A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

Berkshire County Vacations & Trips from $273

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Your Berkshire County Vacation

With a Berkshire County vacation package, you can forget about the stress of planning and simply focus on experiencing what this exciting destination has on offer. Kick off your trip to Berkshire County with a few nights in Lenox visiting popular attractions like National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another city that draws crowds from far and wide. Massachusetts Museum of Contemporary Art and Mount Greylock are two of the leading places to see in this destination. If you're ready to stop daydreaming and start doing, Expedia will help turn your Berkshire County vacation into reality.

Top destinations in Berkshire County

A large white house with multiple chimneys, surrounded by lush greenery and trees.
FlightsHotels

Lenox

Lenox

The Latest Berkshire County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a sofa, a coffee table, a desk with a chair, a TV, and a bed with a headboard.
    Jan 22 - Jan 24

    Best Western Hartford Hotel & Suites + Flight

    South Meadows
    2 nights
    2.5 star property
    7.8/10 - Good (1,100 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $340
    $273
    per traveler
    found 1 day ago
    Best Western Hartford Hotel & Suites
  • An outdoor dining area with tables set for two, wooden beams, and hanging light fixtures.
    Jan 22 - Jan 24

    Delamar West Hartford + Flight

    West Hartford
    2 nights
    4.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $800
    $584
    per traveler
    found 1 day ago
    Delamar West Hartford
  • A large white building with a steep roof, surrounded by trees and a small pond.
    Jan 15 - Jan 18

    Brook Bound Inn + Flight

    Wilmington
    3 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 • Los Angeles (LAX) - Albany (ALB)
    LAX - ALB • 1 stop ALB - LAX • 1 stop
    $1,051
    $833
    per traveler
    found 23 hours ago
    Brook Bound Inn
  • A room with wooden paneling, a piano, a chair, and a door leading to another room.
    Dec 31 - Jan 4

    South Shire + Flight

    Bennington
    4 nights
    4.0 star property
    9.0/10 - Wonderful (141 reviews)
    Roundtrip • Tampa (TPA) - Albany (ALB)
    TPA - ALB • 1 stop ALB - PIE • Nonstop
    $1,139
    $960
    per traveler
    found 1 day ago
    South Shire
  • A rooftop patio with outdoor seating, a view of a lake, and string lights.
    Dec 16 - Dec 22

    The Landing Hotel at Rivers Casino Schenectady + Flight

    Nothside
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,001 reviews)
    Roundtrip • Orlando (MCO) - Albany (ALB)
    MCO - ALB • Nonstop ALB - MCO • 1 stop
    $1,085
    $919
    per traveler
    found 13 hours ago
    The Landing Hotel at Rivers Casino Schenectady

Discover the most popular places to visit in Berkshire County

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.
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Berkshire County Hotel Deals

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

The Yankee Inn
2.5 star property
3.3 mi from Berkshire County
9.2 out of 10, Wonderful, (1,004 reviews)
"Everything about this place was wonderful! The location, the staff, the cleanliness. The only downsize was we booked this property because of the pool and it was under maintenance during my stay. A notice would have been nice :( Other than that, beautiful inn."
$126 nightly
The price is $141
Dec 12 - Dec 13
Total with taxes and fees
The Yankee Inn
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.