Massachusetts Vacations & Trips 2026 from CA $741

Your Massachusetts Vacation

Our Massachusetts vacation packages provide an affordable, easy and engaging way to experience all that this exciting destination has to offer. If it's dining and culture you're after, this is the place to be. A trip to Massachusetts wouldn't be complete without exploring some of its most well-known cities, starting with Boston. A couple of the top attractions here include Fenway Park and TD Garden. Hyannis is another favourite city with Massachusetts travellers. Visitors to this destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. Expedia has everything you need when it comes to planning your Massachusetts vacation. From hotels and flights, to activities and more, we know how to curate a travel experience like no other.

Top vacation destinations in Massachusetts

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

Top Massachusetts Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Lakeside Inn

CA $741

per person

Dec 24 - Dec 28

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.2/10 Very good! (1,038 reviews)

Four Seasons Hotel Boston

Bay Village

CA $1,614

per person

Jan 29 - Feb 1

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.4/10 Exceptional! (491 reviews)

The Langham, Boston

Downtown Boston

CA $1,156

per person

Dec 15 - Dec 18

found 2 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,003 reviews)

Raffles Boston

Back Bay

CA $1,452

per person

Jan 8 - Jan 10

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.6/10 Exceptional! (343 reviews)

Great hotel and a great team

Reviewed on Nov 1, 2026

Eurostars The Boxer

West End

CA $792

per person

Dec 15 - Dec 18

found 2 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

8.8/10 Excellent! (1,636 reviews)

Where to stay in Massachusetts

Find the best Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Massachusetts

Quincy Market with an American flag, historic buildings, and a clock tower in the background.

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.

Find hotel + flight trips in Downtown Boston

A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

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.

Find hotel + flight trips in Back Bay

A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

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.

Find hotel + flight trips in Seaport District

A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

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.

Find hotel + flight trips in Beacon Hill

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

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.

Find hotel + flight trips in North End

Things to do in Massachusetts

Massachusetts offers a perfect blend of outdoor adventures and romantic getaways, making it an ideal destination for tourists. You can enjoy activities like skiing and music concerts, along with numerous day trips to explore its rich history. The state is home to many attractions, including family-friendly museums and beautiful scenery, ensuring a memorable experience for all visitors.

Shopping

In Massachusetts, explore the vibrant Harvard Square for a mix of shopping and entertainment. For unique finds, visit Raynham Flea Market. Don't forget to stop by Tony's Bakery for delightful treats to take home as souvenirs.

Recreation

At Gillette Stadium, immerse yourself in the energetic sports atmosphere while enjoying a variety of events. The New England Sports Center offers thrilling ice skating experiences for adventure seekers. For a peaceful retreat, visit Waterfront Promenade Park, where you can relax and rejuvenate amidst serene surroundings.

Adventure

At Cape Codder Water Park, dive into thrilling water slides and enjoy family-friendly attractions in a vibrant atmosphere. Explore the scenic Deer Island HarborWalk, perfect for outdoor enthusiasts seeking picturesque views. For a fun-filled evening, head to Orleans Bowling Center, where excitement and adventure await in a lively arcade environment.

Nightlife

Experience the vibrant nightlife of Massachusetts at Cambridge Common, a lively pub perfect for drinks and romance. Alternatively, unwind at Park-9 Dog Bar, where you can enjoy a unique atmosphere that blends fun and relaxation, making it an ideal spot for a memorable evening out.

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

Find the best attractions in Massachusetts

Massachusetts offers a perfect blend of outdoor activities, scenic beauty, and romantic getaways, making it ideal for various travellers. Key attractions include beautiful beaches, urban parks, and national/state parks, catering to those seeking cultural experiences and family-friendly adventures. Be sure to explore the best attractions in the area to fully enjoy your vacation in this charming state.

Fenway Park: Experience the rich history of Fenway Park, one of the oldest baseball stadiums in the U.S. with its iconic Green Monster. Feel the electric atmosphere during a Red Sox game, and soak in the cultural significance of this landmark.
Harvard University: Walk through the historic campus of Harvard University, the oldest institution of higher learning in the U.S. Explore its beautiful architecture, vibrant student life, and art collections, while immersing yourself in the scholarly vibe.
TD Garden: Attend a thrilling event at TD Garden, known for hosting major sports, concerts, and conferences. Enjoy the modern amenities and vibrant atmosphere, making it a hub of excitement in the heart of Boston.

Best time to go to Massachusetts

The best time to visit Massachusetts can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Massachusetts falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Massachusetts falls in January and February. February has average visitor numbers and mostly sunny weather.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	27.3°F (-2.6°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	27.3°F (-2.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Average	Average
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.3°F (14.6°C)	Light Rain	Mostly Sunny	Average	Average
June	63.3°F (17.400000000000002°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	70.7°F (21.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	62.4°F (16.900000000000002°C)	Light Rain	Mostly Sunny	Average	Average
October	56.7°F (13.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	33.6°F (0.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly 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.

Massachusetts Hotel Deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $183

CA $270 total

Nov 22 - Nov 23

includes taxes & fees

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $148

CA $172 total

Nov 25 - Nov 26

includes taxes & fees

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $171

CA $247 total

Nov 26 - Nov 27

includes taxes & fees

9.6/10 Exceptional! (5,168 reviews)

"I usually do not like to leave negative reviews but I feel I have no choice in the matter. I arrived for a 2 night stay in a King Harbor Suite on Saturday afternoon around 3:30pm. Check in was swift and effortless, but when arriving at the room, there was hair in the sink, a backed up sink, and 2 ..."

Reviewed on Nov 4, 2026

See all 17,614 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 CA $741. 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.