Old Port Vacations from $680
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
$680
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.6/10 Excellent! (24 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
The Francis
Parkside
$942
per person
Oct 29 - Nov 1
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.4/10 Exceptional! (406 reviews)
Very pleasant and attentive staff, nice location and easy free-parking options. But the room was too small to contain a couple of large suitcases, and the mini fridge was so packed with minibar items that you couldn’t fit in one bottle of water. Being on the ground floor, we could hear the steps of the people in the room above us. Good, nice, but that’s it.
Reviewed on Sep 24, 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.
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 Neal S. Dow House and Fitzpatrick Stadium.
Old Port Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
$277 nightly
$306 total
Oct 25 - Oct 26
Total with taxes and fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
$210 nightly
$232 total
Oct 26 - Oct 27
Total with taxes and fees
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
$203 nightly
$225 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
"Exactly what you expect. Very nice good location"
Reviewed on Sep 25, 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.
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.
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.
Things to do
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
$74
per adult
100% of travellers recommend
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
Explore a world of travel with Expedia
- South Portland Hotels
- Scarborough Hotels
- B&B in Portland
- Cape Elizabeth Hotels
- Old Port Hotels
- Ogunquit Hotels
- Hotels near Portland Intl. Jetport
- Oceanfront Hotels in Old Orchard Beach
- Downtown Portland Hotels
- Hotels with Free Airport Shuttle in Portland
- Motels in Portland
- Old Orchard Beach Hotels
- Kennebunkport Hotels
- Oceanfront Hotels in Portland
- Freeport Hotels
- Wells Hotels
- Pet-Friendly Hotels in Portland
- Cheap Hotels in Portland
- Portland Hotels
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from Pittsburgh (PIT) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Hartford (BDL) to Portland (PWM)
- Flights from Chicago (ORD) to Portland (PWM)
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from Columbus (CMH) to Portland (PWM)
- Flights from San Francisco (SFO) to Portland (PWM)
- Flights from New York (NYC) to Portland (PWM)
- Flights from Phoenix (PHX) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Houston (IAH) to Portland (PWM)
- Flights to Portland
- Flights from Philadelphia (PHL) to Portland (PWM)
- Flights from Jacksonville (JAX) to Portland (PWM)
- Flights from St. Louis (STL) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights from Nashville (BNA) to Portland (PWM)
- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)
- Flights from Tucson (TUS) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Orlando (MCO) to Portland (PWM)
- Flights from Indianapolis (IND) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Cincinnati (CVG) to Portland (PWM)
- Flights from Richmond (RIC) to Portland (PWM)
- Flights from Miami (MIA) to Portland (PWM)
- Flights from Fort Lauderdale (FLL) to Portland (PWM)
- Flights from Cleveland (CLE) to Portland (PWM)
- Flights from Charlotte (CLT) to Portland (PWM)
- Flights from Austin (AUS) to Portland (PWM)
- Flights from Seattle (SEA) to Portland (PWM)
- Flights from Denver (DEN) to Portland (PWM)
- Flights from Baltimore (BWI) to Portland (PWM)
- Flights from Portland (PDX) to Portland (PWM)
- Flights from Washington (IAD) to Portland (PWM)
- Flights from Tampa (TPA) to Portland (PWM)
- Flights from White Plains (HPN) to Portland (PWM)
- Flights from Minneapolis (MSP) to Portland (PWM)
- Flights from Salt Lake City (SLC) to Portland (PWM)
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- 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.