Downtown Portland Vacations from $529
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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 Meadowmere Resort
$647
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room, paid breakfast, front office staff very efficient, very limited items even in paid breakfast section.check in time 4 pm and check out 11 am.
Reviewed on Sep 2, 2026
The Wolfeboro Inn
$757
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
8.2/10 Very Good! (631 reviews)
Just returned from a several-day stay at the Wolfeboro Inn. It was absolutely delightful! Clearly an older establishment, but well-maintained and very clean, cozy, and comfortable. The staff was especially friendly and helpful. Very welcoming! Sweet location right on the lake & close to the lovely downtown - so pretty! Extra kudos also to the tavern…the food is excellent at great prices!
👏🤗👏
Reviewed on Sep 1, 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.
Parkside
While visiting Parkside, you might make a stop by sights like Fitzpatrick Stadium and Neal S. Dow House.
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.
Downtown Portland Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$367 nightly
$406 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (1,826 reviews)
"Our room was very hot and we were unable to sleep. The temperature was 78 degrees all night, despite trying to adjust the thermostat. I complained in the morning but was given no apology or adjustment to the bill. We paid nearly $800 to sweat all night and not sleep."
Reviewed on Sep 4, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$195 nightly
$216 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"I think it comes down to the mark-up is beyond acceptable. You be the judge: 3 nights king bed room with no view, parking and breakfast for 2 = $1,700."
Reviewed on Sep 1, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$284 nightly
$314 total
Sep 7 - Sep 8
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 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 great live music and acclaimed theater scene.
State Street Church
Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.
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 acclaimed theater scene.
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.
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 acclaimed theater scene.
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
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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.