A river winding through a city with industrial buildings and a bridge.

South Side Vacations from $430

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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

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

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Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most.

Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Quincy Market with its neoclassical architecture, including columns and a prominent sign.

A historic building with a clock tower, surrounded by modern skyscrapers.

A cityscape with historic buildings, including a prominent clock tower and a modern skyscraper.

Quincy Market with a prominent clock tower, American flag, and a street vendor area.

View properties in map for Downtown Boston

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.

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A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

A historic building with intricate architecture, a modern skyscraper, and a fountain in a park.

A historic building with intricate architecture, large arched windows, and statues in front.

A historic red brick building with ornate detailing and a clock tower, located at a busy intersection with modern buildings and traffic.

A city skyline with sailboats on a calm body of water.

View properties in map for Back Bay

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

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A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

A large, illuminated ship docked at a pier with fireworks in the background.

A city skyline at night with illuminated buildings reflecting on the water.

A city skyline at dusk with illuminated buildings and a calm river.

View properties in map for Seaport District

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

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A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

A large building with a golden dome, red brick walls, and white columns.

A large building with a golden dome, red brick columns, and a staircase leading to the entrance.

A cityscape with a prominent golden dome building, surrounded by lush greenery and a river in the background.

A narrow alley with cobblestone path, brick buildings, and climbing ivy.

View properties in map for Beacon Hill

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

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A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

A historic street with red brick buildings, a prominent church steeple, and a clear blue sky.

A metal plaque with the inscription "BOSTON TRAIL" and a decorative emblem.

A brick building with a sign for the Paul Revere House Museum.

A cityscape with a river, historic buildings, and a prominent tower.

View properties in map for North End

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

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South Side Hotel Deals

HYATT house Boston/Waltham

An outdoor patio area with a fire pit, seating, and a grill.
  • Address: 54 4th Ave, Waltham, MA, 02451, US
  • Location: 2.3 mi from South Side
  • Star rating: 3/5
  • Guest rating: 9/10 (Wonderful, 1200 reviews)
  • Price: $107 nightly, $120 total, Nov 20 - Nov 21, Total with taxes and fees
  • Review: The hotel was clean, rooms were spacious, the staff were excellent. The breakfast was delicious

The Westin Waltham-Boston

A modern restaurant with large windows, leather seating, and a bar area.
  • Address: 70 Third Avenue, Waltham, MA, 02451, US
  • Location: 2.4 mi from South Side
  • Star rating: 4/5
  • Guest rating: 8.8/10 (Excellent, 1155 reviews)
  • Price: $101 nightly, $113 total, Dec 4 - Dec 5, Total with taxes and fees
  • Review: Very comfy, cozy and clean! Front Staff were great.

Best Western Plus Waltham Boston

A restaurant setting with round tables, chairs, and empty wine glasses.
  • Location: Piety Corner, 2.5 mi from South Side
  • Guest rating: 8.4/10 (Very good, 1358 reviews)
  • Price: $70 nightly, $78 total, Dec 6 - Dec 7, Total with taxes and fees
  • Review: Excellent experience

Hampton Inn & Suites Boston/Waltham

A modern kitchen with a central island, bar stools, and a dining area with a large table.
  • Address: 135 2nd Ave, Waltham, MA, 02451, US
  • Location: 2.4 mi from South Side
  • Star rating: 3/5
  • Guest rating: 9.4/10 (Exceptional, 2052 reviews)
  • Price: $94 nightly, $105 total, Dec 6 - Dec 7, Total with taxes and fees

Fairfield Inn & Suites by Marriott Boston Waltham

A modern living room with a fireplace, sofas, a dining area, and a TV mounted above the fireplace.
  • Address: 250 Second Avenue, Waltham, MA, 02451, US
  • Location: 2.1 mi from South Side
  • Star rating: 3/5
  • Guest rating: 9/10 (Wonderful, 1001 reviews)
  • Price: $112 nightly, $125 total, Nov 15 - Nov 16, Total with taxes and fees
  • Review: Such an amazing hotel! Everything is just like the photos. Will definitely stay here again

Hilton Garden Inn Boston/Waltham

A modern café with a chilled beverage fridge, a frozen section, and a variety of snacks and drinks.
  • Address: 450 Totten Pond Rd, Waltham, MA, 02451, US
  • Location: 2.4 mi from South Side
  • Star rating: 3.5/5
  • Guest rating: 9/10 (Wonderful, 1001 reviews)
  • Price: $77 nightly, $85 total, Nov 28 - Nov 29, Total with taxes and fees
  • Review: Would stay again

Courtyard by Marriott Boston Waltham

A courtyard with a fire pit, outdoor seating, and a brick building in the background.
  • Address: 387 Winter St, Waltham, MA, 02451, US
  • Location: Piety Corner, 2.6 mi from South Side
  • Star rating: 3/5
  • Guest rating: 9.2/10 (Wonderful, 1007 reviews)
  • Price: $105 nightly, $117 total, Nov 15 - Nov 16, Total with taxes and fees

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.