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Boston vacations

NOTE: Flight service for Boston vacations is into Boston, MA, Manchester, NH or Providence, RI.

One of the United States’ oldest cities, Boston has a rich and storied history. The city is dotted with historic and exciting attractions that are sure to keep you busy during your vacation. Walk through the Boston Common, one of the country’s oldest city parks, and catch a glimpse of more than a dozen significant American Revolutionary sites along the Freedom Trail. When you get hungry, you’ll delight in Boston’s eclectic dining options. Don’t forget to catch a big league game at Fenway Park or get an up close look at exotic marine life at the New England Aquarium. Create your ideal Boston vacation package with Southwest Vacations today.

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Featured Boston hotels

These are just a few of our available hotels in Boston, we have many more available! Perform a search to see all the options Southwest Vacations® has to offer.

Featured things to do

Here are just a handful of activities available. We have tons more! You can add these and many others to your vacation package during the booking process.

Boston, MA


Explore a piece of American history, plus save up to $120 roundtrip per person because Bags Fly Free® with Southwest Vacations. See the Boston Commons, tour the USS Constitution, take in a game at Fenway Park, and visit the home of Paul Revere. Boston also offers numerous world-class museums, art galleries, and family-orientated attractions. Book your Boston vacation package today.

Boston resorts and hotels

Discover the wide range of accommodations available with a Boston vacation package. Select from three, four, and five-star Boston resorts and hotels. Find accommodations throughout the Greater Boston area including the Bay Area, City Center, Copley Square, Downtown Boston, and more. Conveniently add one of these great resorts or hotels to your Boston vacation package from Southwest Vacations.

Boston activities, attractions, and tours

History and culture in Boston: Visit places in American history with a Boston Culture Vacation Package. Walk along the Freedom Trail, tour the U.S.S. Constitution, see the Bunker Hill Monument, witness the Boston Tea Party Ship & Museum, explore the Boston National Historical Park, Paul Revere House & Museum, and the John F. Kennedy National Historic Site. Other museums in Boston include the Museum of Fine Arts Boston, the John Fitzgerald Kennedy Library & Museum, the Cahoon Museum of American Art, and the Museum of Afro-American History. Book a historical Boston vacation package from Southwest Vacations today.

Sports in Boston: Cheer for your favorite sports teams with a Boston Sports Vacation Package. From September through December, watch the New England Patriots play football at Gillette Stadium. During October through April, witness both the Boston Bruins play hockey and the Boston Celtics play basketball at the TD Banknorth Garden. March through September sees the Boston Red Sox play baseball at historic Fenway Park. Join the excitement with a Boston vacation package from Southwest Vacations.

Discover the benefits of booking with Southwest Vacations.


First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

Learn about Southwest Vacations' travel protection. Be protected from the unexpected. Learn about bags fly free.  Applies to your first and second checked bags. Weight and size limits apply. Sign up for exclusive offers, get deals and special offers delivered directly to your inbox.