Plan a trip to see Umbrella Cover Museum

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The Weldon Hotel

Downtown Portland

CA $1,251

per person

Oct 27 - Oct 30

found 21 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Portland (PWM)

9.8/10 Exceptional! (71 reviews)

This is probably the cleanest, most beautiful hotel for the money we’ve ever stayed in. The nightly rate was comparable to the other hotel rooms in town, but here you get a huge spacious apartment! All new, chic, and very comfortable. Easy to walk to Wharf St. and the dining and shopping area too! The manager was very responsive, friendly and accommodating as well! This place is a gem!

Reviewed on Aug. 26, 2025

The Docent's Collection

Downtown Portland

CA $1,826

per person

Oct 9 - Oct 12

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

9.6/10 Exceptional! (226 reviews)

Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.

Reviewed on Aug. 25, 2025

Hampton Inn Portland Downtown - Waterfront

Downtown Portland

CA $1,572

per person

Oct 9 - Oct 12

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

8.8/10 Excellent! (1,004 reviews)

The staff was remarkable, friendly, ready to help with any need.

Reviewed on Aug. 27, 2025

Tours & day trips

See all 63 activities

Portland: Best of Maine Lighthouse Scenic Cruise

Free cancellation available

Food, drink & nightlife

See all 15 activities

Portland: Casco Bay Sunset and Lighthouse Cruise

Free cancellation available

Private & custom tours

See all 10 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

Classes & workshops

See all 3 activities

Portland: Schooner Tall Ship Cruise on Casco Bay

Free cancellation available

Popular places to visit

Fort Preble

On the South Portland waterfront, survey the scene of the Battle of Portland Harbor, which is the only known Civil War conflict fought in Maine.

Southern Maine Community College

Walk around the campus at Southern Maine Community College as part of your travels around South Portland. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Bug Light

You can find out about the history of South Portland with a visit to Bug Light. Experience the area's entertainment choices and great live music.

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.

Richard Boyd Art Gallery

You can spend time studying the exhibits at Richard Boyd Art Gallery during your trip to Peaks Island. Stroll along the area's waterfront or experience its great live music.

Fifth Maine Museum

You can spend time studying the exhibits at Fifth Maine Museum during your travels in Peaks Island. Experience the area's entertainment choices and great live music.