Cheap Flights to Berkshire County from $50 (2025/2026)

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Lenox which includes an administrative buidling

Lenox

Flights
Lenox

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.

Fri, Jul 18 - Mon, Jul 21
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, Jul 18 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jul 21, priced at $98 found 1 hour ago
Fri, Sep 5 - Mon, Sep 8
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$111 Roundtrip, found 23 hours ago
$111
Roundtrip
found 23 hours ago
Select Avelo Airlines flight, departing Fri, Sep 5 from Raleigh - Durham Intl. to Albany Intl., returning Mon, Sep 8, priced at $111 found 23 hours ago
Tue, Jul 22 - Tue, Jul 29
MCO
Orlando Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 3 hours ago
$112
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Tue, Jul 22 from Orlando Intl. to Bradley Intl., returning Tue, Jul 29, priced at $112 found 3 hours ago
Fri, Sep 5 - Thu, Sep 11
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$114 Roundtrip, found 2 hours ago
$114
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Raleigh - Durham Intl. to Bradley Intl., returning Thu, Sep 11, priced at $114 found 2 hours ago
Sat, Jun 14 - Sat, Jun 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$148 Roundtrip, found 4 hours ago
$148
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Orlando Intl. to Bradley Intl., returning Sat, Jun 14, priced at $148 found 4 hours ago
Thu, Sep 4 - Sun, Sep 7
MCO
Orlando Intl.
ALB
Albany Intl.
$156 Roundtrip, found 2 days ago
$156
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Sun, Sep 7, priced at $156 found 2 days ago
Wed, Jul 9 - Tue, Jul 22
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 9 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Jul 22, priced at $157 found 1 day ago
Tue, Aug 12 - Tue, Aug 19
MCO
Orlando Intl.
ALB
Albany Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Albany Intl., returning Tue, Aug 19, priced at $157 found 1 day ago
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 11 to August 18$102
JFKWindsor LocksJune 28 to July 2$137
RSWLathamAugust 21 to August 28$165
JFKLathamJune 25 to June 26$294
MANLathamJune 25 to July 1$941
MANWindsor LocksSeptember 10 to October 3$962
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksJune 6 to June 8$140
RSWWindsor LocksJune 6 to June 9$160
JFKLathamJune 8 to June 15$325
RSWLathamJune 8 to June 19$481
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites by Wyndham Amsterdam
2.5-star property

Microtel Inn & Suites by Wyndham Amsterdam

Jun 18 - Jun 21

3 night stay

Little Rock (LIT) to Albany (ALB)

Delta • Non-stop • Coach

Albany (ALB) to Little Rock (LIT)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Hotel Brookmere & Arbor Spa
4.0-star property

Hotel Brookmere & Arbor Spa

Jun 18 - Jun 21

3 night stay

Little Rock (LIT) to Albany (ALB)

Delta • Non-stop • Coach

Albany (ALB) to Little Rock (LIT)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Gideon Putnam Resort And Spa
4.0-star property

Gideon Putnam Resort And Spa

Jun 18 - Jun 21

3 night stay

Little Rock (LIT) to Albany (ALB)

Delta • Non-stop • Coach

Albany (ALB) to Little Rock (LIT)

American Airlines • Non-stop • Coach
per person
found 1 day ago
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Travelers ❤️ These Berkshire County 🏨

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
9/10 Wonderful! (1,001 reviews)
"Nice place thought still under construction."

Reviewed on May 29, 2025

The Yankee, Trademark Collection by Wyndham
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
8.2/10 Very Good! (1,001 reviews)
"Clean rooms and friendly staff. Conveniently located as well!"

Reviewed on May 27, 2025

Quality Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star 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! (598 reviews)
"Great spot for hitting hiking spots"

Reviewed on May 27, 2025

Berkshires Untold
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
9/10 Wonderful! (642 reviews)
"Good value"

Reviewed on May 26, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Destinations in Berkshire County

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.