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
Lenox
Williamstown
Great Barrington
Pittsfield
Stockbridge
North Adams
Lee
Hancock
Adams
The Latest Berkshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Best Western Hartford Hotel & Suites
Jan 22 - Jan 24Best Western Hartford Hotel & Suites + Flight
South Meadows2 nights2.5 star property7.8/10 - Good (1,100 reviews)Roundtrip • San Juan (SJU) - Hartford (BDL)SJU - BDL • Nonstop BDL - SJU • Nonstop$340$273found 1 day agoper traveler - Delamar West Hartford
Jan 22 - Jan 24Delamar West Hartford + Flight
West Hartford2 nights4.0 star property9.8/10 - Exceptional (1,001 reviews)Roundtrip • San Juan (SJU) - Hartford (BDL)SJU - BDL • Nonstop BDL - SJU • Nonstop - Hotel Kinsley
Dec 27 - Jan 2Hotel Kinsley + Flight
Stockade District6 nights3.5 star property8.8/10 - Excellent (416 reviews)Roundtrip • San Juan (SJU) - Albany (ALB)SJU - JFK • Nonstop LGA - SJU • Nonstop - Holiday Inn Express Vernon - Manchester by IHG
Dec 23 - Dec 31Holiday Inn Express Vernon - Manchester by IHG + Flight
Vernon6 nights2.5 star property8.6/10 - Excellent (1,002 reviews)Roundtrip • Phoenix (PHX) - Hartford (BDL)PHX - BDL • 1 stop BDL - PHX • 1 stop$938$771found 1 day agoper traveler - Simsbury 1820 House
Dec 23 - Dec 31Simsbury 1820 House + Flight
Simsbury Center6 nights4.0 star property9.4/10 - Exceptional (1,003 reviews)Roundtrip • Phoenix (PHX) - Hartford (BDL)PHX - BDL • 1 stop BDL - PHX • 1 stop$1,204$993found 1 day agoper traveler
Discover the most popular places to visit in Berkshire County
Berkshire County Hotel Deals
9.2 out of 10, Wonderful, (1,004 reviews)
9.2/10
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
$141 total
Dec 12 - Dec 13
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
9 mi from Berkshire County
9.2 out of 10, Wonderful, (1,003 reviews)
9.2/10
Wonderful
(1,003 reviews)
$107 nightly
The price is $120
$120 total
Dec 6 - Dec 7
Total with taxes and fees
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South2.5 star property
10.5 mi from Berkshire County
8.6 out of 10, Excellent, (1,001 reviews)
8.6/10
Excellent
(1,001 reviews)
$85 nightly
The price is $95
$95 total
Dec 6 - Dec 7
Total with taxes and fees
9.6 out of 10, Exceptional, (986 reviews)
9.6/10
Exceptional
(986 reviews)
$112 nightly
The price is $125
$125 total
Nov 29 - Nov 30
Total with taxes and fees
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"The property is in excellent condition and the room was as advertised. Very close to town. Please note, there is no staff on site so everything is self check-in and self service."
$188 nightly
The price is $210
$210 total
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG2.5 star property
17 mi from Berkshire County
8.8 out of 10, Excellent, (861 reviews)
8.8/10
Excellent
(861 reviews)
$90 nightly
The price is $101
$101 total
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox2.5 star property
3.5 mi from Berkshire County
9.0 out of 10, Wonderful, (1,002 reviews)
9.0/10
Wonderful
(1,002 reviews)
"Could not complain about anything. The entire property was light, bright, clean and well maintained!"
$108 nightly
The price is $121
$121 total
Dec 15 - Dec 16
Total with taxes and fees
Vacation Village in the Berkshires
Vacation Village in the Berkshires3.0 star property
8 mi from Berkshire County
8.8 out of 10, Excellent, (2,853 reviews)
8.8/10
Excellent
(2,853 reviews)
"Big place,nice indoor pool with arcade. Fireplace in the suite and nice balcony on 2nd floor units. Really close to Jimney Peak"
$108 nightly
The price is $121
$121 total
Nov 16 - Nov 17
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.