Dudley Square Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Downtown Boston

4.5/5(95 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 Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in Dudley Square

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 6.099.887 ₫ per night from 25 May to 26 May
6.099.887 ₫
8.002.186 ₫ total
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (4,357 reviews)
I didn’t have breakfast.

Reviewed on 17 May 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 3.340.116 ₫ per night from 25 May to 26 May
3.340.116 ₫
3.889.565 ₫ total
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,612 reviews)
Great location

Reviewed on 17 May 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is 4.722.278 ₫ per night from 29 May to 30 May
4.722.278 ₫
6.573.243 ₫ total
29 May - 30 May
includes taxes & fees
9.2/10 Wonderful! (4,648 reviews)
No problem everything was fine

Reviewed on 17 May 2026

Omni Boston Hotel at the Seaport
See all 4,211 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.

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 1null000null000 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.

Popular places to visit

Fenway Park

Fenway Park

4.5/5(62 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University

Harvard University

4.5/5(104 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University
Gillette Stadium

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium