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.
Ogunquit River Inn & Suites
Moody
CA $849
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We LOVED this property. The staff was BEYOND helpful and amazing. The rooms were clean. The beds were comfortable. The pool was perfect!
The property is BEAUTIFUL
Reviewed on Aug 10, 2026
Admiral Peary Inn
CA $908
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (55 reviews)
Had a wonderful one night stay at this property. Everything was spotless and top notch. Even walked into the common kitchen area to find fresh baked cookies for the guests.
Reviewed on Aug 7, 2026
Inn By The Sea
CA $1,426
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (327 reviews)
(+)
Location
Dog Friendly
Food
Parking
Everything you would expect from a luxury hotel - it is pricy.
Nothing negative.
Reviewed on Aug 2, 2026
AWOL Kennebunkport
CA $1,155
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (250 reviews)
Wonderful historic property updated with in-house suites & cabin-style lodgings. Adequate parking. Room was comfortable, new bathrooms & nice breakfast area. The breakfast itself was TDF!! The neighborhood is authentic. Walkable to downtown. Highly recommend.
Reviewed on Jul 20, 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.
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.
Parkside
While visiting Parkside, you might make a stop by sights like Fitzpatrick Stadium and Neal S. Dow House.
Downtown Portland Hotel Deals
Portland Regency Hotel & Spa
20 Milk Street Portland ME
CA $425
CA $471 total
Aug 30 - Aug 31
includes taxes & fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
CA $428
CA $527 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,805 reviews)
"A lovely historic hotel in the part of town with great restaurants and tourist attractions. Only valet parking is available, and to tip the valet you need to know their name as it is on line via a QR code! Beware technological luddites. As far as the hotel is concerned, we paid (modestly) extra for ..."
Reviewed on Aug 10, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
CA $354
CA $430 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (1,279 reviews)
"They advertised a rooftop bar but it wasn't what we expected and didn't have any view of the ocean room was large location was fair"
Reviewed on Aug 10, 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 Downtown Portland vacation package cost?
The most affordable Downtown Portland package is CA $849, 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.
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.
Wadsworth-Longfellow House
8.6/10 (119 reviews)
As you tour this historic brick home, trace three generations of Maine family history and learn about the cultural and political impact of its family members.
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 seaside or experience its acclaimed theater scene.
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 acclaimed theater scene.
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 acclaimed theater scene.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
90% of travellers recommend
Morning Lighthouse Cruise Along the Coast of Portland Maine
CA $83
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.