Downtown Crossing Vacation Packages

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Top Holiday Package Deals in Downtown Crossing

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,004, price is now CA $517 per person
CA $517
per person
Oct 28 - Oct 30
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,838, price is now CA $1,683 per person
CA $1,683
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug. 26, 2025

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 1 day 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

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Price was CA $2,192, price is now CA $1,405 per person
CA $1,405
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug. 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,123, price is now CA $1,373 per person
CA $1,373
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop 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

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 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

Downtown Crossing Hotel Deals

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Sep 1 to Sep 2
CA $224
CA $261 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (2,713 reviews)
"It was a nice little hotel that was out-of-the-way in terms of the hustle and bustle downtown Boston, but still within walking distance to go eat somewhere nice and do some sightseeing. I was there for business, but I would definitely go back there for pleasure as well."

Reviewed on Aug. 24, 2025

Club Quarters Hotel Faneuil Hall, Boston
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $346 per night from Sep 1 to Sep 2
CA $346
CA $451 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (2,924 reviews)
Perfect place in Boston!
"This is a great hotel is in an excellent location!"

Reviewed on Aug. 25, 2025

Omni Parker House
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
The price is CA $313 per night from Aug 31 to Sep 1
CA $313
CA $429 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (4,337 reviews)
Our Go To
"This is our second stay at The Godfrey Hotel in Boston. We returned due to the location, the comfort of the rooms and the staff. Bonus- the attached restaurant RUKA is amazing!"

Reviewed on Aug. 25, 2025

The Godfrey Hotel Boston
See all 3,730 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.
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Frequently asked questions

How much does a Downtown Crossing vacation package cost?
Perhaps less than you might think — from a low CA $517, 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: 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 $165
per adult
Italian Dinner with Tiramisu Finale in Boston
Haunted Boston Ghost Tours

Haunted Boston Ghost Tours

CA $34
per adult
Haunted Boston Ghost Tours
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.