Downtown Portland Vacations
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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.
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- Admiral Peary Inn
Aug 3 - Aug 6Admiral Peary Inn + Flight
Fryeburg3 nights9.0/10 - Wonderful (49 reviews)"DNA "Reviewed March 22, 2026Roundtrip • Chicago (ORD) - Boston (BOS)ORD - BOS • Nonstop BOS - ORD • Nonstop$564$414found 1 day agoper traveler - The Meadowmere Resort
Jul 20 - Jul 27The Meadowmere Resort + Flight
Ogunquit7 nights8.6/10 - Excellent (1,001 reviews)"The room was recently renovated and was immaculate. The beds and pillows were very good, as was the shower pressure. The chairs were uncomfortable. There needs to be handicapped parking available near the rooms. I would not recommend the Pub. The service was excellent, but the food was subpar."Reviewed May 30, 2026Roundtrip • Chicago (ORD) - Portland (PWM)ORD - PWM • Nonstop PWM - ORD • Nonstop - Ogunquit River Inn & Suites
Aug 20 - Aug 24Ogunquit River Inn & Suites + Flight
Ogunquit4 nights9.0/10 - Wonderful (1,005 reviews)"Super nice staff"Reviewed June 1, 2026Roundtrip • Chicago (ORD) - Portland (PWM)ORD - PWM • Nonstop PWM - ORD • Nonstop - Cliff House Maine
Jul 7 - Jul 9Cliff House Maine + Flight
Bald Head2 nights9.4/10 - Exceptional (1,002 reviews)"Staff was very helpful. Polite and friendly."Reviewed May 20, 2026Roundtrip • New York (JFK) - Portland (PWM)JFK - PWM • Nonstop PWM - JFK • Nonstop - Newagen Seaside Inn
Aug 2 - Aug 6Newagen Seaside Inn + Flight
Southport4 nights9.4/10 - Exceptional (344 reviews)"Beautiful hotel, amazing grounds with water views, a nice pool, gazebo, outdoor games for kids and adults and an indoor gameroom too. Mike and i enjoyed the ping pong table. Definitely worth the money and we will be back to stay again. The restaurant at the hotel had gormet food and wonderful, friendly service. The server also went out of his way to check if the hotel would be lighting the firepit outside because we mentioned we would like to have a quiet night by the fire. The hotel staff..."Reviewed May 30, 2026Roundtrip • New York (EWR) - Bangor (BGR)EWR - BGR • Nonstop BGR - EWR • Nonstop
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(484 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
$313 nightly
The price is $346 total per night from Jun 7 to Jun 8
$346 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (1,760 reviews)
"The staff, room service and breakfast all great. I will stay again at this property with a exception location."
Reviewed on Jun 1, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$287 nightly
The price is $318 total per night from Jun 15 to Jun 16
$318 total
Jun 15 - Jun 16
Total with taxes and fees
9.4/10 Exceptional! (1,224 reviews)
"Convenient and dog friendly."
Reviewed on May 31, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $267 total per night from Jun 7 to Jun 8
$267 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (1,668 reviews)
"Always a wonderful stay at the Regency!"
Reviewed on May 31, 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(258 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(79 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.
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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.