Charlestown Vacation Packages

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Top Holiday Package Deals in Charlestown

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,347, price is now CA $1,478 per person
CA $1,478
per person
Jun 21 - Jun 24
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Staff was great room was cute!

Reviewed on Apr 10, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,594, price is now CA $1,655 per person
CA $1,655
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $2,722, price is now CA $1,794 per person
CA $1,794
per person
May 15 - May 21
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,002 reviews)
The room was very spacious and clean. The staff was excellent especially the chefs in the boardwalk 400. One of the lamps didn't work in my room but it was quickly replaced. The refrigerator was unplugged. Otherwise, my stay was enjoyable!

Reviewed on Apr 5, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $4,045, price is now CA $2,719 per person
CA $2,719
per person
Jun 21 - Jun 24
found 16 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (248 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Nantucket Town
Price was CA $5,279, price is now CA $3,661 per person
CA $3,661
per person
Jun 30 - Jul 6
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.

Reviewed on Sep 26, 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

Downtown Boston

4.5/5(197 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
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Apr 12 to Apr 13
CA $275
CA $321 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
Breakfast was amazing! Service of the people was pretty friendly and very professional

Reviewed on Apr 10, 2026

Residence Inn by Marriott Boston Harbor on Tudor Wharf
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from May 10 to May 11
CA $281
CA $384 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,579 reviews)
Impressive

Reviewed on Apr 10, 2026

Omni Boston Hotel at the Seaport
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 $209 per night from May 10 to May 11
CA $209
CA $291 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,160 reviews)
Very well kept hotel with terrific food options in and around the hotel. The staff is very friendly and helpful.

Reviewed on Apr 10, 2026

Seaport Hotel Boston
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.
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Frequently asked questions

How much does a Charlestown vacation package cost?
Starting from as low as CA $1,478, 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

USS Constitution is a three masted wooden hulled heavy frigate of the United States Navy docked at Charlestown Navy Yard in Boston, Massachusetts MA, USA. She is the world's oldest ship still afloat.

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
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
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

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
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 $115
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $108
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.