Plan a trip to see N.W. Barrett Gallery

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Ramada Plaza by Wyndham Portland

Nasons Corner

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

7.8/10 Good! (1,032 reviews)

Great option to explore Portland.

Reviewed on Aug. 3, 2025

Portland Harbor Hotel

Downtown Portland

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.2/10 Wonderful! (1,542 reviews)

Moderate luxury in the heart of everything Portland. Lots of shopping and dining in a short walk. The amenities fee is unusual.

Reviewed on Aug. 2, 2025

Cliff House Maine

per person

Oct 16 - Oct 19

found 3 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,008 reviews)

The Cliff House is a one of a kind! Always a fantastic visit!

Reviewed on Aug. 1, 2025

Tours & day trips

See all 62 activities

Portland: Best of Maine Lighthouse Scenic Cruise

Free cancellation available

Food, drink & nightlife

See all 13 activities

Portland: Casco Bay Sunset and Lighthouse Cruise

Free cancellation available

Private & custom tours

See all 9 activities

City centre Golden Adventure Quest Experience in Portland

Free cancellation available

Adventure & outdoor

See all 5 activities

Around The Peninsula Bike Tour

Free cancellation available

Holiday & seasonal tours

See all 3 activities

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Free cancellation available

Popular places to visit

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 waterfront or experience its entertainment choices.

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.

Wadsworth-Longfellow House

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.

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 acclaimed theater scene and great live music.

Fore Street Gallery

You can spend an afternoon studying the exhibits at Fore Street Gallery during your trip to Portland. Experience the area's great live music and entertainment choices.

Maine Sports Hall of Fame

You can spend an afternoon studying the exhibits at Maine Sports Hall of Fame during your travels in Portland. Stroll along the area's seaside or experience its acclaimed theater scene.