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

Nantucket

Nantucket
A white house with a red roof on a grassy hill.

Provincetown

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

Chatham

Chatham
A large house by the water with several boats.

Falmouth

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

Hyannis

Hyannis
A row of colorful, historic houses with a central path.

Oak Bluffs

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

Gloucester

Gloucester
A white church with a steeple and clock, surrounded by trees and a signboard.

South Yarmouth

South Yarmouth

Where to stay in Massachusetts

Find the best Massachusetts areas 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

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.

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

Gourmet restaurants interesting history and top sights from Copley Square to Newbury Street – discover Back Bay, a destination also famous for its 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

Travellers to Seaport District praise its captivating waterfront views. If you've got some more time to explore, be sure to stop by Boston Harbor and Liberty Wharf.

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

Historical sites, shopping and restaurants highlight some notable features of Beacon Hill. Make a stop by Acorn Street or Charles Street while you're visiting, and jump aboard the metro at Charles-MGH Station or Park St. Station to get around town.

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.

Top hotels in Massachusetts

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
4.929.101 ₫
6.629.288 ₫ total
20 Sept - 21 Sept
includes taxes & fees
9.6/10 Exceptional! (4,934 reviews)
"Seaport is in a great spot. Close to the harbor and not to far from downtown Boston."

Reviewed on 3 Sept 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
3.548.150 ₫
4.131.947 ₫ total
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (2,883 reviews)
"Clean bathrooms"

Reviewed on 2 Sept 2026

The Revolution Hotel
Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
8.560.094 ₫
9.561.625 ₫ total
4 Oct - 5 Oct
includes taxes & fees
Encore Boston Harbor
See all 18,214 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 1null000null000 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)
Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.
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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)
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 fascinating museums.
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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)
After visiting Boston Common, make a plan to see the other sights and activities in Boston. Discover the fascinating museums in this vibrant area or seek out the local tours.
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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)
You can learn about the local history of Boston during your trip to a well-known site such as Copley Square. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
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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 acclaimed theatre 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 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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