort

Camelback Resort

3.5 out of 5
193 Resort Drive Tannersville PA
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $245 total per night from Jul 23 to Jul 24
$245 total
Jul 23 - Jul 24
Total with taxes and fees
8.2/10 Very Good! (2,744 reviews)
"I didn’t like that they don’t clean the rooms everyday. Breakfast it’s not included, we had to pay for every meal. It is a family friendly space and the indoor waterpark wasn’t bad."

Reviewed on Jun 30, 2026

Camelback Resort
Great Wolf Lodge Pocono Mountains, PA

Great Wolf Lodge Pocono Mountains, PA

3.5 out of 5
1 Great Wolf Dr Scotrun PA
$183 nightly
The price is $199 total per night from Jul 15 to Jul 16
$199 total
Jul 15 - Jul 16
Total with taxes and fees
8.4/10 Very Good! (1,018 reviews)
"overall a great family experience, staff could be a little more knowledgeable with certain aspects of the hotel, but overall a good experience"

Reviewed on Jun 29, 2026

Great Wolf Lodge Pocono Mountains, PA
See all 1,374 properties in Portland
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.

Find the Best Portland Vacation Packages

Portland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lehigh Valley Intl. Airport (ABE)
Population
510
Top Sights
Shawnee Mountain Ski Area, Sherman Theater and Smithfield Beach National Recreation Area

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Frequently asked questions

How much does a Portland vacation package cost?
You can snap up a vacation package to this destination from $374 on Expedia. However, how much your vacation to Portland costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Portland?
November, December and January are the best times to search for cheap Portland vacation packages. Opting to travel in quieter months means you'll typically find lower prices on accommodations and flights.
How many days is enough for Portland?
The ideal duration for your Portland vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to visit all the top attractions and explore some hidden spots along the way.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Portland package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Portland adventure off to a flying start.
Is it cheaper to book a Portland vacation as a package?
You can enjoy significant savings on your next Portland break by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Portland?
Land incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Portland getaway.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Your Portland trip should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.