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The Berkshires Vacation Packages

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The Berkshires which includes snow and snow boarding

The Berkshires
Massachusetts
United States of America
North America
Hotwire.com

The Berkshires Flight + Hotel Packages

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

Marriott Albany

3.5 out of 5

Price was $447, price is now $347 per person

$347

per person

Jan 15 - Jan 18

found 10 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy an outdoor pool, a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5

Save 100% on your flight

Price was $1,320, price is now $829 per person

$829

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located nearby.

Prospect Berkshires

3 out of 5

Price was $1,324, price is now $902 per person

$902

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip 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 Cornell Inn, Lenox & The Berkshires

3.5 out of 5

Save 100% on your flight

Price was $993, price is now $714 per person

$714

per person

Dec 27 - Dec 31

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 The Bookstore and Lenox Library are located nearby.

Vacation Village in the Berkshires

3 out of 5

Price was $794, price is now $629 per person

$629

per person

Dec 27 - Dec 31

found 1 day 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.

Pocketbook Hotel and Bath

2 out of 5

Price was $881, price is now $700 per person

$700

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.

Berkshire Mountain Lodge

3 out of 5

Price was $602, price is now $486 per person

$486

per person

Dec 27 - Dec 31

found 1 day 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 Guido's Marketplace and Herman Melville's Arrowhead are located nearby.

The Landing Hotel at Rivers Casino & Resort

4 out of 5

Price was $701, price is now $567 per person

$567

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) 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 Scene One Movieland are located nearby.