Downtown Portland Vacations from $491
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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 $756, price is now $491 per person
$491
per person
Mar 18 - Mar 22
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
I had a Junior Suite and it was lovely. Bed was extremely comfortable and it was very quiet. I will say the breakfast is costly in my opinion but it was great.
Reviewed on Jan 6, 2026
The McKernan Inn
Price was $793, price is now $543 per person
$543
per person
Mar 18 - Mar 22
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $861, price is now $635 per person
$635
per person
Mar 18 - Mar 22
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.
Reviewed on Dec 24, 2025
Cliff House Maine
Bald Head
Save 100% on your flight
Price was $1,458, price is now $1,082 per person
$1,082
per person
Apr 3 - Apr 6
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!!
The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!
Reviewed on Jan 6, 2026
84 Main
Price was $694, price is now $522 per person
$522
per person
Feb 12 - Feb 16
found 17 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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
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 Jan 25 to Jan 26
$108 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.
Reviewed on Jan 6, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $142 total per night from Jan 11 to Jan 12
$142 total
Jan 11 - Jan 12
Total with taxes and fees
9.4/10 Exceptional! (1,567 reviews)
Staff was great. Perfect location to explore the area.
Reviewed on Jan 4, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $143 total per night from Jan 11 to Jan 12
$143 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (1,746 reviews)
One of the reasons we have returned to this hotel for the third time was the set up on each floor with cookies, coffee, etc. However, each time we went to the area there were no cookies or snacks of any kind - not even bottles of water or ice. I texted the front desk and they said that due to the ...
Reviewed on Jan 5, 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.
Maine College of Art
You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's entertainment choices and great live music.
Things to do
Portland Smartphone Audio Tour: Self-Guided Drive
$15
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.