Downtown Portland Vacations from $932
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Your Downtown Portland Vacation
Book your vacation package to Downtown Portland and get ready to enjoy its markets and more. Whether you're searching for adventure or relaxation, you'll find it in this appealing neighborhood. Some popular nearby attractions to check out during your trip to Downtown Portland include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Expedia is here to help put your travel plans into action. Book your perfect Downtown Portland vacation today.
The Latest Downtown Portland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
Downtown Portland
$1,039
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (65 reviews)
Amazing rooms amazing staff perfect location absolutely amazing !!!! Can’t wait to
Go back
Reviewed on Sep 27, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$973
per person
Dec 3 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (395 reviews)
We have stayed in this Docents Collections building in the recent past and this room did not live up to our expectations. I thought I had booked a two-bedroom with two bathrooms. Perhaps because I inadvertently got onto Expedia's site and also due to booking fairly last minute, we ended up with a corner room with one bath not attached to either of the two bedrooms, and windows that faced a close by brick wall and parking garage. We encourage Docents Collection to invest in a few more amenities for this unit, including waste bins in the bedrooms and more than one pillow and throw in the sitting area.
The location is great and the staff is friendly and accommodating.
Reviewed on Sep 27, 2026
Cliff House Maine
Bald Head
$1,171
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
It is a perfect place to stay
I can’t think of anything I did not like can’t wait to visit again
Reviewed on Sep 27, 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 Neal S. Dow House and Fitzpatrick Stadium.
Downtown Portland Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$277 nightly
$306 total
Oct 25 - Oct 26
Total with taxes and fees
9.2/10 Wonderful! (1,865 reviews)
"We absolutely loved this hotel. The location was perfect for our ladies trip. The staff were beyond helpful!!! And the rooms were very well maintained. thank you very much….."
Reviewed on Sep 28, 2026
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
$147 nightly
$163 total
Oct 29 - Oct 30
Total with taxes and fees
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$192 nightly
$212 total
Oct 25 - Oct 26
Total with taxes and fees
9.2/10 Wonderful! (1,338 reviews)
"Staff and room were amazing! Only downside was the tv, which doesn’t allow you to hook up a fire stick or connect to your phone. Other than that, a very enjoyable stay!"
Reviewed on Sep 28, 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 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.
Photo by Tim Thomas
Maine College of Art
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's acclaimed theater scene and great live music.
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 waterfront or experience its entertainment choices.
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.
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 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
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- Victoria Mansion
- Bug Light
- Old Port Vacations
- Portland Museum of Art
- Casco Bay Bridge
- Ll Bean Flagship Store
- Mclellan-Sweat Mansion
- Charles Q. Clapp House
- Fitzpatrick Stadium
- Higgins Beach
- Two Lights State Park
- Eastern Promenade
- International Cryptozoology Museum
- Casco Bay Lines Ferry Terminal
- Port City Music Hall
- Merrill Auditorium
- Wadsworth-Longfellow House
- Maine Sports Hall of Fame
- State Street Church
- Visit Bailey Island
- State Theatre
- Fort Preble
- Portland Head Light
- Spring Point Ledge Lighthouse
- Maine College of Art
- Fort Williams Park
- East End Beach
- Visit Portland
- Southworth Planetarium
- Maine Jewish Museum
- Maine Historical Society
- Mclellan-Sweat House
- Visit Old Port
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.