Downtown Portland Vacations from $687
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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 Weldon Hotel
Downtown Portland
$1,025
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (112 reviews)
The room was very clean and nice. The only thing that was not so great was the loud motor going on and off for some of the night. Otherwise it was great!
Reviewed on Aug 26, 2026
Inn By The Sea
$1,803
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 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.
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.
Parkside
While visiting Parkside, you might make a stop by sights like Fitzpatrick Stadium and Neal S. Dow House.
Downtown Portland Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$244 nightly
$270 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Room was excellent. Location is good but if you have mobility issues then you would have to Uber to waterfront/shops. Valet/complimentary shuttle unreliable."
Reviewed on Aug 29, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$314 nightly
$348 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,814 reviews)
"For the price I would expect more amenities. The “free” food by the elevator was pretty sparse with a broken ice machine and coffee maker"
Reviewed on Aug 29, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$193 nightly
$213 total
Aug 30 - Aug 31
Total with taxes and fees
9.4/10 Exceptional! (1,723 reviews)
"Unless they are booked solid. I ONLY stay at the regency over the last several years. Fourth floor roof deck suite market street side ftw! Cheers!"
Reviewed on Aug 28, 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 great live music and acclaimed theater scene.
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.
State Street Church
Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.
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 acclaimed theater scene.
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 acclaimed theater scene.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland Explorer: Boat Cruise with Oysters & Prosecco
$137
per adult
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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.