
Chestnut Hill Vacations from $343
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Your Chestnut Hill Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to Boston College, Paradise Rock Club and Agganis Arena, some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Chestnut Hill today.
The Latest Chestnut Hill Vacation Packages


Ocean Air Suites
Reviewed on Sep 3, 2024


The Cove At Salem
Reviewed on Jul 11, 2025
Where to stay in Chestnut Hill

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.
Chestnut Hill Hotel Deals

Reviewed on Jul 11, 2025

Reviewed on Jul 10, 2025

Reviewed on Jul 10, 2025
Discover the most popular places to visit in Chestnut Hill

Boston College
Take a campus tour or just explore the area of Boston College, during your trip to Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.
Alumni Stadium
Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.
McMullen Museum
You can study the exhibits at McMullen Museum, a museum with a storied past, during your travels to Newton. Experience the fascinating museums or attend a sporting event in this vibrant area.
Things to do

Boston CityPASS®: Admission to Top 4 Attractions

Liberty, Freedom, and Revolution: American History Tours Bundle
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- Alumni Stadium
- Boston College
- Cleveland Circle Vacations
- Andover Newton Theological School
- Larz Anderson Auto Museum
- Boston Museum of Fine Arts
- Boston Vacations
- Frederick Law Olmsted National Historic Site
- The Silver Woman
- Visit Cleveland Circle
- Arnold Arboretum
- St. Elizabeth's Medical Center
- Visit Newton Center
- Brookline Vacations
- Isabella Stewart Gardner Museum
- Jamaica Plain Vacations
- Brookline Farmers Market
- Coolidge Corner Theatre
- Newton Vacations
- Visit Newton Highlands
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