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.
Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $881, price is now CA $589 per person
CA $589
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (30 reviews)
Very impressed! Very clean, friendly staff, felt safe, the room was far bigger than expected, I’ll be back!

Reviewed on Sep. 1, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,572, price is now CA $1,444 per person
CA $1,444
per person
Nov 5 - Nov 8
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep. 2, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,229, price is now CA $2,596 per person
CA $2,596
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.

Reviewed on Sep. 3, 2025

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $1,510, price is now CA $1,001 per person
CA $1,001
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
It was a great experience. A bit small for four people in one room. But we made due.

Reviewed on Sep. 2, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Price was CA $1,531, price is now CA $1,046 per person
CA $1,046
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
7.4/10 Good! (89 reviews)
Had a 4 night stay at the Maverick Suites on Temple Street. I mainly booked this room to be close to my daughter, who lives a couple of doors down. The room is a bit tight for two people, but my friend & I made it work by sleeping 90 degrees on the double bed to turn it into more of a "short king". Room was very clean, however the one suggestion I would make is to use less of the strong-smelling cleaner (Fabioso?) or a more natural cleaner. Otherwise, the property felt safe and clean. Beautiful hardwood floors, nice bathroom & small kitchen area. Staff is very responsive via TEXT (not by phone). We requested clean towels etc, and they were very accommodating. Temple St. is walkable to many sites you'll want to check out in Boston via a walk or to the Park St T station. I would recommend staying at the Maverick Suites!

Reviewed on Jun. 25, 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

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 $357 per night from Sep 5 to Sep 6
CA $357
CA $464 total
Sep 5 - Sep 6
includes taxes & fees
Omni Parker House
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 $313 per night from Sep 21 to Sep 22
CA $313
CA $364 total
Sep 21 - Sep 22
includes taxes & fees
Club Quarters Hotel Faneuil Hall, Boston
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 $458 per night from Sep 5 to Sep 6
CA $458
CA $597 total
Sep 5 - Sep 6
includes taxes & fees
The Godfrey Hotel Boston
See all 3,724 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 $589, 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

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
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
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.