Search Deals onThe Berkshires Vacation Packages
The Berkshires Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Save 100% on your flight
Price was $970, price is now $703 per person
$703
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop 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 Cornell Inn, Lenox & The Berkshires
Save 100% on your flight
Price was $3,815, price is now $2,691 per person
$2,691
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop 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.
The Equinox Golf Resort & Spa
Price was $1,388, price is now $1,005 per person
$1,005
per person
Jul 9 - Jul 13
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Save 100% on your flight
Price was $4,481, price is now $3,268 per person
$3,268
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this cottage in Austerlitz. Enjoy balconies, in-room washers/dryers, and in-room fireplaces. Popular attraction Art et Industrie is located nearby.
The Landing Hotel at Rivers Casino & Resort
Save 100% on your flight
Price was $1,207, price is now $899 per person
$899
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Prospect Berkshires
Save 100% on your flight
Price was $2,421, price is now $1,846 per person
$1,846
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
The Brooks Motel
Save 100% on your flight
Price was $1,075, price is now $836 per person
$836
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Catamount Aerial Adventure Park and Community Library are located nearby.
The White House Inn
Save 100% on your flight
Price was $1,066, price is now $834 per person
$834
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
The Berkshires Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
The Berkshires Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Jun 5 - Sat, Jun 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Tue, Jun 9 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Tue, Jun 9 - Wed, Jun 10
MCO
Orlando Intl.
ALB
Albany Intl.
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
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