Dudley Square Vacation Packages

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Top Holiday Package Deals in Dudley Square

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $1,085, price is now CA $725 per person
CA $725
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,156 reviews)
Gym had equipment that didn't work.

Reviewed on Sep 11, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,262, price is now CA $1,270 per person
CA $1,270
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep 2, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $2,320, price is now CA $1,526 per person
CA $1,526
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
Lou the driver was awesome and very informative. We enjoyed walking to Harvard Yard which is only two blocks away! So much fun for family’s.

Reviewed on Sep 6, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,664, price is now CA $1,754 per person
CA $1,754
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,122 reviews)
This is my favorite hotel to stay at. The location is the best for walkers, diners, shopping, everything. Staff is super helpful and warm.

Reviewed on Sep 9, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $2,395, price is now CA $1,597 per person
CA $1,597
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (593 reviews)
The window coverings were inadequate for sleeping, the property across the street kept all their lights on until 11pm which shown like a daytime sun fully illuminating the entire apartment. Also, the shower design in the master caused water to go all over the floor during a shower. Friday night there were very loud motorcycles up and down the street until late into the night. Other nights it was nicely quiet. Otherwise, the property was good ---

Reviewed on Sep 9, 2025

Where to stay in Dudley Square

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

Dudley Square Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $333 per night from Sep 22 to Sep 23
CA $333
CA $394 total
Sep 22 - Sep 23
includes taxes & fees
9.6/10 Exceptional! (3,381 reviews)
"Quiet location. Close to public transportation to get all around Boston! Free bikes to explore."

Reviewed on Sep. 10, 2025

Seaport Hotel Boston
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 $327 per night from Sep 21 to Sep 22
CA $327
CA $438 total
Sep 21 - Sep 22
includes taxes & fees
9/10 Wonderful! (3,950 reviews)
"It was a nice hotel and great shower pressure"

Reviewed on Sep. 9, 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 $310 per night from Sep 21 to Sep 22
CA $310
CA $362 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (3,755 reviews)
"Very sleek!"

Reviewed on Sep. 10, 2025

citizenM Boston North Station
See all 3,759 properties in Dudley Square
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 Dudley Square vacation package cost?
Live it up in Dudley Square from as little as CA $725. We offer a great selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add some tours or activities to your vacation package.
How do I get a cheap travel package to Dudley Square?
Bundle, bundle, bundle. Hotels, rental cars and flights — combine whatever you need into a Dudley Square vacation package to save a pile of cash. Score even more deals when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to tailor your vacation your own way. We offer more than 550 air carriers and 1,000,000 properties across the globe, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Dudley Square?
Make sightseeing easier by staying someplace near Dudley Square's fantastic attractions. Fenway Park and TD Garden are two visitor favorites.
How far in advance should I book my Dudley Square vacation?
Get rewarded with the widest variety at the lowest prices by booking your Dudley Square vacation early. Airlines tend to sell flights anywhere up to 12 months prior to departure, so start locking things in ASAP. That being said, Expedia is committed to providing you with the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Dudley Square travel package include?
Expedia has all you need to organize your Dudley Square escape, but what goes into your package is your choice. Select from any combination of hotels, rental cars and flights. Looking for some activities or tours to keep you entertained? Once you've made your booking, you can add them too. Whatever your budget, there's a package deal to match your needs.
What should I know before booking a Dudley Square travel package?
Whether it's adventure or relaxation you're seeking, a Dudley Square vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Dudley Square Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Dudley Square vacation package?
If your travel plans in Dudley Square have been upended, it's a relief to know that you can cancel or amend your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Dudley Square

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

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 $75
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.