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
Price was CA $1,222, price is now CA $775 per person
CA $775
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (2,439 reviews)
It's a 2 star hotel disguised as 3.5

Reviewed on Jul 4, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,613, price is now CA $1,039 per person
CA $1,039
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $10,513, price is now CA $6,809 per person
CA $6,809
per person
Aug 5 - Aug 12
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $5,034, price is now CA $3,335 per person
CA $3,335
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (432 reviews)
Terrible experience. Family of five with three youngsters. Despite being loyal to the MO brand for years, this Boston property is by far one of the worst we have stayed at. To start, there were blood stains on the room carpet. Two rooms on the same floor were confirmed by staff when the booking was made, yet they were not available at check-in. Room service trays sat outside of rooms for hours without being collected. The bathroom was outdated, and the air conditioning was noisy. Overall, the property looked more like a Holiday Inn than a Mandarin Oriental. We will never come back.

Reviewed on Jun 30, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,176, price is now CA $802 per person
CA $802
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 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
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

4.5/5(197 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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $226 per night from Aug 2 to Aug 3
CA $226
CA $305 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,410 reviews)
"The chef at the restaurant prepared an incredible menu of delicious and exotic combinations that leave you wanting more. The prices are high, but the portions are large and leave you feeling that your exquisite dining was worth paying more."

Reviewed on Jul 4, 2026

Hyatt Regency Boston/Cambridge
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 $268 per night from Jul 26 to Jul 27
CA $268
CA $361 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,514 reviews)
"Great location . Friendly staff Lots of super dining choices within 10 minutes walking. Easy free bus ride from the airport, a block off the water."

Reviewed on Jul 4, 2026

Seaport Hotel 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 $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,711 reviews)
"The location was good. The price was good. I didn’t realize the bathroom and shower were down the hall. That was a little inconvenient."

Reviewed on Jul 3, 2026

The Revolution Hotel
See all 4,182 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 $775. 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.

Stay near popular Dudley Square attractions

Urban League Boston

Learn about the local history of Boston when you take a trip to Urban League Boston. Take in the museums while you're in the area.
See properties

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
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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.