East Bayside Vacations from $764

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Your East Bayside Vacation

Booking an East Bayside vacation package is an ideal way to become acquainted with this unique neighborhood. From its must-visit places to its little-known secrets, there's plenty to discover. Some leading nearby attractions to see during your trip to East Bayside include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Stop dreaming and start doing. When you're ready to book your ideal vacation to East Bayside, Expedia is here to help.

The Latest East Bayside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
$764
per person
Nov 19 - Nov 22
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (70 reviews)
This place is gorgeous! I highly recommend it. Beautiful modern design with everything you might need. Great central location. A bit hard to find. Parking was A lot! But made life easier. Will stay here again.

Reviewed on Oct 6, 2026

Cliff House Maine

Cliff House Maine

Bald Head
Save 100% on your flight
$1,166
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
$765
per person
Dec 15 - Dec 22
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
$1,195
per person
Dec 27 - Dec 30
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

Inn By The Sea

Inn By The Sea

$814
per person
Nov 19 - Nov 22
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)

Where to stay in East Bayside

Find the best East Bayside areas and neighborhoods for the activities you enjoy most. Learn more about East Bayside
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area

Known for its culinary delights, inspiring art and live music, the heart of Maine’s largest city is an exciting location.

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A marina with boats docked, a wooden pier, and a red brick building with balconies.

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.

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A lighthouse on a rocky shore with a sailboat in the distance.

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.

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A large, cream-colored building with white columns and a white picket fence in front.

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.

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An aerial view of a coastal city with a harbor, marina, and residential area.

Parkside

While visiting Parkside, you might make a stop by sights like Neal S. Dow House and Fitzpatrick Stadium.

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Stay near popular East Bayside attractions

Maine Jewish Museum

Located in the immigrant-era Etz Chaim Synagogue, this museum tells the stories of Maine’s Jewish families and showcases Jewish artists from the area.
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Cathedral of the Immaculate Conception

Find out about the history of Portland with a stop at Cathedral of the Immaculate Conception. Stroll along the area's seaside or experience its entertainment choices.
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Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.