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

Downtown Portland Vacations from $527

Book a Hotel + Flight or Car together to unlock savings

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.
  • A well-lit living room with a fireplace, comfortable seating, and a large mirror.
    Feb 2 - Feb 5

    Blind Tiger Portland – Carleton Street + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (137 reviews)
    "Quick responses by staff! Comfortable bed! Gorgeous amenities! Loved the location was right down from Tandem Coffee!"
    Reviewed October 21, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $674
    $527
    per traveler
    found 1 day ago
    Blind Tiger Portland – Carleton Street
  • A spacious kitchen with a central island, wooden bar stools, and a long dining table.
    Jan 7 - Jan 12

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    5 nights
    3.5 star property
    9.6/10 - Exceptional (206 reviews)
    Roundtrip • Dallas (DFW) - Portland (PWM)
    DAL - PWM • 1 stop PWM - DFW • 1 stop
    $1,467
    $1,153
    per traveler
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.
    Feb 2 - Feb 5

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (431 reviews)
    "The property was excellent. We stayed in a 1 bedroom loft and it was great. Nice sitting area, fully equipped kitchen, beautiful bathroom and nice size bedroom. It was quiet and comfy, and also walking distance to great restaurants. Highly recommend."
    Reviewed November 12, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - PWM • 1 stop PWM - MCO • Nonstop
    $815
    $654
    per traveler
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • A backyard with a fire pit, wooden chairs, and a house with a porch.
    Jan 7 - Jan 12

    Inn By The Sea + Flight

    Cape Elizabeth
    5 nights
    4.0 star property
    9.6/10 - Exceptional (347 reviews)
    Roundtrip • Dallas (DFW) - Portland (PWM)
    DAL - PWM • 1 stop PWM - DFW • 1 stop
    $1,292
    $1,084
    per traveler
    found 1 day ago
    Inn By The Sea
  • An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.
    Dec 30 - Jan 5

    Canopy by Hilton Portland Waterfront + Flight

    Downtown Portland
    6 nights
    4.0 star property
    9.4/10 - Exceptional (1,005 reviews)
    Roundtrip • New York (NYC) - Portland (PWM)
    EWR - PWM • Nonstop PWM - EWR • Nonstop
    $1,307
    $1,103
    per traveler
    found 21 hours ago
    Canopy by Hilton Portland Waterfront

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
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.

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.

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.

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.

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.

Discover the most popular places to visit in Downtown Portland

A multi-story brick building with a large arched window and a sign that reads "STATE".

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.
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What to do near Downtown Portland

Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour

Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour

$32
per adult
0% of travelers recommend
Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour
See all activities near Downtown Portland

Downtown Portland Hotel Deals

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
4.0 star property
Downtown Portland
9.0 out of 10, Wonderful, (1,683 reviews)
"Everything was super clean and we got a room with the view of the bay. As always Holiday Inn does not disappoint. We weren’t able to get the breakfast in the morning due to our flight but everything else was great."
$87 nightly
The price is $97
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.