Downtown Portland Vacations from $401
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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.
The Meadowmere Resort
Price was $564, price is now $476 per person
$476
per person
Dec 28 - Dec 30
found 17 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)
The people who worked at Meadowmere were very nice! I thought it needed a little updating. The TV wasn’t easy to find our way around. The pool wasn’t heated so I didn’t go in. We were supposed to have a continental breakfast included but we went down at 9 am this morning before leaving and the doors were locked. Yesterday it was open early. The location was good, close to the shops but we probably won’t stay again.
Reviewed on Nov 2, 2026
Portland Harbor Hotel
Downtown Portland
Price was $603, price is now $509 per person
$509
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,851 reviews)
Nice design, exceptional staff and a convenient location in the Old Port neighborhood. Fitness room includes Pelotons.
Reviewed on Nov 2, 2026
The Kendall Inn
Price was $572, price is now $484 per person
$484
per person
Dec 2 - Dec 5
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.8/10 Exceptional! (166 reviews)
We truly enjoyed our stay at the Kendall Inn. The staff were very welcoming and their cooking was excellent. They even accommodated my gluten allergy at meals. Would highly recommend staying here!
Reviewed on Oct 31, 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
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
$108 nightly
The price is $119 total per night from Nov 22 to Nov 23
$119 total
Nov 22 - Nov 23
Total with taxes and fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $196 total per night from Nov 29 to Nov 30
$196 total
Nov 29 - Nov 30
Total with taxes and fees
9.2/10 Wonderful! (1,857 reviews)
"Nice design, exceptional staff and a convenient location in the Old Port neighborhood. Fitness room includes Pelotons."
Reviewed on Nov 2, 2026
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
$91 nightly
The price is $101 total per night from Dec 1 to Dec 2
$101 total
Dec 1 - Dec 2
Total with taxes and fees
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.
Stay near popular Downtown Portland attractions
Things to do
Harbor Lights and Sights Cruise
$61
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
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- Victoria Mansion
- Bug Light
- Old Port Vacations
- Portland Museum of Art
- Casco Bay Bridge
- Ll Bean Flagship Store
- Mclellan-Sweat Mansion
- Charles Q. Clapp House
- Fitzpatrick Stadium
- Higgins Beach
- Two Lights State Park
- Eastern Promenade
- International Cryptozoology Museum
- Casco Bay Lines Ferry Terminal
- Port City Music Hall
- Merrill Auditorium
- Wadsworth-Longfellow House
- Maine Sports Hall of Fame
- State Street Church
- Visit Bailey Island
- State Theatre
- Fort Preble
- Portland Head Light
- Spring Point Ledge Lighthouse
- Maine College of Art
- Fort Williams Park
- East End Beach
- Visit Portland
- Southworth Planetarium
- Maine Jewish Museum
- Maine Historical Society
- Mclellan-Sweat House
- Visit Old Port
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.