Old Port Vacations from $491
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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.
Portland Harbor Hotel
Downtown Portland
Price was $756, price is now $491 per person
$491
per person
Mar 18 - Mar 22
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
I had a Junior Suite and it was lovely. Bed was extremely comfortable and it was very quiet. I will say the breakfast is costly in my opinion but it was great.
Reviewed on Jan 6, 2026
The McKernan Inn
Price was $793, price is now $543 per person
$543
per person
Mar 18 - Mar 22
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!
Reviewed on Dec 27, 2025
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $861, price is now $635 per person
$635
per person
Mar 18 - Mar 22
found 20 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.
Reviewed on Dec 24, 2025
Cliff House Maine
Bald Head
Save 100% on your flight
Price was $1,458, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 6
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!!
The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!
Reviewed on Jan 6, 2026
84 Main
Price was $694, price is now $522 per person
$522
per person
Feb 12 - Feb 16
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
10/10 Exceptional! (52 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!
Reviewed on Oct 26, 2025
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
4.5/5(326 area reviews)
Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.
Old Port Hotel Deals
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $142 total per night from Jan 11 to Jan 12
$142 total
Jan 11 - Jan 12
Total with taxes and fees
9.4/10 Exceptional! (1,567 reviews)
Staff was great. Perfect location to explore the area.
Reviewed on Jan 4, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $143 total per night from Jan 11 to Jan 12
$143 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (1,746 reviews)
One of the reasons we have returned to this hotel for the third time was the set up on each floor with cookies, coffee, etc. However, each time we went to the area there were no cookies or snacks of any kind - not even bottles of water or ice. I texted the front desk and they said that due to the ...
Reviewed on Jan 5, 2026
Canopy by Hilton Portland Waterfront
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $123 total per night from Feb 2 to Feb 3
$123 total
Feb 2 - Feb 3
Total with taxes and fees
9.4/10 Exceptional! (1,014 reviews)
Awesome stay
Reviewed on Jan 2, 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.
Discover the most popular places to visit in Old Port
Cross Insurance Arena
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Casco Bay Lines Ferry Terminal
Explore the waterfront in Portland with a trip to Casco Bay Lines Ferry Terminal. Discover the top-notch restaurants and great live music in this family-friendly area.
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 waterfront or experience its great live music.
Things to do
Portland Smartphone Audio Tour: Self-Guided Drive
$15
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
$10
per traveler
Ultimate Portland Self-Guided Driving GPS Audio Tour
$17
per traveler
100% of travellers recommend
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- Portland Vacations
- N.W. Barrett Gallery
- Downtown Portland Vacations
- Casco Bay Lines Ferry Terminal
- Maine Sports Hall of Fame
- Cross Insurance Arena
- Merrill Auditorium
- Wadsworth-Longfellow House
- Victoria Mansion
- Maine Historical Society
- Museum of African Culture
- Center for Maine History
- Maine College of Art
- Space Gallery
- Maine Jewish Museum
- Portland Museum of Art
- Charles Q. Clapp House
- Visit Portland
- McLellan-Sweat Mansion
- McLellan-Sweat House
- State Theatre
- Visit Downtown Portland
- Portland Fire Museum
- Maine Narrow Gauge Railroad Company and Museum
- Cathedral Church of Saint Luke
- International Cryptozoology Museum
- State Street Church
- Center for Cultural Exchange
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- Car rental Portland Airport (PWM)
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- Van Car Rentals in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.