Downtown Portland Vacations from $678
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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 $1,218, price is now $797 per person
$797
per person
May 1 - May 7
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (56 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Inn By The Sea
Save 100% on your flight
Price was $1,470, price is now $1,103 per person
$1,103
per person
May 1 - May 7
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (302 reviews)
Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away
Reviewed on Mar 4, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $1,222, price is now $931 per person
$931
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was $1,132, price is now $879 per person
$879
per person
May 23 - May 26
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!
Reviewed on Feb 23, 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
$98 nightly
The price is $108 total per night from Apr 5 to Apr 6
$108 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Just a great place to stay
Reviewed on Mar 10, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $137 total per night from Mar 23 to Mar 24
$137 total
Mar 23 - Mar 24
Total with taxes and fees
9.4/10 Exceptional! (1,600 reviews)
The hotel beds are comfy! And the steam room (locker room) is a fave. But my room was loud! From street noise and the transparent sound passing between the walls throughout the night. I thought this would be my easeful winter getaway spot but I think I’ll keep searching….
Reviewed on Mar 15, 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 Mar 22 to Mar 23
$86 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (1,480 reviews)
The overnight front desk worker was rude. Paying to park was not advertised on Expedia.
Reviewed on Mar 13, 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
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
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
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
Ultimate Portland Self-Guided Driving GPS Audio Tour
$17
per traveler
100% of travellers recommend
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
$69
per adult
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.