Massachusetts Vacations & Trips

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Top destinations in Massachusetts

A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.

Boston

Boston
A harbor with boats, waterfront houses, and an American flag.

Nantucket

Nantucket

Where to stay in Massachusetts

Find the best Massachusetts areas and neighborhoods for the activities you enjoy most.Learn more about Massachusetts
Learn more about Massachusetts
A nighttime street scene with illuminated trees, a market stall, and historic buildings.
Quincy Market with an American flag, historic buildings, and a clock tower in the background.
A spacious indoor area with a high, arched ceiling and brick walls. There are multiple tables and chairs arranged for seating.
A busy urban street lined with historic theaters, cafes, and modern buildings.
Quincy Market with its neoclassical architecture, including columns and a prominent sign.

Downtown Boston

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.

A historic building with ornate architecture, a staircase, and a tree in front.
A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.
A street scene with a building displaying a 'SALE' sign, a 'Crane & Co. Paper Makers' sign, and a staircase leading to the entrance.
A grand library with high ceilings, arched windows, and rows of tables and chairs.
A historic building with intricate architecture, a modern skyscraper, and a fountain in a park.

Back Bay

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A large, illuminated ship docked at a pier with fireworks in the background.
A city skyline at night with illuminated buildings reflecting on the water.
A city skyline at dusk with illuminated buildings and a calm river.
A city skyline with tall buildings and a waterfront.
A waterfront cityscape at dusk with illuminated buildings and a calm river.

Seaport District

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A brick building with a flag, a street lamp, and greenery.
A narrow alley with brick buildings, green ivy, and street lamps.
A red brick building with a white entrance and a stone wall with a number 81.
A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.
A brick building with black shutters and an American flag.

Beacon Hill

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.
A tree-lined street with a prominent white church steeple in the background.
A church interior with rows of pews, a large organ, and American flags.
A historic street with red brick buildings, a prominent church steeple, and a clear blue sky.
A street sign with multiple directional arrows pointing to various destinations.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Massachusetts Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
₩261,844
₩352,163 total
Sep 20 - Sep 21
includes taxes & fees
9.6/10 Exceptional! (4,873 reviews)
"Great location. Safe and clean. Perfect view of the harbor. Only complaint is they need to lose the automated phone call line when trying to reach the bellman or front desk. Called for bags using their robot and it never connected to a live human. Human touch is key in customer service. So lose the ..."

Reviewed on Aug 27, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
₩302,704
₩408,787 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (4,808 reviews)
"Great hotel!"

Reviewed on Aug 27, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
₩177,977
₩207,254 total
Aug 30 - Aug 31
includes taxes & fees
The Revolution Hotel
See all 18,179 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.

Stay near popular Massachusetts attractions

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
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A classical building with columns and a blue door, surrounded by trees and people walking.

Harvard University

9.2/10 (6,542 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
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A park with manicured hedges, flowering plants, and a city skyline in the background.

Boston Common

9.4/10 (18,299 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.
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A soccer stadium with a crowd of spectators, a goalpost, and players in action.
Photo by The Curious Zephyr

Gillette Stadium

9.0/10 (1,182 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
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A modern building with 'GARDEN' signage, a waterfront, and a cable-stayed bridge.

TD Garden

9.2/10 (7,449 reviews)
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
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A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.

Copley Square

9.4/10 (7,327 reviews)
Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.
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A nighttime street scene with a historic building, street lamps, and a church spire.

Harvard Square

9.0/10 (3,936 reviews)
With a visit to Harvard Square, a favorite shopping spot in Cambridge, you can search for that perfect souvenir. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
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A modern architectural building with a large overhanging roof and a glass facade.

Boston Convention and Exhibition Center

8.8/10 (2,207 reviews)
During your trip, find out what's happening at Boston Convention and Exhibition Center, a top convention center in Boston. Experience the acclaimed art scene or attend a sporting event in this vibrant area.
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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.