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

Eastern Massachusetts Adventure Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Adventure vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
  • Aug 24 - Aug 27

    Hotel AKA Back Bay + Flight

    Back Bay
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,302 reviews)
    Roundtrip Buffalo (BUF) - Boston (BOS)
    BUF - BOSNonstop BOS - BUFNonstop
    CA $1,095
    CA $869
    per traveller
    found 1 day ago
    Hotel AKA Back Bay
  • Aug 24 - Aug 27

    The Langham, Boston + Flight

    Downtown Boston
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    "Great hotel in Boston. central to everything."
    Reviewed July 20, 2026
    Roundtrip Buffalo (BUF) - Boston (BOS)
    BUF - BOSNonstop BOS - BUFNonstop
    CA $1,708
    CA $1,207
    per traveller
    found 1 day ago
    The Langham, Boston
  • Sept 24 - Sept 28

    Ramada by Wyndham Boston + Flight

    Dorchester
    4 nights
    2.5 star property
    6.8/10 - (1,804 reviews)
    Roundtrip Toronto (YYZ) - Boston (BOS)
    YYZ - BOSNonstop BOS - YYZNonstop
    CA $1,091
    CA $901
    per traveller
    found 17 hours ago
    Ramada by Wyndham Boston
  • Sept 21 - Sept 25

    Studio Allston Hotel + Flight

    Brighton
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,295 reviews)
    Roundtrip Halifax (YHZ) - Boston (BOS)
    YHZ - BOS1 stop BOS - YHZ1 stop
    CA $1,452
    CA $1,218
    per traveller
    found 18 hours ago
    Studio Allston Hotel
  • Oct 12 - Oct 15

    Wyndham Boston Beacon Hill + Flight

    West End
    3 nights
    3.5 star property
    7.8/10 - Good (2,156 reviews)
    Roundtrip Buffalo (BUF) - Boston (BOS)
    BUF - BOSNonstop BOS - BUFNonstop
    CA $1,375
    CA $1,169
    per traveller
    found 1 day ago
    Wyndham Boston Beacon Hill

Discover the most popular places to visit in Eastern Massachusetts

What to do in Eastern Massachusetts

Top Adventure Eastern Massachusetts Hotels

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.

Find awesome Eastern Massachusetts adventure vacations

How can I book the best Eastern Massachusetts adventure trips?

Choose your own adventure in Eastern Massachusetts, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Eastern Massachusetts family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Eastern Massachusetts. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Eastern Massachusetts adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Eastern Massachusetts adventure vacation for couples?

Book a Eastern Massachusetts couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Eastern Massachusetts?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Eastern Massachusetts with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Eastern Massachusetts adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

What types of mountain accommodations are available in Eastern Massachusetts?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Eastern Massachusetts. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.