
Highlands Vacations from $464
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Your Highlands Vacation
Organizing your next exciting getaway just got simpler with a vacation package to Highlands. Immerse yourself in the very best this neighborhood has to offer while making nice memories you won't forget. Not sure what to do and see during your trip to Highlands? Nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District are great places to start. Don't just think about it — make it a reality! Book your ideal Highlands vacation with Expedia and travel your way.
The Latest Highlands Vacation Packages



John Carver Inn & Spa
Reviewed on Jul 17, 2025

The Cove At Salem
Reviewed on Jul 18, 2025

Ocean Air Suites
Reviewed on Jul 17, 2025
Where to stay in Highlands

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.
Discover the most popular places to visit in Highlands

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

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

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.
Things to do

Boston CityPASS®: Admission to Top 4 Attractions
