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The Berkshires Vacation Packages

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The Berkshires Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $483, price is now $383 per person
$383
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this family-friendly aparthotel 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.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $787, price is now $520 per person
$520
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $777, price is now $560 per person
$560
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.

Reviewed on Sep 18, 2026

The Whitlock

The Whitlock

2 out of 5
Price was $740, price is now $537 per person
$537
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Price was $674, price is now $499 per person
$499
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.
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Reviewed on Sep 22, 2026

Hotel On North

Hotel On North

3.5 out of 5
Price was $575, price is now $437 per person
$437
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.

Hill Farm Inn

Hill Farm Inn

4 out of 5
Price was $605, price is now $470 per person
$470
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Arlington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Equinox and Norman Rockwell Exhibition are located nearby.
Our favorite place to stay!!

Reviewed on Aug 11, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $718, price is now $563 per person
$563
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
Beautiful location with a fantastic chef and meal options. Lee the bartender was great, too!

Reviewed on Sep 15, 2026

The Berkshires Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $674, price is now $499 per person
$499
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $787, price is now $520 per person
$520
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $777, price is now $560 per person
$560
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Price was $740, price is now $537 per person
$537
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

The Berkshires Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Latham/Albany Airport

Super 8 by Wyndham Latham/Albany Airport

2 out of 5
Price was $595, price is now $530 per person
$530
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,135, price is now $985 per person
$985
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was $618, price is now $549 per person
$549
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $796, price is now $708 per person
$708
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 14 hours ago
$156
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $156 found 14 hours ago
Allegiant Air
Thu, Oct 15 - Sun, Oct 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$175 Roundtrip, found 11 hours ago
$175
Roundtrip
found 11 hours ago
Select Allegiant Air flight, departing Thu, Oct 15 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Oct 18, priced at $175 found 11 hours ago
American Airlines
Wed, Oct 21 - Wed, Oct 28
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 21 from Ronald Reagan Washington National to Bradley Intl., returning Wed, Oct 28, priced at $180 found 1 day ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $184 found 1 hour ago