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, May 7 - Mon, May 11
MCO
Orlando
BDL
Hartford
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando to Hartford, returning Mon, May 11, priced at $100 found 6 days ago
Fri, Apr 10 - Mon, Apr 13
ATL
Atlanta
BDL
Hartford
$114 Roundtrip, found 5 days ago
$114
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Atlanta to Hartford, returning Mon, Apr 13, priced at $114 found 5 days ago
Thu, May 7 - Fri, May 29
MCO
Orlando
ALB
Albany
$141 Roundtrip, found 5 days ago
$141
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando to Albany, returning Fri, May 29, priced at $141 found 5 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
$119 nightly
The price is $133 total per night
$133 total
Mar 9 - Mar 10
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
36.78 mi from city center
$118 nightly
The price is $132 total per night
$132 total
Mar 31 - Apr 1
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 North Adams City Hall.
Pool
Hot Tub
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
$115 nightly
The price is $128 total per night
$128 total
Apr 6 - Apr 7
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
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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.