Old Port Vacations from $669
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Your Old Port Vacation
Planning your next adventure just got easier with a vacation package to Old Port. Take in the best this neighborhood has to offer while creating wonderful memories that will last forever. Wondering where to go during your trip to Old Port? Nearby attractions like Portland Museum of Art, University of Southern Maine and Victoria Mansion are excellent places to start. Stop daydreaming and start doing. When it's time to book your dream vacation to Old Port, Expedia is here to help.
The Latest Old Port Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Admiral Peary Inn
$809
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8.8/10 Excellent! (57 reviews)
Great place to stay, with any amenitie you can think of.
Should let seniors know that there is a steep set of stairs to the upper rooms.
Reviewed on Aug 27, 2026
The Meadowmere Resort
$758
per person
Oct 6 - Oct 10
found 4 hours ago
Roundtrip flight included
Denver (DEN) to Portland (PWM)
8.6/10 Excellent! (1,002 reviews)
Room was clean and staff was helpful but this is supposed to a good quality hotel yet it’s on the main road with lots of associated noice including morning garbage pickup, etc. Also this property has absolutely no view.
Reviewed on Aug 26, 2026
Where to stay in Old Port
Find the best Old Port areas and neighborhoods for the activities you enjoy most. Learn more about Old Port
Downtown Portland
4 out of top 10 points of interest in this area
Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.
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.
Old Port Hotel Deals
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$252 nightly
$278 total
Aug 30 - Aug 31
Total with taxes and fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$314 nightly
$348 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,832 reviews)
"The main issue with this hotel were the prices. $45 per day to park. $18 for an ordinary glass of wine. $6 for a piece of toast at breakfast. The wait staff was excellent though."
Reviewed on Aug 26, 2026
Canopy by Hilton Portland Waterfront
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
$382 nightly
$423 total
Aug 31 - Sep 1
Total with taxes and 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.
Stay near popular Old Port attractions
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.
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.
N.W. Barrett Gallery
You can spend time browsing the exhibits at N.W. Barrett Gallery during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Maine Sports Hall of Fame
You can spend an afternoon studying the exhibits at Maine Sports Hall of Fame during your travels in Portland. Stroll along the area's seaside or experience its acclaimed theater scene.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland Explorer: Boat Cruise with Oysters & Prosecco
$137
per adult
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- Two Lights State Park
- Spring Point Ledge Lighthouse
- Higgins Beach
- Fitzpatrick Stadium
- Visit Bailey Island
- East End Beach
- State Theatre
- Mclellan-Sweat House
- Downtown Portland Vacations
- Ll Bean Flagship Store
- International Cryptozoology Museum
- Maine Historical Society
- Merrill Auditorium
- Victoria Mansion
- Visit Old Port
- Fort Williams Park
- State Street Church
- Casco Bay Bridge
- Maine College of Art
- Port City Music Hall
- Visit Portland
- Eastern Promenade
- Mclellan-Sweat Mansion
- Fort Preble
- Maine Sports Hall of Fame
- Southworth Planetarium
- Bug Light
- Portland Head Light
- Maine Jewish Museum
- Wadsworth-Longfellow House
- Casco Bay Lines Ferry Terminal
- Charles Q. Clapp House
- Portland Museum of Art
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.