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.

Thu, Feb 5 - Sun, Feb 8
MCO
Orlando
BDL
Hartford
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Orlando to Hartford, returning Sun, Feb 8, priced at $68 found 6 days ago
Thu, Jan 29 - Sun, Feb 1
TPA
Tampa
BDL
Hartford
$123 Roundtrip, found 4 days ago
$123
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jan 29 from Tampa to Hartford, returning Sun, Feb 1, priced at $123 found 4 days ago
Thu, Feb 26 - Tue, Mar 3
ATL
Atlanta
BDL
Hartford
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Atlanta to Hartford, returning Tue, Mar 3, priced at $128 found 6 days 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
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
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.
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
36.81 mi from city center
$122 nightly
The price is $137 total per night
$137 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and 3 minutes by foot from Mohawk Theater.
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
$219 nightly
The price is $245 total per night
$245 total
Jan 1 - Jan 2, 2026
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.
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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.