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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.
Motel 6 Schenectady, NY

Motel 6 Schenectady, NY

2 out of 5
Price was $751, price is now $527 per person
$527
per person
Nov 29 - Dec 3
found 8 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this motel in Schenectady. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Rollarama Skating Center and Central Park Tennis Center are located nearby.

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,547, price is now $1,126 per person
$1,126
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,444, price is now $1,091 per person
$1,091
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026

South Shire

South Shire

4 out of 5
Price was $1,239, price is now $952 per person
$952
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
We love it ♥️

Reviewed on Oct 6, 2026

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $940, price is now $784 per person
$784
per person
Nov 26 - Nov 30
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Racetrack and Saratoga Performing Arts Center are located nearby.

The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ

The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ

3 out of 5
Price was $1,697, price is now $1,431 per person
$1,431
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
Stay at this cottage in Catskill. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Thomas Cole National Historic Site and Avalon Lounge are located nearby.

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $2,364, price is now $2,000 per person
$2,000
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
Stay at this cottage in Earlton. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Thunderhart Golf Course and Cairo Lockwood State Forest are located nearby.

The Berkshires Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Albany

Howard Johnson by Wyndham Albany

2 out of 5
Colonie
Price was $726, price is now $519 per person
$519
per person
Nov 29 - Dec 3
found 8 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Motel 6 Schenectady, NY

Motel 6 Schenectady, NY

2 out of 5
Price was $751, price is now $527 per person
$527
per person
Nov 29 - Dec 3
found 8 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $940, price is now $784 per person
$784
per person
Nov 26 - Nov 30
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)

The Berkshires Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,015, price is now $866 per person
$866
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,547, price is now $1,126 per person
$1,126
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,444, price is now $1,091 per person
$1,091
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
South Shire

South Shire

4 out of 5
Price was $1,239, price is now $952 per person
$952
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) 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, Nov 13 - Wed, Dec 2
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 13 from Luis Munoz Marin Intl. to Bradley Intl., returning Wed, Dec 2, priced at $115 just found
Allegiant Air
Sun, Oct 25 - Sun, Nov 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$162 Roundtrip, found 9 hours ago
$162
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Sun, Oct 25 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Nov 1, priced at $162 found 9 hours ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$174 Roundtrip, just found
$174
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $174 just found
Breeze Airways
Wed, Dec 2 - Tue, Dec 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 2 from Orlando Intl. to Bradley Intl., returning Tue, Dec 8, priced at $179 found 1 day ago