Downtown Crossing Vacation Packages

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  • Better together

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

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Top Holiday Package Deals in Downtown Crossing

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,424, price is now CA $942 per person
CA $942
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,157, price is now CA $2,327 per person
CA $2,327
per person
Apr 27 - May 1
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $4,358, price is now CA $2,939 per person
CA $2,939
per person
Apr 29 - May 3
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Attention to guest needs.

Reviewed on Feb 8, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $1,818, price is now CA $1,254 per person
CA $1,254
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,560, price is now CA $1,080 per person
CA $1,080
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

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

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 $164 per night from Feb 15 to Feb 16
CA $164
CA $254 total
Feb 15 - Feb 16
includes taxes & fees
9.4/10 Exceptional! (4,904 reviews)
The staff was extremely friendly and accommodating. The decor was beautiful. The room was very clean and comfortable.

Reviewed on Feb 6, 2026

The Godfrey Hotel Boston
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
One Avenue De Lafayette Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Mar 2 to Mar 3
CA $173
CA $248 total
Mar 2 - Mar 3
includes taxes & fees
9/10 Wonderful! (1,848 reviews)
Wonderful location. Self park garage attached to hotel. Large rooms. Nice lobby and bar. Walking distance to Boston Common, North End and many wonderful places.

Reviewed on Feb 8, 2026

Hyatt Regency 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 $201 per night from Feb 12 to Feb 13
CA $201
CA $281 total
Feb 12 - Feb 13
includes taxes & fees
8.8/10 Excellent! (3,304 reviews)
Arriving in Boston was a bit stressful with traffic and tight roads. Valet staff was incredibly helpful. Porters (or bellhops) were attentive and polite. Checking in was a breeze. Overall, I loved the room, area and history of the Omni Parker. Definitely recommend if you plan on staying in ...

Reviewed on Feb 10, 2026

Omni Parker House
See all 4,198 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
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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 $942, 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 Hop-On Hop-Off Trolley Tour

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

CA $73
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 $110
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $32
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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.