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.

Price found within the past 48 hours. Click for updated prices.
  • Aug 3 - Aug 6

    Admiral Peary Inn + Flight

    Fryeburg
    3 nights
    3.0 star property
    9.0/10 - Wonderful (49 reviews)
    "DNA "
    Reviewed March 22, 2026
    Roundtrip Chicago (ORD) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    $564
    $414
    per traveler
    found 1 day ago
    Admiral Peary Inn
  • Jul 20 - Jul 27

    The Meadowmere Resort + Flight

    Ogunquit
    7 nights
    2.5 star property
    8.6/10 - 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, 2026
    Roundtrip Chicago (ORD) - Portland (PWM)
    ORD - PWMNonstop PWM - ORDNonstop
    Save 100% on your flight
    $2,995
    $1,868
    per traveler
    found 1 day ago
    The Meadowmere Resort
  • Aug 20 - Aug 24

    Ogunquit River Inn & Suites + Flight

    Ogunquit
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,005 reviews)
    "Super nice staff"
    Reviewed June 1, 2026
    Roundtrip Chicago (ORD) - Portland (PWM)
    ORD - PWMNonstop PWM - ORDNonstop
    Save 100% on your flight
    $1,588
    $1,051
    per traveler
    found 1 day ago
    Ogunquit River Inn & Suites
  • Jul 7 - Jul 9

    Cliff House Maine + Flight

    Bald Head
    2 nights
    4.5 star property
    9.4/10 - Exceptional (1,002 reviews)
    "Staff was very helpful. Polite and friendly."
    Reviewed May 20, 2026
    Roundtrip New York (JFK) - Portland (PWM)
    JFK - PWMNonstop PWM - JFKNonstop
    Save 100% on your flight
    $1,300
    $952
    per traveler
    found 1 day ago
    Cliff House Maine
  • Aug 2 - Aug 6

    Newagen Seaside Inn + Flight

    Southport
    4 nights
    3.5 star property
    9.4/10 - 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, 2026
    Roundtrip New York (EWR) - Bangor (BGR)
    EWR - BGRNonstop BGR - EWRNonstop
    Save 100% on your flight
    $1,249
    $918
    per traveler
    found 1 day ago
    Newagen Seaside Inn

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

Downtown Portland Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
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

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
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

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
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

Portland Regency Hotel & Spa
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.