
South Side Vacations from $206
Book a Hotel + Flight or Car together to unlock savings
Your South Side Vacation
Take all the hassle out of organizing your next getaway with a South Side vacation package. Take in the sights and sounds of this unique neighborhood and experience all it has to offer. Start your trip to South Side by heading to nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District. Expedia is here to put your travel plans into action. Book your perfect South Side vacation now.
The Latest South Side Vacation Packages

Club Quarters Hotel Faneuil Hall, Boston
Reviewed on Nov 25, 2025

Boston Lodge and Suites
Reviewed on Nov 10, 2025

Iris Hotel Boston
Reviewed on Nov 22, 2025

The Wylie Inn and Conference Center at Endicott College
Reviewed on Nov 26, 2025

Marriott Boston Quincy
Reviewed on Nov 23, 2025
Where to stay in South Side

Downtown Boston
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
South Side Hotel Deals

citizenM Boston North Station
Rooms were clean, staff was friendly
Reviewed on Nov 25, 2025

Omni Boston Hotel at the Seaport
Room ready when we arrived at 8:30am Small but suffices Noise from outside is easily heard
Reviewed on Nov 25, 2025

The Revolution Hotel
The room a stay itself were wonderful. A 20 minute walk or quick train ride to any sight we wanted to see. Parking was limited to only the local garage, which had a discounted rate of $35/day through the hotel. Otherwise, the streets in the area were permit parking only.
Reviewed on Nov 24, 2025
Discover the most popular places to visit in South Side

Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Boston Common
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Things to do

Boston CityPASS®: Admission to Top 4 Attractions

























