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

Berkshire County Vacations & Trips from $406

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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 Candlewood Suites hotel with a modern design, featuring multiple floors and a well-lit entrance.
    Jan 15 - Jan 18

    Candlewood Suites Windsor Locks Bradley Arpt by IHG + Flight

    Windsor Locks
    3 nights
    2.5 star property
    8.4/10 - Very good (1,241 reviews)
    "I called before booking the room to ask if they have shuttle service to and from Hartford Airport because the website said it stopped before my 11:44pm arrival. I called when I had my luggage and they said to catch the LazFly shuttle! That is not the hotel shuttle and it took 25 minutes to get to the hotel after dropping people at car rental and passenger parking lot! Needing a ride to the airport the next morning I asked about their shuttle when I checked in….Eileen, desk attendant told me it..."
    Reviewed November 8, 2026
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $493
    $406
    per traveler
    found 1 day ago
    Candlewood Suites Windsor Locks Bradley Arpt by IHG
  • An outdoor dining area with tables and chairs, surrounded by plants and trees.
    Jan 15 - Jan 18

    Delamar West Hartford + Flight

    West Hartford
    3 nights
    4.0 star property
    9.8/10 - Exceptional (1,003 reviews)
    "best overnight stay ever, loved every thing about this property"
    Reviewed November 5, 2026
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • 1 stop BDL - SJU • Nonstop
    $1,150
    $785
    per traveler
    found 1 day ago
    Delamar West Hartford
  • A buffet setup with various food items in metal containers, a sign indicating 'Cheese Omelet', and a patterned wall in the background.
    Jan 15 - Jan 18

    Holiday Inn Express Vernon - Manchester by IHG + Flight

    Vernon
    3 nights
    2.5 star property
    8.6/10 - Excellent (1,004 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • 1 stop BDL - SJU • Nonstop
    $586
    $469
    per traveler
    found 1 day ago
    Holiday Inn Express Vernon - Manchester by IHG
  • A large, two-story house with a wrap-around porch, a central entrance, and a flag.
    Dec 24 - Dec 28

    Belden House & Mews + Flight

    Litchfield Historic District
    4 nights
    5.0 star property
    9.4/10 - Exceptional (14 reviews)
    "Absolutely beautiful property. The restaurant was amazing and delicious. The room was perfect and cozy and the staff, from the front desk to the restaurant, were all on point! Highly, highly, highly recommend and would return again."
    Reviewed November 2, 2026
    Roundtrip • Orlando (MCO) - Hartford (BDL)
    MCO - BDL • Nonstop BDL - MCO • Nonstop
    $1,735
    $1,430
    per traveler
    found 0 hours ago
    Belden House & Mews
  • A modern conference room with wooden flooring, grey sofas, a blue ottoman, and a flat-screen TV on the wall.
    Jan 15 - Jan 18

    Trumbull Apartments + Flight

    Downtown Hartford
    3 nights
    3.0 star property
    2.0/10 - (1 review)
    "Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
    Reviewed September 1, 2026
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $715
    $598
    per traveler
    found 1 day ago
    Trumbull Apartments

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)
"As soon as you walked in the staff was friendly & helpful. Place was very clean. Pool & hot tub was also very clean. The sunset overlooking the pond was awesome. My wife and I spend a couple mini weekend getaways & this was a great one. Also can't beat the breakfast to start the day. Thanks Again Joe"
$111 nightly
The price is $124
Nov 15 - Nov 16
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.