Book Exclusive Berkshire County Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Berkshire County's top destinations

Williamstown

Vacations
Williamstown

Berkshire County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
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 $914, price is now CA $784 per person
CA $784
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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 Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $1,261, price is now CA $976 per person
CA $976
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,035, price is now CA $852 per person
CA $852
per person
Aug 4 - Aug 7
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $907, price is now CA $795 per person
CA $795
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Berkshires Untold

Berkshires Untold

3.5 out of 5
Price was CA $1,113, price is now CA $998 per person
CA $998
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Albany (ALB)
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

Top Berkshire County hotels deals

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 $121 per night
CA $121
CA $166 total
May 25 - May 26
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.
Pool
Hot tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $165 total
May 25 - May 26
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
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 $119 per night
CA $119
CA $148 total
May 25 - May 26
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.
Pool
Parking included
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 $210 per night
CA $210
CA $234 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub
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 $215 per night
CA $215
CA $302 total
May 31 - Jun 1
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 Tanglewood Music Center and Schantz Galleries are located nearby.
Pool
Spa
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is CA $150 per night
CA $150
CA $168 total
May 25 - May 26
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.
Don't see what you're looking for?
See all available properties in Berkshire County
View all properties
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.

Photos of local treasures

Browse Berkshire County vacation photos for more inspiration

Historic Shaker village
Berkshire County
Berkshire County
Berkshire County
Berkshire County

Frequently asked questions

How much are vacation packages to Berkshire County?
With vacation packages being sold from just CA $784, 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.