Downtown Portland Vacations from $577
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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.
Nautical Mile
$577
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
The Meadowmere Resort
$658
per person
Nov 19 - Nov 23
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Great mid-price range option! Still walking distance to most things you’ll want to do in ogunquit and they let you check in early just to park even if your room isn’t ready yet, which is valuable in of itself. The outdoor horrible was very spacious and the up keep of the entire property was very nice. Free continental breakfast too
Reviewed on Oct 11, 2026
84 Main
$716
per person
Nov 20 - Nov 24
found 8 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (58 reviews)
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
Snowvillage Inn
$893
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.8/10 Excellent! (304 reviews)
The location was off the beaten path and in the woods. Quiet cozy room ( no TV ) price was more than reasonable considering what hotels on the Conway strip cost. Free breakfast was simple, apples,oranges, muffins, pastries, coffee, tea. Stayed for Fryburg Fair.20 minutes away. Hot water in the morning was an issue as it was only lukewarm both shower and sink . Wall heater in bathroom didn’t work but wasn’t needed ( 35 degrees outside). Electric heat worked . These issues I’ve had in major Hotels . Rooms at Marriott, Hilton, no name motels were 2+ times higher in price the same time we stayed for the Fair. The hot water did work when we first arrived as my wife took her shower but not in the morning..
Reviewed on Oct 12, 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.
West End
Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
West Bayside
If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.
East Bayside
Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.
Downtown Portland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$127 nightly
$141 total
Nov 11 - Nov 12
Total with taxes and fees
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$209 nightly
$231 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Fully refundable
$102 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,661 reviews)
"The room was beautiful, clean and comfortable. The most comfortable hotel beds we have slept in this trip. Front desk staff was extremely helpful and kind. Loved that they have a shuttle to take you to the hotspots so you don’t have to move your car and pay for parking."
Reviewed on Oct 14, 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.
Stay near popular Downtown Portland attractions
State Theatre
8.8/10 (392 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
9.2/10 (610 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
Photo by Tim Thomas
Maine College of Art
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's acclaimed theater scene and great live music.
Wadsworth-Longfellow House
8.6/10 (119 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.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
Merrill Auditorium
8.8/10 (107 reviews)
You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Fore Street Gallery
You can spend an afternoon studying the exhibits at Fore Street Gallery during your trip to Portland. Experience the area's entertainment choices and great live music.
Monument Square
8.0/10 (1 review)
Find out about the history of Portland when you spend time at Monument Square. Stroll along the area's waterfront or experience its acclaimed theater scene.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% 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.