Charlestown Vacation Packages
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Top Holiday Package Deals in Charlestown
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Boston
Bay Village
CA $2,769
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Fully refundableReserve now, pay when you stay
CA $345
CA $460 total
Oct 25 - Oct 26
includes taxes & fees
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $332
CA $435 total
Oct 25 - Oct 26
includes taxes & 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
Fully refundableReserve now, pay when you stay
CA $331
CA $385 total
Oct 25 - Oct 26
includes taxes & 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.
Frequently asked questions
How much does a Charlestown vacation package cost?
Starting from as low as CA $1,428, a package is your ticket to inexpensive travel. Customize your Charlestown trip by selecting from our wide range of hotels, flights and rental cars.
How do I get a cheap travel package to Charlestown?
Book everything in one place with our Charlestown vacation packages. We have deals on hotels, flights and more that'll keep your bank account happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options around the globe to choose from, there are endless opportunities to mix and match.
Where should I stay in Charlestown?
A journey to Charlestown has to include Fenway Park and TD Garden. Stay somewhere close by and easily access these fantastic sights.
What are the top hotels in Charlestown?
Moroccan Boutique Guest House and Top Of The World Charlestown Boston Ma are a couple of the most sought-after properties in Charlestown. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my Charlestown vacation?
Get rewarded with the widest variety at the lowest prices by booking your Charlestown vacation early. Air carriers usually sell flights around a year prior to departure, so start locking things in as soon as you can. That being said, Expedia is dedicated to providing you with the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Charlestown travel package include?
With Expedia, you can select a combination of flights, car rentals and hotels to create your perfect Charlestown travel package. Once you've made your booking, you can add on the fun things like tours and experiences. Remember, the more you bundle, the more cash you'll save!
What should I know before booking a Charlestown travel package?
When you book your hotels, flights and car rentals together, you'll enjoy terrific discounts. Whether you're organizing a beach escape in a villa or want to stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with a Charlestown Expedia vacation package?
Yes, you're in charge. Expedia has access to more than 550 airlines around the world, so you can design your Charlestown getaway according to your travel needs.
If I'm not able to travel, can I cancel my Charlestown vacation package?
Because we understand life can be unpredictable, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've booked your Charlestown vacation package in the last 24 hours, you may be able to change or cancel it without penalty. Your hotel, airline or car rental company may charge a fee if your booking is older than that.
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 Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.