Book Exclusive Berkshire County Vacation Packages

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The Purple Pub with outdoor seating and autumn foliage.

Williamstown

Vacations
Williamstown

Berkshire County 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 CA $1,088, price is now CA $937 per person
CA $937
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf aparthotel 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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $1,713, price is now CA $1,285 per person
CA $1,285
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 Raceway and Saratoga Racetrack are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $1,427, price is now CA $1,162 per person
CA $1,162
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,605, price is now CA $1,335 per person
CA $1,335
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,235, price is now CA $1,058 per person
CA $1,058
per person
Sep 12 - Sep 14
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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.

Stay near popular Berkshire County attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
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Photos of local treasures

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A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.
A waterfall cascading through a rocky gorge with snow patches on the rocks.
A railway track leading into a stone tunnel surrounded by greenery.
A rural landscape with a large red brick building, a smaller beige structure, and a green field.
A forested area with a waterfall cascading over rocks.

Frequently asked questions

How much are vacation packages to Berkshire County?
With vacation packages being sold from just CA $937, you won't need to wipe out your bank balance for your getaway to Berkshire County. Travelocity is here to help. Bundle your flights, hotels and tours into a convenient package and walk away with fantastic discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Berkshire County?
Travelocity has endless ways to score an awesome Berkshire County package deal. Choose from 400 air carriers and 1,000,000 hotels worldwide and create a vacation package that's right for you. With this amount of choice at your fingertips, you'll have plenty of inspiration for your next big adventure.
Why should I book my Berkshire County vacation package via Travelocity?
Incredible savings, countless enticing destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.
Can I save money on my Berkshire County car rental if I bundle it with hotels and flights?
You can with our Berkshire County vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings add up. With a rental car, all the popular attractions around Berkshire County are a fun road trip away.
Which airport is best for Berkshire County?
Bradley Intl. Airport (BDL), Albany Intl. Airport (ALB) and Hartford, CT (HFD-Hartford - Brainard) are the most frequented airports for those traveling in and out of Berkshire County.
What is there to do in Berkshire County?
Berkshire County has hidden gems around every turn, however ensure you visit Williams College and National Shrine of the Divine Mercy while you're here. These landmarks are very popular with visitors to the region.