Downtown Portland Vacation Packages
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Top Holiday Package Deals in Downtown Portland
Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit
CA $951
per person
Oct 11 - Oct 16
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (408 reviews)
Every year we go there, its convenient to town and clean. The only thing is i wish the shuttle took you down to Perkins cove.
Reviewed on Aug 28, 2026
The Kennebunk Inn
CA $967
per person
Oct 11 - Oct 16
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8/10 Very good! (788 reviews)
Cozy place to stay with a great location and friendly staff. The tavern was so fun too! The beds were very firm for those who have bad backs but beside that I would stay again!
Reviewed on Sep 6, 2026
Where to stay in Downtown Portland
Find the best Downtown Portland areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Portland
Old Port
Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.
West End
Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
Parkside
While visiting Parkside, you might make a stop by sights like Fitzpatrick Stadium and Neal S. Dow House.
East Bayside
Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.
Downtown Portland Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
CA $499
CA $605 total
Sep 10 - Sep 11
includes taxes & fees
9.2/10 Wonderful! (1,831 reviews)
"Staff was great, but rooms and amenities were incredibly dated. The bathroom had no ventilation, a very old shower, and mediocre product options. The rooms were very bare bones and not warm or inviting. There was nothing all that special about this property and certainty not worth the nightly ..."
Reviewed on Sep 6, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
CA $351
CA $388 total
Sep 20 - Sep 21
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Great lication, clean, nice hotel."
Reviewed on Sep 8, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
CA $400
CA $480 total
Sep 20 - Sep 21
includes taxes & fees
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 Downtown Portland vacation package cost?
The most affordable Downtown Portland package is CA $951, so your dream escape can become a reality — without spending a fortune. Combine flights, hotels and car rentals to build a package that fits you.
How do I get a cheap travel package to Downtown Portland?
Bundle your flights and hotels, add on extras such as tours, and save with a Downtown Portland vacation package. You won't just walk away with impressive discounts on your adventure — you'll have plenty of choice too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 properties globally. Your next epic adventure begins right here, right now!
Where should I stay in Downtown Portland?
Take the leg work out of sightseeing by staying right around the corner from Downtown Portland's big attractions. University of Southern Maine and Portland Museum of Art are two of the best in this neighborhood.
What are the top hotels in Downtown Portland?
Make a reservation at The Docents Collection. It's one of the neighborhood's most sought-after properties. Another highly rated option in Downtown Portland is Canopy by Hilton Portland Waterfront.
How far in advance should I book my Downtown Portland vacation?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you're unable to do so, don't worry. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Downtown Portland travel package include?
You can select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's also possible. The choice is yours when it comes to putting together your dream Downtown Portland getaway.
What should I know before booking a Downtown Portland travel package?
Our prices are always low. However, you'll snap up even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Downtown Portland Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're in control. We have more than 550 airline partners around the world, so you have lots of choice when arranging your Downtown Portland trip.
If I'm not able to travel, can I cancel my Downtown Portland vacation package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Downtown Portland vacation package at no cost within 24 hours of booking. For bookings older than that, you can still make changes, but your hotel, car rental company or airline may impose a charge. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
Stay near popular Downtown Portland attractions
State Theatre
8.8/10 (392 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
9.2/10 (610 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Photo by Tim Thomas
Maine College of Art
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's acclaimed theater scene and great live music.
State Street Church
Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
Merrill Auditorium
8.8/10 (107 reviews)
You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Fore Street Gallery
You can spend an afternoon studying the exhibits at Fore Street Gallery during your trip to Portland. Experience the area's entertainment choices and great live music.
International Cryptozoology Museum
You can spend time browsing the exhibits at International Cryptozoology Museum in Portland. Stroll along the area's waterfront or experience its great live music.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $107
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $82
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.