Waterfront Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Holiday Package Deals in Waterfront

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn

Lakeside Inn

2 out of 5
Price was CA $918, price is now CA $586 per person
CA $586
per person
Oct 28 - Nov 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,174 reviews)
nice stay, liked the room and bed, breakfast could have been better,

Reviewed on Aug. 23, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,932, price is now CA $1,605 per person
CA $1,605
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,852, price is now CA $1,722 per person
CA $1,722
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,801, price is now CA $1,233 per person
CA $1,233
per person
Oct 28 - Nov 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Price was CA $1,091, price is now CA $748 per person
CA $748
per person
Oct 28 - Nov 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (693 reviews)
The staff was very courteous and professional! The room was clean and comfortable.

Reviewed on Aug. 23, 2025

Where to stay in Waterfront

Find the best Waterfront areas and neighborhoods for the activities you enjoy most. Learn more about Waterfront
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

Waterfront Hotel Deals

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
70 Rowes Wharf, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $728 per night from Sep 1 to Sep 2
CA $728
CA $848 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,010 reviews)
"Great location. Beautiful building and setting. Staff are helpful and friendly!"

Reviewed on Aug. 24, 2025

Boston Harbor Hotel
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 $249 per night from Sep 1 to Sep 2
CA $249
CA $347 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,840 reviews)
"Overall a great hotel. Well located, the seaport zone is really beautiful. Public transportation access"

Reviewed on Aug. 21, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Sep 1 to Sep 2
CA $268
CA $312 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,692 reviews)
"Decor and furnishings unique. Refreshing and different. View from lounge area of Boston skyline is amazing!"

Reviewed on Aug. 24, 2025

citizenM Boston North Station
See all 3,726 properties in Waterfront
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 Waterfront vacation package cost?
The cheapest Waterfront package is CA $586, so your dream trip can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to custom build a package that fits you.
How do I get a cheap travel package to Waterfront?
Find flights that fit your schedule, add a hotel room to your booking and see how much you save with a Waterfront vacation package. It's that easy! From flights and hotels to activities and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 airlines and 1,000,000 properties around the world to select from, you'll never be short of choice.
Where should I stay in Waterfront?
Urban adventurers come from near and far to see Fenway Park and TD Garden in Waterfront. Book a room close to these popular attractions and visit them whenever you please.
What are the top hotels in Waterfront?
If it's your very first time in Waterfront, book a room at Boston Marriott Long Wharf or Boston Harbor Hotel. Both will make you feel at home and are favorites with many travelers.
How far in advance should I book my Waterfront vacation?
Savvy travelers often reserve their seats as early as possible. You can normally compare international fares on Expedia up to 12 months before your intended flight. If you're late to book, fear not. Budget prices sometimes appear just weeks before departure.
What does an Expedia Waterfront travel package include?
Select from a combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like activities and tours. Want to pick your airfare class? That's also easy to do. The choice is yours when it comes to arranging your dream Waterfront escape.
What should I know before booking a Waterfront travel package?
You'll pick up impressive savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything in one place will make your trip planning easier. So why waste time or money? Whether you're organizing a luxury romantic escape or a budget family adventure, browse our package deals today.
Can I choose my airline with a Waterfront Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Just choose the airline you want and put together your ideal Waterfront vacation.
If I'm not able to travel, can I cancel my Waterfront vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you've booked your Waterfront vacation package in the last 24 hours, you may be able to change or cancel it free of charge. 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 Waterfront

New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium
Boston Harbor

Boston Harbor

Adore Boston’s charming working harbor from the waterfront or head out by boat to get to know it more intimately.

Boston Harbor
Long Wharf

Long Wharf

Explore the waterfront in Boston with a trip to Long Wharf. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Long Wharf

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

CA $41
per traveller
Liberty, Freedom, and Revolution: American History Tours 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.