Downtown Portland Vacations from $291
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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.
84 Main
Save 100% on your flight
Price was $428, price is now $291 per person
$291
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
10/10 Exceptional! (52 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!
Reviewed on Oct 26, 2025
The McKernan Inn
Save 100% on your flight
Price was $607, price is now $411 per person
$411
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!
Reviewed on Dec 27, 2025
Cliff House Maine
Bald Head
Save 100% on your flight
Price was $1,337, price is now $959 per person
$959
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Loved the hotel had a great time with a group of friends
Reviewed on Jan 12, 2026
Portland Harbor Hotel
Downtown Portland
Price was $974, price is now $708 per person
$708
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Reduce noise from patrons near elevator and coffee area on second floor, very loud
Reviewed on Jan 10, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $749, price is now $573 per person
$573
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is $108 total per night from Feb 8 to Feb 9
$108 total
per night
Feb 8 - Feb 9
8.8/10 Excellent! (1,002 reviews)
What a great stay and great breakfast
Reviewed on Jan 18, 2026
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
The price is $86 total per night from Jan 29 to Jan 30
$86 total
per night
Jan 29 - Jan 30
8.8/10 Excellent! (1,469 reviews)
Room was very clean, bed was comfortable. Would stay here again.
Reviewed on Jan 20, 2026
Canopy by Hilton Portland Waterfront
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
The price is $118 total per night from Feb 2 to Feb 3
$118 total
per night
Feb 2 - Feb 3
9.4/10 Exceptional! (1,000 reviews)
Room was spotless and staff was very corteus!
Reviewed on Jan 10, 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
Explore a world of travel with Expedia
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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.