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A coastal village with houses, a lighthouse, and boats on the water.

Massachusetts Vacation Packages

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Top destinations in Massachusetts

A street lined with historic buildings, including the Union Oyster House and Yankee Publishing Building.
FlightsHotels

Boston

Boston

Top Massachusetts vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Coffee/tea maker, full-size fridge, microwave, oven
    Sept 7 - Sept 9

    Boston Lodge and Suites + Flight

    Dorchester
    2 nights
    4.0 star property
    8.4/10 - Very good (190 reviews)
    "Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles."
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Boston (BOS)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,218
    CA $665
    per traveller
    found 1 day ago
    Boston Lodge and Suites
  • Indoor pool
    Sept 6 - Sept 12

    Pier 7 Condominiums + Flight

    Bass River
    6 nights
    2.0 star property
    8.4/10 - Very good (16 reviews)
    "Ac unit was leaking"
    Reviewed August 6, 2026
    Roundtrip • Montreal (YUL) - Boston (BOS)
    YUL - BOS • Nonstop BOS - YUL • 1 stop
    CA $1,307
    CA $855
    per traveller
    found 15 hours ago
    Pier 7 Condominiums
  • Blackout drapes, iron/ironing board, cribs (surcharge)
    Sept 6 - Sept 12

    Harbor Hotel Provincetown + Flight

    Provincetown
    6 nights
    3.0 star property
    8.2/10 - Very good (1,013 reviews)
    Roundtrip • Montreal (YUL) - Provincetown (PVC)
    YUL - BOS • Nonstop BOS - YUL • 1 stop
    CA $1,839
    CA $1,218
    per traveller
    found 15 hours ago
    Harbor Hotel Provincetown
  • Terrace/patio
    Oct 1 - Oct 4

    The Whitney Hotel + Flight

    Beacon Hill
    3 nights
    4.0 star property
    9.6/10 - Exceptional (601 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $1,887
    CA $1,251
    per traveller
    found 1 day ago
    The Whitney Hotel
  • Suite, Multiple Beds (John Adams Presidential Suite)
    Oct 9 - Oct 12

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,007 reviews)
    "The rooms were impeccable, and the staff was excellent. They were very proactive and helpful in resolving a few challenges we experienced during our trip. The overall experience and the attention given to toddlers and children were amazing. It is also worth mentioning that even the crib was excellent, which made our stay much more comfortable. We truly appreciated the level of service and attention to detail."
    Reviewed August 5, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $2,921
    CA $1,992
    per traveller
    found 1 day ago
    Boston Harbor Hotel

Discover the most popular places to visit in Massachusetts

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.

What to do in Massachusetts

Boston Hop-On Hop-Off Trolley Tour

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

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
See all activities in Massachusetts

Massachusetts Hotel Deals

Bar (on property)

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
29.2 km from Massachusetts
9.4 out of 10, Exceptional, (2,445 reviews)
The price is CA $311
CA $362 total
includes taxes & fees
Sep 6 - Sep 7
Hyatt Place Boston/Seaport District
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.
See all properties in Massachusetts

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 $665. 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.

Book with confidence

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.

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.

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.