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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $838, price is now CA $708 per person
CA $708
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Calgary (YYC) 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.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was CA $1,270, price is now CA $1,012 per person
CA $1,012
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this family-friendly 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 National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $1,117, price is now CA $913 per person
CA $913
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Calgary (YYC) 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 Tanglewood Music Center and Guido's Marketplace are located nearby.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,132, price is now CA $971 per person
CA $971
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Calgary (YYC) 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.
Hotel On North

Hotel On North

3.5 out of 5
Price was CA $1,378, price is now CA $1,199 per person
CA $1,199
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.

Top Berkshire County hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free cancellation
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
CA $210 total
Jul 19 - Jul 20
includes taxes & fees
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.
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free cancellation
The price is CA $226 per night
CA $226
CA $252 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and MCLA Gallery 51 are located nearby.
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
The price is CA $166 per night
CA $166
CA $185 total
Aug 6 - Aug 7
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $213 per night
CA $213
CA $238 total
Jul 21 - Jul 22
includes taxes & fees
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $188 per night
CA $188
CA $241 total
Aug 16 - Aug 17
includes taxes & fees
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 Tanglewood Music Center and Guido's Marketplace are located nearby.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $250 per night
CA $250
CA $342 total
Jul 23 - Jul 24
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Browse Berkshire County vacation photos for more inspiration

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 $708, 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.