A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland Vacations from $514

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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.

Dec 29 - Jan 3
Dormir + Flight
Windham
5 nights
3.0 star property
9.0/10 - Wonderful (1,004 reviews)
"I love this place. This is the 2nd time I've stayed here. It's clean, quiet, well located. The staff is friendly and helpful. I would recommend it to anyone."
Reviewed November 3, 2026
Roundtrip • Philadelphia (PHL) - Portland (PWM)
PHL - BOS • Nonstop BOS - PHL • Nonstop
~~$644~~
$514
per traveler
found 1 day ago
Dormir
Dec 27 - Dec 31
Blind Tiger Portland - Danforth Street. + Flight
West End
4 nights
3.5 star property
9.6/10 - Exceptional (204 reviews)
Roundtrip • Minneapolis (MSP) - Portland (PWM)
MSP - PWM • 1 stop PWM - MSP • 1 stop
~~$1,738~~
$1,367
per traveler
found 5 hours ago
Blind Tiger Portland - Danforth Street.
Dec 29 - Jan 3
Waldo Emerson Inn + Flight
Kennebunk
5 nights
3.0 star property
9.4/10 - Exceptional (357 reviews)
"Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home. The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day. What truly made our experience special were the..."
Reviewed October 18, 2026
Roundtrip • Philadelphia (PHL) - Portland (PWM)
PHL - BOS • Nonstop BOS - PHL • Nonstop
~~$955~~
$764
per traveler
found 1 day ago
Waldo Emerson Inn
Dec 27 - Dec 31
The Docent's Collection at 121 Middle Street + Flight
Downtown Portland
4 nights
3.5 star property
9.6/10 - Exceptional (427 reviews)
Roundtrip • Minneapolis (MSP) - Portland (PWM)
MSP - PWM • 1 stop PWM - MSP • 1 stop
~~$1,350~~
$1,114
per traveler
found 5 hours ago
The Docent's Collection at 121 Middle Street
Dec 27 - Dec 31
Inn By The Sea + Flight
Cape Elizabeth
4 nights
4.0 star property
9.6/10 - Exceptional (345 reviews)
Roundtrip • Minneapolis (MSP) - Portland (PWM)
MSP - PWM • 1 stop PWM - MSP • 1 stop
~~$1,291~~
$1,072
per traveler
found 5 hours ago
Inn By The Sea

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

An aerial view of a coastal city with dense urban development, a marina, and a large body of water.

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.

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The Victoria Mansion Historic House Museum with a clear blue sky in the background.

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.

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A historic building with a sign reading "Portland Museum of Art McLellan House."

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.

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An aerial view of a coastal town with houses, a parking lot, and a rocky shoreline.

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.

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A sign for the Maine Jewish Museum with a brick building in the background.

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.

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