Cheap Vacations in Berkshire County

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Top places to visit in Berkshire County

Lenox which includes an administrative buidling
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Lenox

Lenox

Flight deals to Berkshire County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, May 7 - Mon, May 11
MCO
Orlando
BDL
Hartford
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando to Hartford, returning Mon, May 11, priced at $100 found 2 days ago
Fri, Apr 10 - Mon, Apr 13
ATL
Atlanta
BDL
Hartford
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Atlanta to Hartford, returning Mon, Apr 13, priced at $114 found 1 day ago
Thu, May 7 - Fri, May 29
MCO
Orlando
ALB
Albany
$141 Roundtrip, found 1 day ago
$141
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando to Albany, returning Fri, May 29, priced at $141 found 1 day ago

Top rated hotels for your Berkshire County vacation

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
8 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Mar 8 - Mar 9
Total with taxes and fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
2.7 mi from city center
$121 nightly
The price is $136 total per night
$136 total
Apr 2 - Apr 3
Total with taxes and fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
18.06 mi from city center
$197 nightly
The price is $220 total per night
$220 total
Mar 5 - Mar 6
Total with taxes and fees
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Pet friendly
Parking included
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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 all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.