Search Deals onThe Berkshires Vacation Packages
The Berkshires Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven
Price was $621, price is now $451 per person
$451
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.
Always great can’t wait to return
Reviewed on Sep 3, 2026
The Cornell Inn, Lenox & The Berkshires
Price was $1,328, price is now $904 per person
$904
per person
Oct 22 - Oct 26
found 1 day 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.
Holiday Inn Club Vacations Oak 'n Spruce Resort
Price was $851, price is now $611 per person
$611
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this ski 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.
The Ponds at Foxhollow
Save 100% on your flight
Price was $956, price is now $695 per person
$695
per person
Oct 22 - Oct 26
found 5 hours ago
Roundtrip flight included
New York (NYC) 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.
Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.
Reviewed on Sep 4, 2026
The Perch Hotel
Price was $2,090, price is now $1,555 per person
$1,555
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.
Vacation Village in the Berkshires
Price was $753, price is now $567 per person
$567
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Saratoga Casino Hotel
Price was $609, price is now $471 per person
$471
per person
Oct 30 - Nov 1
found 16 hours ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.
Hotel charges to much for what they offer
Reviewed on Sep 4, 2026
Pocketbook Hotel and Bath
Price was $1,356, price is now $1,071 per person
$1,071
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Hudson Area 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, Oct 2 - Sun, Oct 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
Thu, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$144 Roundtrip, found 6 hours ago
$144
Roundtrip
found 6 hours ago
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 1 hour ago
$161
Roundtrip
found 1 hour ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$185 Roundtrip, found 3 hours ago
$185
Roundtrip
found 3 hours ago
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