
Flights To Berkshire County - Cheap Flights Starting at CA $96
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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.
CA $198 Roundtrip, found 11 hours ago
CA $198
Roundtrip
found 11 hours ago
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $218 Roundtrip, found 2 days ago
CA $218
Roundtrip
found 2 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $222 Roundtrip, found 2 days ago
CA $222
Roundtrip
found 2 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $225 Roundtrip, found 2 days ago
CA $225
Roundtrip
found 2 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $229 Roundtrip, found 2 days ago
CA $229
Roundtrip
found 2 days ago
MCO
Orlando Intl.
ALB
Albany Intl.
CA $291 Roundtrip, found 3 days ago
CA $291
Roundtrip
found 3 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $326 Roundtrip, found 2 days ago
CA $326
Roundtrip
found 2 days ago
SAN
San Diego Intl.
BDL
Bradley Intl.
CA $332 Roundtrip, found 2 days ago
CA $332
Roundtrip
found 2 days ago
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $640 Roundtrip, found 4 days ago
CA $640
Roundtrip
found 4 days ago
YYC
Calgary Intl.
ALB
Albany Intl.
CA $666 Roundtrip, found 1 day ago
CA $666
Roundtrip
found 1 day ago
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $711 Roundtrip, found 1 day ago
CA $711
Roundtrip
found 1 day ago
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| JFK | Windsor Locks | June 7 to June 10 | CA $269 |
| RSW | Windsor Locks | July 28 to August 4 | CA $375 |
| RSW | Latham | July 10 to July 17 | CA $801 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| RSW | Windsor Locks | May 30 to May 31 | CA $308 |
Price found within the past 48 hours. Click for updated prices.



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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 Tanglewood Music Center and Guido's Marketplace are located nearby.
9/10 Wonderful! (946 reviews)
"The stay was great . No complains at all . Definitely will be staying in the near future ."
Reviewed on May 22, 2026

Berkshires Untold
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
9/10 Wonderful! (958 reviews)
"The hotel was funky is a good way, I liked the design and layout of the room and the dining area."
Reviewed on May 23, 2026

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.
8.8/10 Excellent! (2,364 reviews)
"The room was clean and spacious. The kitchen was equipped with all necessary supplies to cook a full meal. Great place to stay and relax or plan family fun!"
Reviewed on May 24, 2026
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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)
"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"
Reviewed on May 23, 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.






