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 Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Aug. 28 - Sep. 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (189 reviews)
The grounds are well kept. The staff are very friendly and helpful. The building itself is tired. The kitchenette had no utensils and only paper cups. Also the hot plate didn’t have a place to plug in. The fridge and microwave worked though and that’s all we needed. Just a heads up in case you need more. They had a variety of breakfast options that are included. Pancakes, waffles, eggs, muffins etc. For the price, we were happy.

Reviewed on Jun. 3, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Great hotel. Very accommodating!

Reviewed on Jun. 6, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
This is a beautiful hotel with a great gym and first class service. The housekeeping team is world class.

Reviewed on Jun. 5, 2024

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
Jul. 25 - Jul. 29
just found
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (155 reviews)
From the moment we walked into the lobby at Beacon Hill Hotel we were greeted and treated like VIPs. The room, was a corner, looking out over Charles Street. Perfectly comfortable and artfully appointed. My only complaint and this is silly the pillows too puffy. We dined there as well and the food and service was superb.

Reviewed on May 23, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 27 - Aug. 30
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (32 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 2024

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 which includes night scenes and a city 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 hotel + flight trips in Downtown Boston

Dudley Square Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jul. 5 to Jul. 6
CA $232
CA $310 total
includes taxes & fees
Jul 5 - Jul 6
9/10 Wonderful! (2,150 reviews)
"The room was very modern, stylish and comfortable."

Reviewed on Jun. 4, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jul. 4 to Jul. 5
CA $232
CA $318 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,687 reviews)
"Had a wonderful stay here and will definitely be a returning guest 😊"

Reviewed on Jun. 5, 2024

Omni Parker House
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 $196 per night from Jun. 16 to Jun. 17
CA $196
CA $228 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,512 reviews)
"Best property to stay at in Boston. Absolutely immaculate. You can walk anywhere from hotel."

Reviewed on Jun. 3, 2024

The Revolution Hotel
See all 3,214 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.

Explore other types of vacation packages

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 $1,137. 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

Image for Fenway Park

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
Image for Harvard University

Harvard University

4.5/5(279 reviews)

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

Harvard University
Image for Boston Common

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

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $294
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.