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 marina with various boats docked, a wooden pier, and houses in the background.

Hyannis

Hyannis
A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Gloucester

Gloucester

Our guide on where to stay in Massachusetts

Find the best Massachusetts areas for the activities you enjoy most.
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

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 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

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

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

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

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

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 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

The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Boston Harbor or New England Aquarium while you're visiting, and jump aboard the metro at Aquarium to get around town.

Our pick of the best Massachusetts Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
NZ$432
20 Sept - 21 Sept
includes taxes & fees
9.6/10 Exceptional! (4,969 reviews)
"It was a great experience to spend time"

Reviewed on 7 Sept 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$284
13 Sept - 14 Sept
includes taxes & fees
9/10 Wonderful! (2,900 reviews)
"Second time staying at the Revolution hotel and will stay again in the future. We do the community restrooms and not a big deal at all. Especially love the coffee shop(Kohi) for the morning fill and Cosmica for evening bites."

Reviewed on 7 Sept 2026

The Revolution Hotel
Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
NZ$623
4 Oct - 5 Oct
includes taxes & fees
9.6/10 Exceptional! (4,174 reviews)
"Pay a lot money for the room no breakfast, very poor for me, never stay again, very disappointed"

Reviewed on 7 Sept 2026

Encore Boston Harbor
See all 18,195 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 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 park with manicured hedges, flowering plants, and a city skyline in the background.

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 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 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 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 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 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 acclaimed art galleries 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$82
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$119
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

NZ$62
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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.