A statue of a historical figure with a pedestal, a large stone monument in the background, and a park with a bench and trees.

Charlestown Vacations from $533

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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.
  • A glass-fronted fireplace with visible logs and flames, set on a wooden floor.
    Dec 10 - Dec 12

    Boston Lodge and Suites + Flight

    Dorchester
    2 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Dallas (DFW) - Boston (BOS)
    DFW - BOS • Nonstop BOS - DFW • 1 stop
    $890
    $533
    per traveler
    found 1 day ago
    Boston Lodge and Suites
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 21 - Jan 24

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,007 reviews)
    "All the staff was very helpful and responsive I would recommend this hotel to everyone planning to stay in Boston."
    Reviewed November 9, 2026
    Roundtrip • Burbank (BUR) - Boston (BOS)
    BUR - BOS • 1 stop BOS - BUR • 1 stop
    $1,557
    $973
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • A large, classical building with multiple windows and a prominent entrance.
    Jan 21 - Jan 24

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,005 reviews)
    Roundtrip • Burbank (BUR) - Boston (BOS)
    BUR - BOS • 1 stop BOS - BUR • 1 stop
    $1,118
    $823
    per traveler
    found 1 day ago
    The Langham, Boston
  • A brick building with arched windows and a black door, surrounded by greenery and a metal fence.
    Jan 14 - Jan 18

    Four Seasons Hotel Boston + Flight

    Bay Village
    4 nights
    5.0 star property
    9.4/10 - Exceptional (497 reviews)
    "The best location and the beat service! The best swimming pool"
    Reviewed November 9, 2026
    Roundtrip • Los Angeles (LAX) - Boston (BOS)
    LAX - BOS • Nonstop BOS - LAX • Nonstop
    $2,092
    $1,550
    per traveler
    found 1 day ago
    Four Seasons Hotel Boston
  • Pool
    Jan 21 - Jan 24

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (355 reviews)
    "Great place to stay!!"
    Reviewed November 9, 2026
    Roundtrip • Burbank (BUR) - Boston (BOS)
    BUR - BOS • 1 stop BOS - BUR • 1 stop
    $1,622
    $1,218
    per traveler
    found 14 hours ago
    Raffles Boston

Where to stay in Charlestown

Find the best Charlestown areas and neighborhoods for the activities you enjoy most. Learn more about Charlestown
Learn more about Charlestown
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

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.

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

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.

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

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.

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

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.

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

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.

Discover the most popular places to visit in Charlestown

A street lined with historic buildings and a prominent Washington Monument in the center.

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.
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What to do near Charlestown

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travelers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities near Charlestown

Charlestown Hotel Deals

A waterfront hotel with a dock and marina, featuring multiple floors and a prominent building with a sign.

Residence Inn by Marriott Boston Harbor on Tudor Wharf

Residence Inn by Marriott Boston Harbor on Tudor Wharf
3.0 star property
Charlestown
9.2 out of 10, Wonderful, (1,008 reviews)
"Staff is very friendly and accommodating. I stay atleast 1 time a year and I can tell they have been doing upgrades around the hotel"
$139 nightly
The price is $162
Nov 22 - Nov 23
Total with taxes and fees
Residence Inn by Marriott Boston Harbor on Tudor Wharf
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.
See all properties in Charlestown
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.