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.
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 6 hours ago
$68
Roundtrip
found 6 hours ago
FLL
Fort Lauderdale
BDL
Hartford
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
MCO
Orlando
BDL
Hartford
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day 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
Dec 19 - Dec 20
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
Free Cancellation
Reserve now, pay when you stay
16.41 mi from city center
The price is $99 per night
$99
includes taxes & fees
$89 per night
Jan 6 - Jan 7, 2025
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 Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
11.5 mi from city center
The price is $133 per night
$133
includes taxes & fees
$119 per night
Jan 1 - Jan 2, 2025
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
Pool
Spa
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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Flights
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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.