Charlestown Vacations from $733
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Your Charlestown Vacation
Our Charlestown vacation packages are a simple and practical way to organize and reserve your next adventure. Uncover the true character of this unique neighborhood without the fuss of having to organize everything yourself. Hoping to head out and see the sights during your trip to Charlestown? Be sure to stop by nearby attractions such as Fenway Park, Boston Common and Faneuil Hall Marketplace. Expedia can put your plans into action. Book your ideal Charlestown vacation today.
The Latest Charlestown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
$1,290
per person
Dec 5 - Dec 12
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Four Seasons Hotel Boston
Bay Village
$1,250
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (484 reviews)
Room was very noisy in the morning and I could not sleep. Work is being done in the building and I was not informed of when arriving from west coast to stay for one night. Staff was very friendly and apologetic.
Reviewed on Sep 25, 2026
Where to stay in Charlestown
Find the best Charlestown areas and neighborhoods for the activities you enjoy most. Learn more about Charlestown
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.
Back Bay
1 out of top 10 points of interest in this area
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.
Seaport District
1 out of top 10 points of interest in this area
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.
Beacon Hill
1 out of top 10 points of interest in this area
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.
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.
Charlestown Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
$279 nightly
$325 total
Oct 25 - Oct 26
Total with taxes and fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
$265 nightly
$307 total
Oct 25 - Oct 26
Total with taxes and fees
9.6/10 Exceptional! (5,034 reviews)
"The hotel was clean and the fresh flowers in the lobby were beautiful. The bartender in the bar made a delicious espresso martini. Our room was clean, but the bathroom fan did not work and the tub had a huge piece scraped off. Also, the light in the coffee station was burned out. Overall, we enjoyed ..."
Reviewed on Sep 25, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
$269 nightly
$313 total
Sep 27 - Sep 28
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.
Stay near popular Charlestown attractions
Bunker Hill Monument
8.8/10 (90 reviews)
Enjoy breathtaking views of Boston and delve into the region’s revolutionary history at this iconic granite monument.
USS Constitution Museum
9.0/10 (1,904 reviews)
Play sailor and learn even more about the U.S. Navy’s oldest ship at a museum just across from “Old Ironsides.”
Charlestown Navy Yard
10.0/10 (1 review)
You can find out about the history of Boston with a visit to Charlestown Navy Yard. Experience the fascinating museums or attend a sporting event in this vibrant area.
Zakim Bunker Hill Bridge
One of the world’s widest cable-stayed bridges graces Boston’s skyline with a functional monument to the city’s long commitment to democracy and freedom.
Boston National Historical Park
Explore the great outdoors at Boston National Historical Park, a lovely green space in Boston. Amble around this vibrant area's waterfront or experience its fascinating museums.
Engine Company 50
Learn about the local history of Boston when you spend time at Engine Company 50. Experience the fascinating museums or attend a sporting event in this vibrant area.
Charlestown Navy Yard Visitor Center
You can browse the exhibits at Charlestown Navy Yard Visitor Center, a museum with a storied past, during your travels to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
Winthrop Park
Explore the great outdoors at Winthrop Park, a lovely green space in Boston. Discover the fascinating museums in this vibrant area, or seek out the local tours.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$37
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
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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.