Plan a trip to see Portland Observatory

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Hampton Inn Portland Downtown - Waterfront

Downtown Portland

per person

Oct 10 - Oct 13

found 9 hours ago

Roundtrip flight included

Windsor (YQG) to Portland (PWM)

8.8/10 Excellent! (1,005 reviews)

Staff were very nice and very accommodating. We paid for the convenience of this hotel’s location. It is pretty tired and the rooms & bathrooms are showing some significant wear and tear. Hampton Inn bedding is not very nice. It’s enough to make me want to switch from Hilton to Marriott (Hampton vs courtyard - courtyard’s bedding wins every time.)

Reviewed on Aug. 7, 2025

The Docent's Collection

Downtown Portland

per person

Oct 10 - Oct 13

found 9 hours ago

Roundtrip flight included

Windsor (YQG) to Portland (PWM)

9.6/10 Exceptional! (219 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

Blind Tiger Portland – Carleton Street

West End

per person

Oct 10 - Oct 13

found 9 hours ago

Roundtrip flight included

Windsor (YQG) to Portland (PWM)

9.8/10 Exceptional! (114 reviews)

The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on Jul. 23, 2025

Tours & day trips

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Portland: Best of Maine Lighthouse Scenic Cruise

Free cancellation available

Food, drink & nightlife

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Portland: Casco Bay Sunset and Lighthouse Cruise

Free cancellation available

Private & custom tours

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City centre Golden Adventure Quest Experience in Portland

Free cancellation available

Adventure & outdoor

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Around The Peninsula Bike Tour

Free cancellation available

Holiday & seasonal tours

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Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Free cancellation available

Popular places to visit

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.

East Prom Trail

Former rail beds are often turned into trails. At this one you can walk, run, bike or swim for active relaxation within the city.

Eastern Promenade

Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.

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.

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

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.