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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Aug 27 - Sep 3
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
While the property was clean and the staff knowledgeable and kind, the marketing including representation of a pool and arcade. While a pool is on site, it’s run by a fitness club. The hours provided by the hotel are meaningless as the fitness club will close the pool to hotel guests allowing their members pool access. The pool restrictions are those of the fitness club. Our adult daughter could not swim with our 10 year old as their specifications of an adult are age 21. The arcade was not open during our two day stay. While a nice hotel, not recommended with children. They do offer a water park for $30/person per day. This is open Fri-Sun.

Reviewed on Jul. 25, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
Aug 27 - Sep 3
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
Beautiful hotel in a great location

Reviewed on Jul. 18, 2025

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
per person
Aug 27 - Sep 3
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.4/10 Very Good! (3,247 reviews)
Convenient location. Close to everything. Shopping to the left, shopping to the right. Beautiful, clean hotel. Friendly staff. I got an early check-in which is always convenient. My room was quiet. I will definitely book this hotel again in the future.

Reviewed on Jul. 23, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Friendly and professional service and care. Great location to walk to every site you need to get to. Staff especially Will and Howard (door men) always friendly and asked if you needed anything Thanks to the staff you made our first but not our last stay amazing

Reviewed on Jul. 25, 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

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 $250 per night from Aug 24 to Aug 25
CA $250
CA $347 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,716 reviews)
"This property is in a perfect location in the Seaport. We loved it!"

Reviewed on Jul. 24, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Aug 10 to Aug 11
CA $258
CA $300 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,487 reviews)
"Great place. Just be prepared that there is no curb drop off or hotel parking, so figure out how you are going to park and get your suitcases there ahead of time. Very modern, good restaurant/coffee bar and large hangout lobby, 10 min walk to Finway area. Highly recommend."

Reviewed on Jul. 23, 2025

citizenM Boston Back Bay
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 $237 per night from Aug 24 to Aug 25
CA $237
CA $276 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,578 reviews)
"It was wicked awesome"

Reviewed on Jul. 24, 2025

citizenM Boston North Station
See all 3,741 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.
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Frequently asked questions

How much does a Dudley Square vacation package cost?
Live it up in Dudley Square from as little as CA $969. 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 $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
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 $46
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.