Charlestown Vacation Packages

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Top Holiday Package Deals in Charlestown

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 19 - Aug. 22
found 9 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
What a treat it was stay at this hotel. Besides the fact it is absolutely stunning with great attention to detail, the staff was also fantastic, from the valet, to the doormen to front desk and cleaning service. Special shout out to Thomas from front desk who we dealt with for our stay. Made sure to have a room ready for us for early check in and always made sure we had everything we needed. We had a 10 month old, they had a crib ready for us which was a life saver. Location was also fantastic. All in all a 10/10 across the board and we cannot wait to stay there again.

Reviewed on Jun. 12, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug. 2 - Aug. 6
found 7 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
This was a wonderful overnight stop in Boston. We will be back.

Reviewed on Jun. 17, 2024

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (4 reviews)
Everything was perfect

Reviewed on May 28, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Aug. 21 - Aug. 28
found 23 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9/10 Wonderful! (155 reviews)
I loved the small, boutique size of the hotel. The staff were amazing, especially Austin Griffith. He was a huge help with making all my plans and his recommendations were spot on.

Reviewed on Jun. 14, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 26 - Aug. 29
found 12 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on Jun. 9, 2024

Where to stay in Charlestown

Find the best Charlestown areas and neighborhoods for the activities you enjoy most. Learn more about Charlestown
Downtown Boston which includes night scenes and a city 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 hotel + flight trips in Downtown Boston

Charlestown Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $283 per night from Jul. 3 to Jul. 4
CA $283
CA $377 total
includes taxes & fees
Jul 3 - Jul 4
9/10 Wonderful! (2,066 reviews)
"Loved this hotel! Staff were awesome! So many staff. Also used spa and ate at the Sporting Club (which was also great except for the runner who slammed our food down in the wrong places without a care). Looking forward to trying more Omni hotels in the future."

Reviewed on Jun. 16, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul. 4 to Jul. 5
CA $251
CA $340 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,706 reviews)
Boston!
"This historic hotel was a perfect place to stay in Boston!"

Reviewed on Jun. 17, 2024

Omni Parker House
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
The price is CA $232 per night from Jun. 30 to Jul. 1
CA $232
CA $270 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (1,568 reviews)
A great hotel experience at a fair price.
"I enjoyed my stay at the Revolution Hotel very much. It's located in a nice part of Boston where you can easily access public transportation or walk."

Reviewed on Jun. 17, 2024

The Revolution Hotel
See all 3,190 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.

Explore other types of vacation packages

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 $1,402, 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

Image for USS Constitution Museum

USS Constitution Museum

Play sailor and learn even more about the U.S. Navy’s oldest ship at a museum just across from “Old Ironsides.”

USS Constitution Museum
Image for Bunker Hill Monument

Bunker Hill Monument

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

Bunker Hill Monument
Image for 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

Things to do

Image for Boston Freedom Trail Self-Guided Walking Tour

Boston Freedom Trail Self-Guided Walking Tour

CA $12
Per adult
82% of travellers recommend
Boston Freedom Trail Self-Guided Walking Tour
Image for Entire Freedom Trail Walking Tour: Includes Bunker Hill and USS Constitution

Entire Freedom Trail Walking Tour: Includes Bunker Hill and USS Constitution

CA $107
Per adult
100% of travellers recommend
Entire Freedom Trail Walking Tour: Includes Bunker Hill and USS Constitution
Image for Bunker Hill Monument Self-Guided Walking Tour

Bunker Hill Monument Self-Guided Walking Tour

CA $11
Per adult
Bunker Hill Monument Self-Guided Walking Tour
See all activities in Boston

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.