Cheap Vacations in The Berkshires

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Flight deals to The Berkshires

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

Fri, Jan 16 - Sun, Jan 18
MCO
Orlando
BDL
Hartford
$69 Roundtrip, found 6 days ago
$69
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Orlando to Hartford, returning Sun, Jan 18, priced at $69 found 6 days ago
Thu, Feb 26 - Sun, Mar 1
ATL
Atlanta
BDL
Hartford
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Atlanta to Hartford, returning Sun, Mar 1, priced at $118 found 4 days ago
Wed, Jan 21 - Sun, Jan 25
ORD
Chicago
BDL
Hartford
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jan 21 from Chicago to Hartford, returning Sun, Jan 25, priced at $124 found 1 day ago

Top rated hotels for your The Berkshires 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
28.42 mi from city center
$111 nightly
The price is $124 total per night
$124 total
Dec 7 - Dec 8
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
17.93 mi from city center
$108 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
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
37.59 mi from city center
$197 nightly
The price is $220 total per night
$220 total
Dec 8 - Dec 9
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.