
Cheap Flights to Berkshire County from $28 (2026/2027)
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
Jet to one of Berkshire County's top cities

Lenox
Flights
How Much Does it Cost To Fly To Berkshire County?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
MCO
Orlando Intl.
BDL
Bradley Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
TPA
Tampa Intl.
BDL
Bradley Intl.
$131 Roundtrip, just found
$131
Roundtrip
just found
MCO
Orlando Intl.
ALB
Albany Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$146 Roundtrip, found 6 days ago
$146
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | February 21 to February 23 | $100 |
| RSW | Windsor Locks | March 6 to March 9 | $147 |
| RSW | Latham | April 18 to April 25 | $214 |
| JFK | Latham | February 26 to March 4 | $271 |
| MAN | Windsor Locks | March 5 to March 18 | $820 |
| MAN | Latham | March 4 to March 18 | $991 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | February 15 to February 19 | $183 |
| RSW | Windsor Locks | February 14 to March 2 | $223 |
| RSW | Latham | February 14 to February 19 | $290 |
| JFK | Latham | February 15 to February 16 | $746 |
| MAN | Windsor Locks | February 15 to February 19 | $1,402 |
Best Berkshire County Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



Don't see what you're looking for?
See all available trips from San Juan to Berkshire County
View all tripsTravelers ❤️ These Berkshire County 🏨

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
8.6/10 Excellent! (2,221 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.
Reviewed on Jan 25, 2026

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
8.8/10 Excellent! (1,003 reviews)
Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel.
Reviewed on Feb 1, 2026

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
9/10 Wonderful! (826 reviews)
Room was clean and nicely equipped with kitchen. Will return if the future.
Reviewed on Feb 1, 2026
Save an average of 15% on thousands of hotels when you're signed in

The Williams Inn
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.
9.6/10 Exceptional! (572 reviews)
Clean
Reviewed on Jan 31, 2026
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.







