Massachusetts Vacations & Trips

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Top destinations in Massachusetts

Quincy Market showing a city, an administrative buidling and heritage architecture
FlightsFlightsHotelsHotels

Boston

Boston
Nantucket which includes cbd, boating and a small town or village
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Nantucket

Nantucket

Where to stay in Massachusetts

Find the best Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Massachusetts
Downtown Boston which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(2,415 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

Massachusetts Hotel Deals

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is ￥16,804 per night from Jan 11 to Jan 12
￥16,804
￥19,568 total
Jan 11 - Jan 12
includes taxes & fees
9.2/10 Wonderful! (6,125 reviews)
everything was great!

Reviewed on Jan 8, 2026

Harborside Inn Of Boston
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is ￥18,593 per night from Jan 18 to Jan 19
￥18,593
￥26,358 total
Jan 18 - Jan 19
includes taxes & fees
8.4/10 Very Good! (1,263 reviews)
Great breakfast, comfortable rooms.

Reviewed on Jan 7, 2026

Hilton Boston Back Bay
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 ￥24,694 per night from Jan 25 to Jan 26
￥24,694
￥35,191 total
Jan 25 - Jan 26
includes taxes & fees
9/10 Wonderful! (4,390 reviews)
Spotless rooms

Reviewed on Jan 5, 2026

Omni Boston Hotel at the Seaport
See all 17,417 properties in Massachusetts
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 Massachusetts vacation package cost?
Chart your own course with our Massachusetts vacation packages, which start from only . Select the flights and hotels that suit your style. Then, add on a couple of tours or activities for an incredible adventure.
How do I get a cheap travel package to Massachusetts?
Creating your own Massachusetts vacation package with Expedia is a smart way to save. We have access to more than 550 airlines and 1,000,000 hotel options spread across the globe. With such a wonderful range to choose from, you'll have no issues putting together your perfect escape.
Where should I stay in Massachusetts?
Boston is a terrific place to include in your itinerary. This is where you'll find impressive sights such as Fenway Park and Boston Common. Cambridge also lures many jetsetters eager to check out some of the best attractions in Massachusetts. Included in these are Harvard Square and Harvard University.
What are the top hotels in Massachusetts?
Look up Hampton Inn Boston - Logan Airport and Boston Park Plaza. They're the first choice for many travelers headed to Boston. If Provincetown is on your itinerary, Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel are both popular options.
How far in advance should I book my Massachusetts vacation?
It's difficult to pick the best time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, don't stress. Bargain prices occasionally appear just weeks before departure dates.
What does an Expedia Massachusetts travel package include?
That's up to you. You can choose from a variety of Massachusetts bundles, such as a flight, rental car and hotel. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your dream Massachusetts break looks like, you're sure to save!
What should I know before booking a Massachusetts travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and score terrific discounts. You're not restricted to hotels, however. We have oceanfront condos, rural cottages and everything in between!
Can I choose my airline with a Massachusetts Expedia vacation package?
You can, and with over 550 airlines to pick from around the world, you have plenty of choice. Browse the available options and find out which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Massachusetts vacation package?
We understand — unexpected stuff happens. If you've locked in a Massachusetts vacation package and need to change or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to cancel or amend your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.

Discover the most popular places to visit in Massachusetts

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

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

Fenway Park
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

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
Harvard University showing a city and heritage architecture

Harvard University

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

Harvard University

What to do in Massachusetts

Hear the legendary true stories of Revolutionary Bostonians like Paul Revere, Midnight Rider at the Old North Church

Boston: Freedom Trail History Small Group Walking Tour

￥5,496
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

￥5,323
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

￥4,541
per adult
100% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
See all activities in Massachusetts

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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.