Plan a trip to see South Portland Historical Society Museum

Price found within the past 48 hours. Click for updated prices.

The Newbury Boston

Back Bay

CA $956

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (490 reviews)

Love the Street Bar!

Reviewed on Aug. 25, 2025

Raffles Boston

Back Bay

CA $2,160

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (154 reviews)

I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug. 28, 2025

Studio Allston Hotel

Brighton

CA $1,539

per person

Oct 13 - Oct 18

found 14 hours ago

Roundtrip flight included

Vancouver (YVR) to Boston (BOS)

8.6/10 Excellent! (1,098 reviews)

Great spot. Friendly helpful staff.

Reviewed on Aug. 25, 2025

Tours & day trips

See all 61 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 10 activities

City centre Golden Adventure Quest Experience in Portland

Free cancellation available

Adventure & outdoor

See all 4 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

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.

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.

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.

Portland Observatory

You can find out about the history of Portland with a visit to Portland Observatory. Stroll along the area's waterfront or experience its acclaimed theater scene.

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.