Downtown Portland Vacations from $449
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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
Price was $598, price is now $449 per person
$449
per person
Feb 12 - Feb 16
found 1 day 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
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $891, price is now $546 per person
$546
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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
The Docent’s Collection – Thompson Block
Downtown Portland
Save 100% on your flight
Price was $1,162, price is now $801 per person
$801
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.
Reviewed on Jan 10, 2026
The McKernan Inn
Price was $908, price is now $627 per person
$627
per person
Apr 2 - Apr 7
found 1 day 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
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 Feb 8 to Feb 9
$108 total
Feb 8 - Feb 9
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
$138 nightly
The price is $152 total per night from Jan 25 to Jan 26
$152 total
Jan 25 - Jan 26
Total with taxes and fees
9.4/10 Exceptional! (1,573 reviews)
Room is awesome , love the hotel.
Reviewed on Jan 12, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $150 total per night from Feb 10 to Feb 11
$150 total
Feb 10 - Feb 11
Total with taxes and fees
9.2/10 Wonderful! (1,754 reviews)
The room was wonderful. All the staff were kind and welcoming. They kindly helped us solve a problem that came up. We hope to be back again next year. Beautiful hotel.
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
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
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.