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.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was CA $1,138, price is now CA $1,095 per person
CA $1,095
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,904, price is now CA $1,732 per person
CA $1,732
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was CA $1,611, price is now CA $1,515 per person
CA $1,515
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Weathervane Motel

Weathervane Motel

2 out of 5
Price was CA $1,283, price is now CA $1,227 per person
CA $1,227
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this motel in Manchester Center. Enjoy free WiFi, daily housekeeping, and satellite TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hildene and Equinox Preservation Trust are located nearby.
Knotty Pine

Knotty Pine

2.5 out of 5
Price was CA $1,446, price is now CA $1,402 per person
CA $1,402
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bennington Museum and Old First Congregational Church 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 20 - Jul 21
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 MCLA Gallery 51 and North Adams Center 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 5 - Aug 6
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 $239 per night
CA $239
CA $267 total
Jul 19 - Jul 20
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 $256 per night
CA $256
CA $349 total
Jul 27 - Jul 28
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 $1,095, 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.