Cheap Flights to Berkshire County from $49 (2025/2026)

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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.

Tue, Jul 1 - Tue, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 3 hours ago
$98
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Jul 1 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Jul 8, priced at $98 found 3 hours ago
Wed, Jul 23 - Mon, Jul 28
MCO
Orlando Intl.
BDL
Bradley Intl.
$101 Roundtrip, found 2 days ago
$101
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jul 23 from Orlando Intl. to Bradley Intl., returning Mon, Jul 28, priced at $101 found 2 days ago
Mon, Sep 15 - Fri, Sep 19
TPA
Tampa Intl.
BDL
Bradley Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Mon, Sep 15 from Tampa Intl. to Bradley Intl., returning Fri, Sep 19, priced at $102 just found
Mon, Aug 11 - Fri, Aug 15
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$111 Roundtrip, found 12 hours ago
$111
Roundtrip
found 12 hours ago
Select Avelo Airlines flight, departing Mon, Aug 11 from Raleigh - Durham Intl. to Albany Intl., returning Fri, Aug 15, priced at $111 found 12 hours ago
Fri, Sep 5 - Thu, Sep 11
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Raleigh - Durham Intl. to Bradley Intl., returning Thu, Sep 11, priced at $114 found 3 days ago
Thu, Aug 14 - Tue, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$114 Roundtrip, found 10 hours ago
$114
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Thu, Aug 14 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Aug 19, priced at $114 found 10 hours ago
Thu, Aug 28 - Mon, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$148 Roundtrip, found 14 hours ago
$148
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Mon, Sep 1, priced at $148 found 14 hours ago
Wed, Aug 13 - Tue, Aug 19
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, Aug 13 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Aug 19, priced at $157 found 1 day ago
Fri, Sep 26 - Tue, Sep 30
MCO
Orlando Intl.
ALB
Albany Intl.
$157 Roundtrip, found 8 hours ago
$157
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Orlando Intl. to Albany Intl., returning Tue, Sep 30, priced at $157 found 8 hours ago
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 11 to August 18$102
JFKWindsor LocksJune 24 to June 28$137
RSWLathamAugust 21 to August 28$173
JFKLathamJune 25 to June 26$294
MANLathamJune 25 to July 1$941
MANWindsor LocksAugust 4 to August 31$1,135
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksJune 6 to June 8$140
RSWWindsor LocksJune 6 to June 7$200
RSWLathamJune 8 to June 19$481
JFKLathamJune 7 to June 17$638
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Schenectady Downtown
2.5-star property

Hampton Inn Schenectady Downtown

Jul 10 - Jul 13

3 night stay

Cincinnati (CVG) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Cincinnati (CVG)

Delta • Non-stop • Coach
per person
found 13 hours ago
The Equinox Golf Resort & Spa
4.5-star property

The Equinox Golf Resort & Spa

Jul 25 - Jul 27

2 night stay

Detroit (DTW) to Albany (ALB)

Delta • Roundtrip • Coach
per person
found 23 hours ago
DoubleTree by Hilton Schenectady Downtown
4.0-star property

DoubleTree by Hilton Schenectady Downtown

Jul 10 - Jul 13

3 night stay

Cincinnati (CVG) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Cincinnati (CVG)

Delta • Non-stop • Coach
per person
found 13 hours 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! (1,002 reviews)
"Lovely staff!"

Reviewed on May 31, 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! (600 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! (644 reviews)
"Best way to spend a long needed weekend. Can’t wait to do a full week."

Reviewed on Jun 2, 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.