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.
3-night Berkshire County vacations
Price found within the past 48 hours. Click for updated prices.
5-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.
TPA
Tampa
BDL
Hartford
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
MCO
Orlando
BDL
Hartford
$68 Roundtrip, just found
$68
Roundtrip
just found
FLL
Fort Lauderdale
BDL
Hartford
$69 Roundtrip, found 20 hours ago
$69
Roundtrip
found 20 hours ago
Top rated hotels for your Berkshire County vacation
Hotel Downstreet
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
18.68 mi from city center
The price is $144 per night
$144
includes taxes & fees
$129 per night
Jan 8 - Jan 9
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum of Contemporary Art.
Pool
Hot Tub
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
4.55 mi from city center
The price is $99 per night
$99
includes taxes & fees
$89 per night
Jan 20 - Jan 21
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
3.33 mi from city center
The price is $115 per night
$115
includes taxes & fees
$103 per night
Jan 15 - Jan 16
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and Company.
Pool
Hot Tub
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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
Hotels
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Flights
Packages
Popular Berkshire County vacation package destinations
^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.