A large stone church with a tall bell tower and arched windows.

Great Barrington Vacations from US$ 492

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The Latest Great Barrington Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
    17 Dec - 19 Dec

    Lodges At Cresthaven + Flight

    Lake George
    2 nights
    4.0 star property
    9.4/10 - Exceptional (667 reviews)
    "My husband and I really enjoyed the stay at this hotel. We were stunned on how beautiful the property was, especially inside the hotel room. Everything was immaculate. We will absolutely be staying here again ❤️ we cannot wait to plan our next adventure here to the Lodges at Cresthaven ❤️"
    Reviewed November 1, 2026
    Roundtrip • New York (JFK) - Albany (ALB)
    JFK - ALB • 1 stop ALB - JFK • 1 stop
    US$ 634
    US$ 492
    per traveler
    found 23 hours ago
    Lodges At Cresthaven
  • A log cabin interior with a stone fireplace, wooden furniture, and large windows.
    21 Dec - 26 Dec

    Brook Bound Inn + Flight

    Wilmington
    5 nights
    2.0 star property
    9.4/10 - Exceptional (22 reviews)
    "The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in."
    Reviewed October 19, 2026
    Roundtrip • Orlando (MCO) - Albany (ALB)
    MCO - ALB • 1 stop ALB - MCO • 1 stop
    US$ 1,472
    US$ 1,132
    per traveler
    found 4 hours ago
    Brook Bound Inn
  • A modern kitchen with white cabinetry, a wooden table, and a large window providing a view of the outdoors.
    25 Dec - 27 Dec

    Charming 6 Bdrm Countryside Stay + Flight

    Great Barrington
    2 nights
    3.0 star property
    Roundtrip • New York (NYC) - Albany (ALB)
    LGA - ALB • 1 stop ALB - LGA • Nonstop
    US$ 2,571
    US$ 2,252
    per traveler
    found 6 hours ago
    Charming 6 Bdrm Countryside Stay
  • A covered patio area with a wicker sofa, a round table with drinks, and a chair.
    21 Dec - 26 Dec

    The Equinox Golf Resort And Spa + Flight

    Manchester Village Historic District
    5 nights
    4.5 star property
    7.4/10 - Good (680 reviews)
    "RLoved the Equinox…."
    Reviewed November 4, 2026
    Roundtrip • Orlando (MCO) - Albany (ALB)
    MCO - ALB • 1 stop ALB - MCO • 1 stop
    US$ 1,185
    US$ 1,043
    per traveler
    found 4 hours ago
    The Equinox Golf Resort And Spa
  • A large, historic building with a symmetrical facade, multiple windows, and a central entrance with steps.
    14 Jan - 17 Jan

    The Stockade Inn + Flight

    Stockade Historic District
    3 nights
    2.0 star property
    9.4/10 - Exceptional (230 reviews)
    Roundtrip • Houston (IAH) - Albany (ALB)
    IAH - ALB • 1 stop ALB - IAH • 1 stop
    US$ 813
    US$ 717
    per traveler
    found 1 day ago
    The Stockade Inn

Where to stay in Great Barrington

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Learn more about Great Barrington

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Lake Mansfield Park

9.0/10 (22 reviews)
This serene 29-acre lake offers swimming, boating, and fishing amid a conservation forest. Enjoy the sandy beach and shaded picnic areas, or explore wildlife along accessible walking trails through the adjacent woodland.
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Great Barrington Hotel Deals

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
2.4 km from Great Barrington
8.8 out of 10, Excellent, (854 reviews)
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
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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.