Cheap Vacations in Berkshire County
- Berkshire County vacations
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Berkshire County vacations
Price found within the past 48 hours. Click for updated prices.
4-night Berkshire County vacations
Price found within the past 48 hours. Click for updated prices.
Top places to visit in Berkshire County
Lenox
Flight deals to Berkshire County
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
SJU
San Juan
BDL
Hartford
$122 Roundtrip, found 17 hours ago
$122
Roundtrip
found 17 hours ago
PIE
St. Petersburg
ALB
Albany
$172 Roundtrip, found 5 days ago
$172
Roundtrip
found 5 days ago
FLL
Fort Lauderdale
BDL
Hartford
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Top rated hotels for your Berkshire County vacation
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
8 mi from city center
$128 nightly
The price is $143 total per night
$143 total
Nov 1 - Nov 2
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 Summit Triple.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
2.7 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Nov 16 - Nov 17
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.
The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
3.33 mi from city center
$106 nightly
The price is $118 total per night
$118 total
Nov 1 - Nov 2
Total with taxes and fees
Located in Lenox, The Yankee Inn is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
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See all available properties in Berkshire County
View all propertiesLowest 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.
Top Picks
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^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 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.
