Downtown Portland Vacations from $438
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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.
Portland Harbor Hotel
Downtown Portland
Price was $579, price is now $438 per person
$438
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Room and service were good. Resort fee of $35 a day and parking was $45 a day
Reviewed on Feb 16, 2026
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $691, price is now $488 per person
$488
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from
Reviewed on Jan 23, 2026
The Weldon Hotel
Downtown Portland
Price was $648, price is now $486 per person
$486
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.
Reviewed on Jan 3, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was $724, price is now $555 per person
$555
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy!
Well curated style and knowledgeable staff.
Reviewed on Jan 5, 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
4.5/5(473 area reviews)
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.
Downtown Portland Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $164 total per night from Feb 18 to Feb 19
$164 total
Feb 18 - Feb 19
Total with taxes and fees
9.2/10 Wonderful! (1,760 reviews)
Nice decor and amenities (pantry)
Reviewed on Feb 11, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $132 total per night from Mar 1 to Mar 2
$132 total
Mar 1 - Mar 2
Total with taxes and fees
9.4/10 Exceptional! (1,585 reviews)
Loved the sauna / spa! Will definitely make this a regular getaway destination.
Reviewed on Feb 9, 2026
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
$78 nightly
The price is $86 total per night from Feb 22 to Feb 23
$86 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (1,482 reviews)
Lovely room, great breakfast
Reviewed on Feb 15, 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 Downtown Portland
State Theatre
4.5/5(88 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
4.5/5(255 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Wadsworth-Longfellow House
4/5(78 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.
Things to do
Portland Smartphone Audio Tour: Self-Guided Drive
$17
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
- Visit Old Port
- Old Port Vacations
- Cross Insurance Arena
- N.W. Barrett Gallery
- Casco Bay Lines Ferry Terminal
- Victoria Mansion
- Wadsworth-Longfellow House
- Museum of African Culture
- Maine Historical Society
- Center for Maine History
- Maine Sports Hall of Fame
- Maine College of Art
- Merrill Auditorium
- Space Gallery
- Portland Museum of Art
- Charles Q. Clapp House
- McLellan-Sweat Mansion
- McLellan-Sweat House
- State Theatre
- Maine Jewish Museum
- Portland Fire Museum
- Visit Portland
- Cathedral Church of Saint Luke
- International Cryptozoology Museum
- State Street Church
- Center for Cultural Exchange
- Maine Narrow Gauge Railroad Company and Museum
- Visit Portland Arts District
- Casco Bay Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.