Charlestown Vacation Packages

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Top Holiday Package Deals in Charlestown

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was CA $750, price is now CA $529 per person
CA $529
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.8/10 Good! (790 reviews)
The Area was quiet,

Reviewed on Aug. 31, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,136, price is now CA $1,168 per person
CA $1,168
per person
Nov 5 - Nov 7
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
We had a wonderful stay at the Boston Harbor Hotel - the staff was friendly and our room excellent! Thank you!

Reviewed on Aug. 31, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Price was CA $1,996, price is now CA $1,390 per person
CA $1,390
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
7.4/10 Good! (89 reviews)
Had a 4 night stay at the Maverick Suites on Temple Street. I mainly booked this room to be close to my daughter, who lives a couple of doors down. The room is a bit tight for two people, but my friend & I made it work by sleeping 90 degrees on the double bed to turn it into more of a "short king". Room was very clean, however the one suggestion I would make is to use less of the strong-smelling cleaner (Fabioso?) or a more natural cleaner. Otherwise, the property felt safe and clean. Beautiful hardwood floors, nice bathroom & small kitchen area. Staff is very responsive via TEXT (not by phone). We requested clean towels etc, and they were very accommodating. Temple St. is walkable to many sites you'll want to check out in Boston via a walk or to the Park St T station. I would recommend staying at the Maverick Suites!

Reviewed on Jun. 25, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $2,248, price is now CA $1,570 per person
CA $1,570
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8/10 Very Good! (588 reviews)
Good location. Think the following items should have been in the unit: Tea towel, dish cloth, paper towels, sink stopper and 4 coffees (for 4 individuals). Both shower stalls should include shelves for shampoo, soap etc. FYI, the glass stove top has brown stains. The concierges were very friendly and helpful.

Reviewed on Aug. 31, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $1,132, price is now CA $806 per person
CA $806
per person
Oct 10 - Oct 13
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (30 reviews)
Very impressed! Very clean, friendly staff, felt safe, the room was far bigger than expected, I’ll be back!

Reviewed on Sep. 1, 2025

Where to stay in Charlestown

Find the best Charlestown areas and neighborhoods for the activities you enjoy most. Learn more about Charlestown
Downtown Boston showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(193 area reviews)

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

Residence Inn by Marriott Boston Harbor on Tudor Wharf

Residence Inn by Marriott Boston Harbor on Tudor Wharf

3 out of 5
34-44 Charles River Ave, Boston, MA
The price is CA $333 per night from Sep 21 to Sep 22
CA $333
CA $387 total
Sep 21 - Sep 22
includes taxes & fees
Residence Inn by Marriott Boston Harbor on Tudor Wharf
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 $321 per night from Sep 4 to Sep 5
CA $321
CA $381 total
Sep 4 - Sep 5
includes taxes & fees
Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $378 per night from Sep 21 to Sep 22
CA $378
CA $496 total
Sep 21 - Sep 22
includes taxes & fees
Omni Boston Hotel at the Seaport
See all 3,726 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Charlestown vacation package cost?
Starting from as low as CA $529, 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.

Discover the most popular places to visit in Charlestown

Bunker Hill Monument

Bunker Hill Monument

4.5/5(8 reviews)

Enjoy breathtaking views of Boston and delve into the region’s revolutionary history at this iconic granite monument.

Bunker Hill Monument
Charlestown Navy Yard

Charlestown Navy Yard

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.

Charlestown Navy Yard
Zakim Bunker Hill Bridge

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.

Zakim Bunker Hill Bridge

Things to do

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace

CA $14
per traveller
84% of travellers recommend
Explore Boston’s Freedom Trail: Self-Guided Audio Tour at Your Own Pace
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
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.