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 Vacations from $496

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Your Eastern Massachusetts Vacation

Choose one of our vacation packages to Eastern Massachusetts and wander wherever your inner adventurer desires. Dining and culture are just a couple of the things you can look forward to in this exciting destination. Your trip to Eastern Massachusetts wouldn't be complete without experiencing some of its most well-known cities, starting with Boston. Two of the top attractions here include Fenway Park and TD Garden. Hyannis is another favorite city with Eastern Massachusetts travelers. Visitors to this exciting destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. From the instant you book your Eastern Massachusetts vacation to when you get back home, Expedia will be with you each step of the way.

The Latest Eastern Massachusetts Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A glass-fronted fireplace with visible logs and flames, set on a wooden floor.
    Dec 11 - Dec 14

    Boston Lodge and Suites + Flight

    Dorchester
    3 nights
    4.0 star property
    8.4/10 - Very good (194 reviews)
    "The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."
    Reviewed October 17, 2026
    Roundtrip • Austin (AUS) - Boston (BOS)
    AUS - BOS • Nonstop BOS - AUS • Nonstop
    Save 100% on your flight
    $1,017
    $496
    per traveler
    found 1 day ago
    Boston Lodge and Suites
  • A multi-story building with a curved corner, large windows, and a brick facade.
    Jan 28 - Feb 2

    Eurostars The Boxer + Flight

    West End
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,635 reviews)
    "We would consider staying here again, but for the price there are probably better options nearby. It was conveniently located near the train station and room views were neat!"
    Reviewed November 7, 2026
    Roundtrip • Austin (AUS) - Boston (BOS)
    AUS - BOS • Nonstop BOS - AUS • Nonstop
    $878
    $589
    per traveler
    found 1 day ago
    Eurostars The Boxer
  • A lobby with a central round table, potted plants, and artwork on the walls.
    Dec 23 - Dec 26

    Mandarin Oriental, Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (468 reviews)
    "Overall Excellent! clean room, very nice staff"
    Reviewed November 4, 2026
    Roundtrip • Austin (AUS) - Boston (BOS)
    AUS - BOS • Nonstop BOS - AUS • 2 stops
    $1,828
    $1,272
    per traveler
    found 1 day ago
    Mandarin Oriental, Boston
  • A park with a lamp post, a bridge, and buildings in the background.
    Dec 10 - Dec 13

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Roundtrip • Austin (AUS) - Boston (BOS)
    AUS - BOS • Nonstop BOS - AUS • Nonstop
    $1,650
    $1,153
    per traveler
    found 1 day ago
    The Newbury Boston
  • A beachside hotel with a balcony overlooking the ocean, a pool area, and a beach with umbrellas.
    Dec 21 - Dec 26

    Ashworth by the Sea + Flight

    Hampton Beach
    5 nights
    3.0 star property
    8.4/10 - Very good (1,441 reviews)
    Roundtrip • Austin (AUS) - Boston (BOS)
    AUS - BOS • Nonstop BOS - AUS • 2 stops
    $858
    $614
    per traveler
    found 1 day ago
    Ashworth by the Sea

Discover the most popular places to visit in Eastern 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.
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What to do in Eastern Massachusetts

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

$50
per adult
0% of travelers recommend
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
See all activities in Eastern Massachusetts

Eastern Massachusetts Hotel Deals

A spacious hotel lobby with a high ceiling, a bar area, and a seating area with a sofa and ottomans.

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor
3.0 star property
4.7 mi from Eastern Massachusetts
8.4 out of 10, Very good, (1,004 reviews)
"Great location and staff is so welcoming and helpful!!"
$171 nightly
The price is $191
Nov 8 - Nov 9
Total with taxes and fees
Hotel 1620 Plymouth Harbor
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 Eastern Massachusetts
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.