The Berkshires Vacation Packages

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Your The Berkshires Vacation

Leave the travel planning to us with a The Berkshires vacation package. With everything organized before you head off, the only thing left for you to do is relax and enjoy this destination's countless delights. A trip to The Berkshires wouldn't be complete without exploring some of its most renowned cities, starting with Lenox. A couple of the top attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown should also be on the itineraries of all The Berkshires travellers. Visitors to this city enjoy Massachusetts Museum of Contemporary Art and Mount Greylock. Expedia has flights, hotels, car rentals and more to help you organize your own customized The Berkshires vacation today.

Top The Berkshires Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales

Valley Craft Ales

2 out of 5
Price was CA $1,203, price is now CA $1,015 per person
CA $1,015
per person
Oct 12 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very Good! (145 reviews)
Very convenient location.

Reviewed on Aug. 29, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,743, price is now CA $1,355 per person
CA $1,355
per person
Oct 12 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,683, price is now CA $1,416 per person
CA $1,416
per person
Oct 12 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (220 reviews)
The room we stayed in was comfortable and had a great view from the balcony. The bed was very comfortable. I would have liked more space in the bathroom to put a cup and other things. Also, an exhaust fan would be nice in the bathroom. But it was pretty. The staff were all very gracious. We had a good meal Sunday night in the restaurant and our waiter was very nice. I knew that the restaurant would not be open on Monday and Tuesday, but it would have been nice to have the bar open for drinks on the patio in the evening on those nights.

Reviewed on Jul. 24, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was CA $1,417, price is now CA $1,233 per person
CA $1,233
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (512 reviews)
Nothing additional to add

Reviewed on Aug. 28, 2025

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was CA $1,175, price is now CA $1,077 per person
CA $1,077
per person
Oct 12 - Oct 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (582 reviews)
Quiet, clean rooms very convenient to town center and the green mountain bluegrass festival. Would definitely stay here again.

Reviewed on Aug. 15, 2025

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The Berkshires Hotel Deals

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Sep 17 to Sep 18
CA $212
CA $237 total
Sep 17 - Sep 18
includes taxes & fees
Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Sep 11 to Sep 12
CA $147
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
Berkshire Mountain Lodge
See all 1,104 properties in The Berkshires
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.
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Discover the most popular places to visit in The Berkshires

Norman Rockwell Museum

Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Naumkeag Museum

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.