Downtown Crossing Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Downtown Crossing

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
per person
Sep 25 - Sep 28
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
It was a pleasant stay. The staffs were friendly. The room had both microwave and fridge. Although the room was neat, the cleaners did miss a couple of things.

Reviewed on Jun. 29, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
The Bed was extremely comfortable,The harbor view was beautiful

Reviewed on Jul. 12, 2025

Where to stay in Downtown Crossing

Find the best Downtown Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Crossing
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 hotels in Downtown Boston

Downtown Crossing Hotel Deals

The Godfrey Hotel Boston
The Godfrey Hotel Boston
4 out of 5
505 Washington Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 27 to Jul 28
CA $215
CA $314 total
Jul 27 - Jul 28
includes taxes & fees
9.4/10 Exceptional! (4,143 reviews)
"The only dining options within walking distance we found were "fast food" options."

Reviewed on Jul. 8, 2025

The Godfrey Hotel Boston
Hyatt Regency Boston
Hyatt Regency Boston
4 out of 5
One Avenue De Lafayette, Boston, MA
The price is CA $251 per night from Jul 20 to Jul 21
CA $251
CA $341 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,551 reviews)
2 day boston speed visit
"Great location for everything historic, Boston common or theater. Close to many T stops for further parts of Boston."

Reviewed on Jul. 8, 2025

Hyatt Regency Boston
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 $318 per night from Aug 1 to Aug 2
CA $318
CA $418 total
Aug 1 - Aug 2
includes taxes & fees
8.6/10 Excellent! (2,822 reviews)
"Things were great."

Reviewed on Jul. 9, 2025

Omni Parker House
See all 3,703 properties in Downtown Crossing
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 Downtown Crossing vacation package cost?
Perhaps less than you might think --- from a low CA $907, actually! By bundling flights, hotels and car rentals into a custom-built travel package, your Downtown Crossing escape is just a few clicks away.
How do I get a cheap travel package to Downtown Crossing?
Combine your bookings with Expedia to save big bucks on your next adventure. With over 550 airlines and 1,000,000 hotels across the globe, your Downtown Crossing vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not throw in some interesting tours and experiences? It's an easy way to unlock even more savings. Your dream vacation in Downtown Crossing is much closer than you thought!
Where should I stay in Downtown Crossing?
Vacationers come from all over the world to see Fenway Park and TD Garden in Downtown Crossing. Book a room near these terrific attractions to make sightseeing a breeze.
What are the top hotels in Downtown Crossing?
Luxury At A 2br/2ba | 200mbps Internet and Centralized Downtown Location | On are a couple of the most well-known hotels in Downtown Crossing. Why not have a look at the rates and amenities at each and then make up your mind?
How far in advance should I book my Downtown Crossing vacation?
Smart travelers often book as early as possible. You can generally browse through international fares on Expedia up to 12 months before your flight. If you're booking last minute, fear not. Cheap prices occasionally become available in the last weeks before departure.
What does an Expedia Downtown Crossing travel package include?
Flights, car rentals and hotels --- we bring you the very best bargains. All you have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to create an awesome Downtown Crossing getaway.
What should I know before booking a Downtown Crossing travel package?
Locking in all the parts of your vacation together is one of the best ways to save. Bundle your airfares, rental cars and hotels into a neat package. But it's not just hotels. Expedia has all kinds of properties, including vacation rentals such as beachside villas and spacious residences. The list is almost endless!
Can I choose my airline with a Downtown Crossing Expedia vacation package?
With a vacation package, you're the boss. Whether you're eager to fly to Downtown Crossing in business or coach, simply choose from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Downtown Crossing vacation package?
Yes, you can. We totally understand that even the best-laid plans can go awry, so we're here to help if you have to make changes to your Downtown Crossing vacation package. It may be possible to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Things to do

Boston's Best Freedom Trail Walking Tour

Boston's Best Freedom Trail Walking Tour

CA $34
per adult
92% of travellers recommend
Boston's Best Freedom Trail Walking Tour
Boston: Iconic Food Tasting & History Tour - Downtown

Boston: Iconic Food Tasting & History Tour - Downtown

CA $172
per adult
100% of travellers recommend
Boston: Iconic Food Tasting & History Tour - Downtown
Italian Dinner with Tiramisu Finale in Boston

Italian Dinner with Tiramisu Finale in Boston

CA $164
per adult
Italian Dinner with Tiramisu Finale in Boston
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.