Charlestown Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Charlestown

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Price was CA $904, price is now CA $617 per person
CA $617
per person
Aug 25 - Aug 28
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
9.2/10 Wonderful! (1,170 reviews)
Great place to stay, very clean, and the staff was very friendly.

Reviewed on Jul 13, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,988, price is now CA $1,829 per person
CA $1,829
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Love coming back to a refreshed clean room after a long hot day of sightseeing.

Reviewed on Jul 15, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $2,078, price is now CA $1,385 per person
CA $1,385
per person
Sep 10 - Sep 14
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) 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

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,397, price is now CA $939 per person
CA $939
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The staff here was so kind and thoughtful. The breakfast was amazing all 3 days and the beach was very quiet and great waterfront. The section we stayed has not been updated like some of the other units but was fine and comfortable. The general location was good and easily walkable to food and drink places. Overall, we enjoyed it and would stay here again for sure.

Reviewed on Jul 12, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,418, price is now CA $1,671 per person
CA $1,671
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything was great. Definitely will recommend

Reviewed on Jul 12, 2026

Where to stay in Charlestown

Find the best Charlestown areas and neighborhoods for the activities you enjoy most. Learn more about Charlestown
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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.

Find hotels in Downtown Boston

Charlestown Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Jul 26 to Jul 27
CA $280
CA $374 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,590 reviews)
"Great location."

Reviewed on Jul 15, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Aug 2 to Aug 3
CA $225
CA $262 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,751 reviews)
"Great location; great rooms; felt safe for solo traveling. Rooms cleans and spacious. Bathrooms kept cleaned. The only experience I had was getting locked out of room and staff came up to help and didn’t even ask me if I needed assistance. I had to walk to lobby in my night gown."

Reviewed on Jul 15, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $268 per night from Aug 9 to Aug 10
CA $268
CA $353 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,431 reviews)
"good view of the river and city"

Reviewed on Jul 15, 2026

Hyatt Regency Boston/Cambridge
See all 4,160 properties in Charlestown
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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Charlestown vacation package cost?
Starting from as low as CA $617, 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

The USS Constitution Museum building with multiple colorful banners and flags.

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.”
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $68
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.