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

Chatham

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

Gloucester

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

Hyannis

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

Plymouth

Plymouth

Where to stay in Massachusetts

Find the best Massachusetts areas for the activities you enjoy most.Learn more about Massachusetts
Learn more about Massachusetts
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 stone walls and pointed towers.
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.

Back Bay

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

A waterfront with a large white cruise ship docked, a building with a green dome, and a blue banner.
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.

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 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 street sign for Charles St.
Photo by Greater Boston Convention & Visitors Bureau
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.

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 Boston Harbor or Old North Church while you're visiting, and jump aboard the metro at Aquarium to get around town.

Things to do in Massachusetts

Massachusetts is ideal for outdoor and romantic getaways, offering a plethora of activities such as skiing, music concerts, and scenic tours. Visitors can explore numerous museums, partake in unique experiences, and enjoy festive holiday markets and Halloween celebrations. The vibrant culture and stunning landscapes make it a perfect destination for those seeking adventure and charm.

Shopping

Experience the Burlington Mall, a vibrant shopping centre with diverse stores and family-friendly entertainment. Visit Hebert's Candy Mansion for delightful treats, and explore the Solomon Pond Mall, another bustling shopping hub offering a mix of shops and activities for all ages in Massachusetts.

Recreation

Tsongas Arena offers a vibrant atmosphere for sports enthusiasts, while Foxborough Country Club invites you to unwind on its picturesque golf course amidst nature. For entertainment, Paradise Rock Club provides an engaging musical experience, perfect for relaxation and enjoyment in a lively setting.

Adventure

Experience the thrill of skiing at Wachusett Mountain Ski Area, where snow-covered slopes await adventurous skiers. Visit the Apex Entertainment Center for family-friendly arcade fun and excitement. Don't miss the charming Flying Horses Carousel, offering delightful outdoor rides perfect for families seeking a whimsical adventure.

Nightlife

Experience the vibrant nightlife in Massachusetts at Cambridge Common, a charming pub perfect for a romantic evening. For a more casual vibe, visit Park-9 Dog Bar, where you can enjoy a lively atmosphere with friends and unwind with a drink after a long day of exploring.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Massachusetts

Massachusetts is perfect for outdoor enthusiasts and romantic getaways, featuring a blend of stunning scenery and rich history. Visitors can explore beautiful beaches, urban parks, and renowned colleges and universities. The diverse attractions cater to those seeking cultural experiences, family-friendly activities, and opportunities to immerse themselves in nature, making it an ideal destination for every type of traveller.

  • Fenway Park: Experience the thrill of America’s pastime at this historic sports stadium, renowned for its vibrant atmosphere and rich baseball heritage. Enjoy the iconic Green Monster and immerse yourself in the culture of Boston sports.
  • Harvard University: Stroll through the prestigious grounds of one of the world’s oldest universities. Explore its stunning architecture and lush gardens, while soaking in the intellectual culture that has shaped countless leaders and innovators.
  • Boston Museum of Fine Arts: Discover a vast collection of art spanning centuries and cultures at this acclaimed museum. From Impressionist masterpieces to contemporary works, the museum offers a cultural feast for art enthusiasts.

Best time to go to Massachusetts

The best time to visit Massachusetts is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January and February are its coolest month on average. At the time of February, visitor numbers are average and weather is mostly sunny.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.3°F (-2.6°C)Light RainMostly SunnySlightly LowSlightly Low
February27.3°F (-2.6°C)Light RainMostly SunnyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostly SunnyAverageAverage
April47.5°F (8.6°C)Light RainMostly SunnySlightly HighAverage
May58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
June63.3°F (17.400000000000002°C)Light RainMostly SunnySlightly HighAverage
July69.4°F (20.8°C)Light RainMostly SunnySlightly HighSlightly High
August70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
September62.4°F (16.900000000000002°C)Light RainMostly SunnyAverageAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageSlightly High
November38.8°F (3.8°C)Light RainMostly SunnySlightly LowAverage
December33.6°F (0.9°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Massachusetts

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Massachusetts.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Massachusetts

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
S$415
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (4,845 reviews)
"Frequently stay here"

Reviewed on 26 Sept, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
S$393
25 Oct - 26 Oct
includes taxes & fees
Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
S$350
25 Oct - 26 Oct
includes taxes & fees
9/10 Wonderful! (2,926 reviews)
"Unique room design that torrents out to be just great for our group of three. Conveniently located to everything."

Reviewed on 26 Sept, 2026

The Revolution Hotel
See all 17,943 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)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
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A historic building with a clock tower, a large gate, and a well-maintained lawn.

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 public park with a large fountain, surrounded by trees and modern buildings.

Boston Common

9.4/10 (18,299 reviews)
The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.
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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 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 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

S$63
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

S$90
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

S$47
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.