Plan a trip to see Monument Square

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The Docent's Collection

Downtown Portland

per person

Sep 13 - Sep 16

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

9.6/10 Exceptional! (211 reviews)

Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.

Reviewed on Jul. 31, 2025

Cliff House Maine

per person

Sep 4 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

9.4/10 Exceptional! (1,008 reviews)

Beautiful property with great service and dining options. Rooms were spacious with nautical decor. Pool was beautiful but get there early if you want a lounge with umbrella!

Reviewed on Jul. 30, 2025

Portland Harbor Hotel

Downtown Portland

per person

Sep 13 - Sep 16

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

9.2/10 Wonderful! (1,523 reviews)

We really enjoyed our stay. Great location, staff couldn’t have been more friendly, and a clean comfortable room. Snacks and a Keurig in the hall for all on the floor to share was nice, although there was something wrong with the Keurig. (It worked, but there were multiple times I had to run it twice.)

Reviewed on Jul. 31, 2025

Tours & day trips

See all 62 activities

Portland: Best of Maine Lighthouse Scenic Cruise

Free cancellation available

Food, drink & nightlife

See all 14 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

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.

Charles Q. Clapp House

Demonstrating the wealth and artistic sensibilities of 19th-century Portland, this masterpiece of Greek Revival architecture is next to the Portland Museum of Art.

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

McLellan-Sweat Mansion

Providing a window into Maine’s prosperous past, this well-preserved early 19th-century brick mansion and house museum forms the back of the Portland Museum of Art.

Maine Historical Society

You can spend time browsing the exhibits at Maine Historical Society in Portland. Stroll along the area's waterfront or experience its entertainment choices.