Massachusetts Holidays

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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 boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham

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

Nantucket

Nantucket
A modern building with a sign reading "THE HANOVER Theatre" and a decorative fountain in front.

Worcester

Worcester
A city skyline at night with illuminated buildings reflecting on the water.

Foxborough

Foxborough
A street with a restaurant named "Pebbles Restaurant" and a nearby clothing store.

Plymouth

Plymouth

Our guide on where to stay in Massachusetts

Find the best Massachusetts areas for the activities you enjoy most.
Quincy Market with an American flag, historic buildings, and a clock tower in the background.
Quincy Market with its neoclassical architecture, including columns and a prominent sign.
A historic building with a clock tower, surrounded by modern skyscrapers.
A cityscape with historic buildings, including a prominent clock tower and a modern skyscraper.
Quincy Market with a prominent clock tower, American flag, and a street vendor area.

Downtown Boston

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.
A historic building with intricate architecture, a modern skyscraper, and a fountain in a park.
A historic building with intricate architecture, large arched windows, and statues in front.
A historic red brick building with ornate detailing and a clock tower, located at a busy intersection with modern buildings and traffic.
A city skyline with sailboats on a calm body of water.

Back Bay

Parisian boulevards and elegant brownstones conjure a truly romantic atmosphere, perfect for strolling and window shopping.

A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.
A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.
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.

Seaport District

Join excited crowds enjoying harbor-side views, Revolutionary War-era landmarks, as well as superb restaurants and museums along this thriving waterfront.

A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.
A large building with a golden dome, red brick walls, and white columns.
A large building with a golden dome, red brick columns, and a staircase leading to the entrance.
A cityscape with a prominent golden dome building, surrounded by lush greenery and a river in the background.
A narrow alley with cobblestone path, brick buildings, and climbing ivy.

Beacon Hill

Take a walk through the charming streets, historic buildings and small-town atmosphere of Boston’s oldest and wealthiest suburbs.

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.
A historic street with red brick buildings, a prominent church steeple, and a clear blue sky.
A metal plaque with the inscription "BOSTON TRAIL" and a decorative emblem.
A brick building with a sign for the Paul Revere House Museum.
A cityscape with a river, historic buildings, and a prominent tower.

North End

The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Old North Church or Paul Revere House while you're visiting, and jump aboard the metro at Aquarium to get around town.

Our pick of the best Massachusetts Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$449
22 Nov - 23 Nov
includes taxes & fees
9.2/10 Wonderful! (4,922 reviews)
"Wonderful"

Reviewed on 22 Oct 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
NZ$212
23 Nov - 24 Nov
includes taxes & fees
The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
NZ$356
23 Nov - 24 Nov
includes taxes & fees
9.6/10 Exceptional! (5,137 reviews)
"Very clean rooms, great variety at breakfast buffet, nice bar, helpful and accommodating staff."

Reviewed on 22 Oct 2026

Seaport Hotel Boston
See all 17,900 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 holiday package cost?
Chart your own course with our Massachusetts holiday 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 holiday 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 travellers 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 holiday?
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 holiday 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 holiday package?
We understand — unexpected stuff happens. If you've locked in a Massachusetts holiday 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)
The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.
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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 theatre scene.
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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)
You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.
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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)
Historic buildings, great shopping and bags of local colour – what’s not to love about Copley Square?
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A public park with a large fountain, surrounded by trees and modern buildings.

Boston Common

9.4/10 (18,299 reviews)
Trace the history of Boston and take a break from the city heat in the USA’s oldest public park.
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A historic town square with brick buildings, a red bus, and a Harvard sign.

Harvard Square

9.0/10 (3,936 reviews)
With a visit to Harvard Square, a favourite shopping spot in Cambridge, you can browse for souvenirs. Experience the fascinating museums and acclaimed art galleries 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 in Boston Convention and Exhibition Center, a top convention centre in Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
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What to do in Massachusetts

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

NZ$86
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

NZ$124
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

NZ$63
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
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.