Old Port Vacations from $703
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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.
Nautical Mile
$703
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
Blind Tiger Portland - Danforth Street.
West End
$1,094
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Wonderful staff, convenient location, fun stay in an old building. So much character with modern amenities and a neighborhood feel. We thoroughly enjoyed our stay and will return. Off-street parking was a huge bonus and the light breakfast had a wide spread. Such a wonderful property.
Reviewed on Oct 11, 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
5 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.
West Bayside
If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.
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.
Old Port Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$181 nightly
$201 total
Nov 1 - Nov 2
Total with taxes and fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$155 nightly
$172 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (1,768 reviews)
"The good - The valet was excellent. Warm greeting, took our car, brought up our luggage asap. - Check-in was easy - Room was averagely spacious - Can't beat the location - The Armory was good, Had two drinks and the waitress was very nice. The bad - This place is dated and somewhat dilapidated. No ..."
Reviewed on Oct 11, 2026
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
$122 nightly
$135 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Great view of the waterfront"
Reviewed on Oct 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.
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 great live music.
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 great live music.
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 great live music.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
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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.