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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $842, price is now $631 per person
$631
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,708, price is now $1,181 per person
$1,181
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 The Bookstore are located nearby.
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
Save 100% on your flight
Price was $1,137, price is now $790 per person
$790
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this 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 National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $860, price is now $632 per person
$632
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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.
The Whitlock

The Whitlock

2 out of 5
Save 100% on your flight
Price was $1,398, price is now $1,032 per person
$1,032
per person
Jun 19 - Jun 26
found 24 hours 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 The Bookstore are located nearby.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $963, price is now $732 per person
$732
per person
Jul 27 - Jul 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,092, price is now $837 per person
$837
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $940, price is now $722 per person
$722
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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.

The Berkshires Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
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
Price was $852, price is now $650 per person
$650
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $2,325, price is now $1,509 per person
$1,509
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $963, price is now $732 per person
$732
per person
Jul 27 - Jul 31
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,092, price is now $837 per person
$837
per person
Aug 7 - Aug 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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $842, price is now $631 per person
$631
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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
Save 100% on your flight
Price was $1,137, price is now $790 per person
$790
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $860, price is now $632 per person
$632
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Save 100% on your flight
Price was $1,398, price is now $1,032 per person
$1,032
per person
Jun 19 - Jun 26
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

Top Flight Deals

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

Frontier Airlines
Fri, May 29 - Sat, May 30
MCO
Orlando Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 29 from Orlando Intl. to Bradley Intl., returning Sat, May 30, priced at $98 found 2 days ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 4 hours ago
$174
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $174 found 4 hours ago
American Airlines
Sat, Jun 6 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 6 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Jun 16, priced at $191 found 1 day ago
Frontier Airlines
Thu, May 21 - Sun, May 24
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 21 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, May 24, priced at $196 found 2 days ago