Dudley Square Holidays

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Your Dudley Square Holiday

Book a Dudley Square holiday package and immerse yourself in the atmosphere and rhythm of this captivating neighbourhood. With all your travel plans worked out, the only thing you need to focus on here is living your best life. When it's time to head out and explore, you'll find a lot of awesome attractions nearby including Fenway Park, Boston Common and Faneuil Hall Marketplace. Tick off one, two or all during your trip to Dudley Square. Expedia can help turn your ideal Dudley Square holiday into reality, whatever your travel plans or budget.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Our guide on 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 a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotel + flight trips in Downtown Boston

Our pick of the best Dudley Square Hotel Deals

Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is AU$296 per night from 20 Dec to 21 Dec
AU$296
includes taxes & fees
20 Dec - 21 Dec
9.6/10 Exceptional! (2,589 reviews)
"Amazing"

Reviewed on 20 Nov. 2024

Seaport Hotel Boston
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
The price is AU$290 per night from 8 Dec to 9 Dec
AU$290
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,290 reviews)
"My go to when visit my child at college"

Reviewed on 24 Nov. 2024

Hilton Boston Park Plaza
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 AU$334 per night from 27 Nov to 28 Nov
AU$334
includes taxes & fees
27 Nov - 28 Nov
8.6/10 Excellent! (2,860 reviews)
"I couldn’t be more impressed with the level of service. From the moment I arrived the front desk staff went above and beyond to make me feel welcome. Check-in was smooth and efficient. Throughout my stay, the entire staff always responded and assisted promptly and kindly."

Reviewed on 20 Nov. 2024

Omni Parker House
See all 3,320 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Dudley Square holiday package cost?
Live it up in Dudley Square from as little as . 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 holiday 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 holiday 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 holiday 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 holiday 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 favourites.
How far in advance should I book my Dudley Square holiday?
Get rewarded with the widest variety at the lowest prices by booking your Dudley Square holiday 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 holiday!
What does an Expedia Dudley Square travel package include?
Expedia has all you need to organise 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 holiday package lets you plan your escape your way. Plus, you’ll get access to great discounts when you combine your accommodation 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 holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday 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 holiday 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 which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

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

Fenway Park
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 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
New England Aquarium

New England Aquarium

4/5(7 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Activities

Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$115
Per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Mysteries & Murders of Salem Guided Night-Time Walking Tour

Mysteries and Murders of Salem Guided Night-Time Walking Tour

AU$51
Per adult
92% of travellers recommend
Mysteries and Murders of Salem Guided Night-Time Walking Tour
Boston: Guided Walking Tour of the Freedom Trail

Boston: Guided Walking Tour of the Freedom Trail

AU$48
Per adult
98% of travellers recommend
Boston: Guided Walking Tour of the Freedom Trail
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.