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 Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Price was CA $1,063, price is now CA $755 per person
CA $755
per person
Apr 2 - Apr 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,111 reviews)
Clean. Spacious room. Comfortable bed. Great location.

Reviewed on Feb 7, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,305, price is now CA $2,095 per person
CA $2,095
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Ottawa (YOW) 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

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,384, price is now CA $1,736 per person
CA $1,736
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) 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

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,885, price is now CA $1,400 per person
CA $1,400
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) 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

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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb 22 to Feb 23
CA $140
CA $219 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (3,103 reviews)
Room Nice and clean, but small.

Reviewed on Feb 11, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $145 per night from Feb 24 to Feb 25
CA $145
CA $169 total
Feb 24 - Feb 25
includes taxes & fees
9.2/10 Wonderful! (6,220 reviews)
Excellent Hotel in a great location with a subway station right next to the front entrance. Would highly recommend

Reviewed on Feb 11, 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Feb 17 to Feb 18
CA $108
CA $126 total
Feb 17 - Feb 18
includes taxes & fees
9/10 Wonderful! (2,451 reviews)
I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ...

Reviewed on Feb 7, 2026

The Revolution Hotel
See all 4,151 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 $755. 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

Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 reviews)

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
Boston's Zakim Bridge

TD Garden

4.5/5(240 reviews)

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

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

Fenway Park

4.5/5(305 reviews)

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

Fenway Park

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
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 $108
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 $31
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.