Cheap Vacations in The Berkshires
- The Berkshires vacations
- 3-night The Berkshires vacations
- 4-night The Berkshires vacations
- 5-night The Berkshires vacations
- 6-7 night The Berkshires vacations
3-night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
4-night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
5-night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to The Berkshires
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
TPA
Tampa
BDL
Hartford
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
MCO
Orlando
BDL
Hartford
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
FLL
Fort Lauderdale
BDL
Hartford
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Top rated hotels for your The Berkshires vacation
Hotel Downstreet
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
36.81 mi from city center
The price is $144 per night
$144
includes taxes & fees
$129 per night
Nov 18 - Nov 19
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.
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.41 mi from city center
The price is $121 per night
$121
includes taxes & fees
$108 per night
Nov 18 - Nov 19
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
17.41 mi from city center
The price is $108 per night
$108
includes taxes & fees
$97 per night
Nov 24 - Nov 25
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.
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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More ways to book
^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.