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New Scotland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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The Latest New Scotland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Oct 12 - Oct 16

    Berkshire Mountain Lodge + Flight

    Pittsfield
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,024 reviews)
    "Staff was great!!"
    Reviewed July 25, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $891
    CA $717
    per traveller
    found 7 hours ago
    Berkshire Mountain Lodge
  • Exterior
    Oct 12 - Oct 16

    The Whitlock + Flight

    Lenox
    4 nights
    2.0 star property
    8.4/10 - Very good (338 reviews)
    "Very nice coffee set up in the morning. Staff was super courteous and helpful. Most of property is updated although carpeting and rugs are tired. Location is great, very convenient to Tanglewood and restaurants. Parking is onsite and more than ample. B"
    Reviewed July 25, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,334
    CA $1,022
    per traveller
    found 7 hours ago
    The Whitlock
  • Front of property
    Oct 12 - Oct 16

    Gedney Farm + Flight

    Great Barrington
    4 nights
    3.5 star property
    9.2/10 - Wonderful (139 reviews)
    "Pet friendly and amazing grounds"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,312
    CA $1,015
    per traveller
    found 7 hours ago
    Gedney Farm
  • Lobby
    Oct 12 - Oct 16

    Vacation Village in the Berkshires + Flight

    Williamstown
    4 nights
    3.0 star property
    8.8/10 - Excellent (2,474 reviews)
    "It was a nice room with a beautiful location, and the pools were well maintained. However, the front desk was repeatedly grumpy whenever we had a question. Even saying good morning was met with an indifferent tone. For example, the washer didn't work (rinse cycle didn't work) and when I reported it in order to help the next person who would use it, they didn't seem interested and were put off. Additionally, the keys consistently didn't work until after several times, and whenever we tried to..."
    Reviewed July 24, 2026
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $911
    CA $726
    per traveller
    found 7 hours ago
    Vacation Village in the Berkshires
  • Lobby lounge
    Oct 12 - Oct 16

    Berkshires Untold + Flight

    Lenox
    4 nights
    3.5 star property
    9.0/10 - Wonderful (1,011 reviews)
    Roundtrip • Toronto (YYZ) - Albany (ALB)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,113
    CA $917
    per traveller
    found 7 hours ago
    Berkshires Untold
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.