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 $881, price is now CA $700 per person
CA $700
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $2,131, price is now CA $1,700 per person
CA $1,700
per person
Oct 15 - Oct 22
found 22 hours ago
Roundtrip flight included
Halifax (YHZ) 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 Saratoga Racetrack are located nearby.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,006, price is now CA $859 per person
CA $859
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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.
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was CA $1,628, price is now CA $1,420 per person
CA $1,420
per person
Oct 15 - Oct 22
found 22 hours ago
Roundtrip flight included
Halifax (YHZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Clifton Park. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Regal Clifton Park and Wicked Eatery Pub & Entertainment are located nearby.
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
Price was CA $1,490, price is now CA $1,315 per person
CA $1,315
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park 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
The price is CA $131 per night
CA $131
CA $161 total
Aug 12 - Aug 13
includes taxes & fees
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.
Pool
Parking included
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 $199 per night
CA $199
CA $223 total
Aug 5 - Aug 6
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.
Pool
Hot tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is CA $150 per night
CA $150
CA $199 total
Aug 30 - Aug 31
includes taxes & fees
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.
Pool
Hot tub
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
The price is CA $87 per night
CA $87
CA $97 total
Aug 5 - Aug 6
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.
Parking included
Free WiFi
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is CA $202 per night
CA $202
CA $226 total
Sep 3 - Sep 4
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.
Pet-friendly
Parking included
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
The price is CA $201 per night
CA $201
CA $224 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
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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.
See properties

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 $700, 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.